Description Reference
ChemicalBook > CAS DataBase List > 2,3,4,6-Tetrakis-O-trimethylsilyl-D-gluconolactone

2,3,4,6-Tetrakis-O-trimethylsilyl-D-gluconolactone

Description Reference
Product Name
2,3,4,6-Tetrakis-O-trimethylsilyl-D-gluconolactone
CAS No.
32384-65-9
Chemical Name
2,3,4,6-Tetrakis-O-trimethylsilyl-D-gluconolactone
Synonyms
2,3,4,6-Tetrakis-O-trimethylsilyl-D-gluconolactone;D-Gluconic acid, 2,3,4,6-tetrakis-O-(triMethylsilyl)-, δ-lactone;Dagliptin Impurity;oxy)-6-((triMethyL;Cagliflozin Impurity 9;Englitazinintermediate;Dapagliflozin Impurity 12;Canagliflozin Related Impurity 9;(3R,4S,5R,6R)-3,4,5-tris(triMethyL;Canagliflozin Impurity 9(Dagelin impurity 11)
CBNumber
CB32610563
Molecular Formula
C18H42O6Si4
Formula Weight
466.87
MOL File
32384-65-9.mol
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2,3,4,6-Tetrakis-O-trimethylsilyl-D-gluconolactone Property

Boiling point:
417℃
Density 
0.97
Flash point:
171℃
storage temp. 
under inert gas (nitrogen or Argon) at 2-8°C
solubility 
Chloroform (Sparingly), Ethyl Acetate (Slightly), Methanol (Slightly)
form 
Oil
color 
Colourless to Pale Yellow
Stability:
Moisture Sensitive
InChI
InChI=1/C18H42O6Si4/c1-25(2,3)20-13-14-15(22-26(4,5)6)16(23-27(7,8)9)17(18(19)21-14)24-28(10,11)12/h14-17H,13H2,1-12H3/t14-,15-,16+,17-/s3
InChIKey
VNGTZLYNGGLPIZ-NELUYGJANA-N
SMILES
O([C@@H]1[C@H](C(=O)O[C@H](CO[Si](C)(C)C)[C@H]1O[Si](C)(C)C)O[Si](C)(C)C)[Si](C)(C)C |&1:1,2,6,13,r|
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Safety

HS Code 
2931900090
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

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N-Bromosuccinimide Price

TRC
Product number
T279540
Product name
2,3,4,6-Tetrakis-O-trimethylsilyl-D-gluconolactone
Packaging
5g
Price
$65
Updated
2021/12/16
TRC
Product number
T279540
Product name
2,3,4,6-Tetrakis-O-trimethylsilyl-D-gluconolactone
Packaging
50g
Price
$185
Updated
2021/12/16
Biosynth Carbosynth
Product number
MT08101
Product name
2,3,4,6-Tetra-O-trimethylsilyl-D-glucono-1,5-lactone
Packaging
100g
Price
$250
Updated
2021/12/16
ChemScene
Product number
CS-M2269
Product name
(3R,4S,5R,6R)-3,4,5-Tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one
Purity
>97.0%
Packaging
500g
Price
$321
Updated
2021/12/16
Biosynth Carbosynth
Product number
MT08101
Product name
2,3,4,6-Tetra-O-trimethylsilyl-D-glucono-1,5-lactone
Packaging
250g
Price
$375
Updated
2021/12/16
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2,3,4,6-Tetrakis-O-trimethylsilyl-D-gluconolactone Chemical Properties,Usage,Production

Description

It is usually used as the intermediate and raw material in the chemistry synthesis and pharmaceutical industry. Especially, this chemical has been widely used in the design and synthesis of sodium-glucose transporter inhibitors.1 For example, this substance can be employed as raw material in the preparation of (1s)-1,5-anhydro-1-c-[4-chloro-3-[(4-ethoxylphenyl)methyl]phenyl]-D-glucitol, which is commonly known as Dapagliflozin that act as the sodium dependent glucose transporters for treating type 2 diabetes.2 Moreover, it can also function as the intermediate for synthesizing empagliflozin, which is a novel and selective sodium glucose co-transporter-2 inhibitor.3 In addition, canagliflozin, another sodium glucose co-transporter-2 inhibitor, can be obtained by utilizing this substance as the intermediate.4

Reference

  1. Guo, C.; Hu, M.; DeOrazio, R. J.; Usyatinsky, A.; Fitzpatrick, K.; Zhang, Z. J.; Maeng, J. H.; Kitchen, D. B.; Tom, S.; Luche, M.; Khmelnitsky, Y.; Mhyre, A. J.; Guzzo, P. R.; Liu, S., The design and synthesis of novel SGLT2 inhibitors: C-glycosides with benzyltriazolopyridinone and phenylhydantoin as the aglycone moieties. Bioorg. Med. Chem. 2014, 22, 3414-3422.
  2. S Thirumalai Rajan; Eswaraiah, S., Process for the preparation of (1S)-1,5-anhydro-1-C-[4-chloro-3-[(4-ethoxylphenyl)methyl]phenyl]-D-glucitol and its solvate thereof. US Patent 2015, WO 2015/132803 A2.
  3. Hrapchak, M.; Latli, B.; Wang, X. J.; Lee, H.; Campbell, S.; Song, J. J.; Senanayake, C. H., Synthesis of empagliflozin, a novel and selective sodium-glucose co-transporter-2 inhibitor, labeled with carbon-14 and carbon-13. J. Label. Compd. Radiopharm. 2014, 57, 687-694.
  4. Nomura, S.; Sakamaki, S.; Hongu, M.; Kawanishi, E.; Koga, Y.; Sakamoto, T.; Yamamoto, Y.; Ueta, K.; Kimata, H.; Nakayama, K.; Tsuda-Tsukimoto, M., Discovery of Canagliflozin, a Novel C-Glucoside with Thiophene Ring, as Sodium-Dependent Glucose Cotransporter 2 Inhibitor for the Treatment of Type 2 Diabetes Mellitus. J. Med. Chem. 2010, 53, 6355-6360.

Chemical Properties

Pale yellow oil

Uses

2,3,4,6-Tetrakis-O-trimethylsilyl-D-gluconolactone is an antidiabetic agent and an intermediate of Dapagliflozin (D185370). 2,3,4,6-Tetrakis-O-trimethylsilyl-D-gluconolactone acts as a reagent in the synthesis of trans-cyclohexane-bearing C-glucose as sodium glucose co-transporter 2 inhibitors.

Synthesis

At present, the publicly reported synthesis process of 2,3,4,6-Tetrakis-O-trimethylsilyl-D-gluconolactone is mainly prepared by the synthesis of D-gluconolactone and trimethylsilyl chloride in the presence of an acid-binding agent or the preparation of D-gluconolactone and hexamethyldisilazane in dichloromethane reflux. The former has problems such as high pH requirements, low atom economy, and severe pollution. In contrast, the latter has such problems as the large amount of hexamethyldisilazane used, the strong volatility of dichloroethane, and severe pollution. Therefore, Li et al. developed a method for preparing 2,3,4,6-Tetrakis-O-trimethylsilyl-D-gluconolactone, comprising the following operations: reacting D-gluconolactone with hexamethyldisilazane in an ionic liquid at standard pressure, and removing the ionic liquid by reduced pressure distillation after the reaction is completed to obtain 2,3,4,6-Tetrakis-O-trimethylsilyl-D-gluconolactone; the cation in the ionic liquid is an alkyl imidazolium ion, and the anion in the ionic liquid is hexafluorophosphate, tetrafluoroborate, tetrachloroaluminate or chloride ion.

2,3,4,6-Tetrakis-O-trimethylsilyl-D-gluconolactone Preparation Products And Raw materials

Raw materials

Preparation Products

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2,3,4,6-Tetrakis-O-trimethylsilyl-D-gluconolactone Suppliers

Australia 1 China 429 India 37 United Kingdom 3 United States 10 Global 480
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View Lastest Price from 2,3,4,6-Tetrakis-O-trimethylsilyl-D-gluconolactone manufacturers

Baoji Guokang Bio-Technology Co., Ltd.
Product
(3R,4S,5R,6R)-3,4,5-tris(triMethylsilyloxy)-6-((triMethylsilyloxy)Methyl)tetrahydro-2H-pyran-2-one 32384-65-9
Price
US $412.00/g
Min. Order
100g
Purity
99%
Supply Ability
1kg
Release date
2021-06-04
Nanjing Fred Technology Co., Ltd
Product
(3R,4S,5R,6R)-3,4,5-tris(triMethylsilyloxy)-6-((triMethylsilyloxy)Methyl)tetrahydro-2H-pyran-2-one 32384-65-9
Price
US $0.00-0.00/kg
Min. Order
1kg
Purity
98%
Supply Ability
1 ton
Release date
2024-01-02
Hebei Weibang Biotechnology Co., Ltd
Product
(3R,4S,5R,6R)-3,4,5-tris(triMethylsilyloxy)-6-((triMethylsilyloxy)Methyl)tetrahydro-2H-pyran-2-one 32384-65-9
Price
US $10.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
10 mt
Release date
2024-11-21

32384-65-9, 2,3,4,6-Tetrakis-O-trimethylsilyl-D-gluconolactoneRelated Search:

2-(5-BroMo-2-Methylbenzyl)-5-(4-fluorophenyl)thiophene 5-bromo-2-chloro-4’-ethoxydiphenylmethane (R)-3-(4-(5-broMo-2-chlorobenzyl)phenoxy)tetrahydrofuran 4-(5-broMo-2-chlorobenzyl)phenol Acarbose 5-Bromo-2-methylbenzoic acid D-Glucitol, 1,5-anhydro-1-C-[3-[[5-(4-fluorophenyl)-2-thienyl]Methyl]-4-Methylphenyl]-, tetraacetate, (1S)- (9CI) (5-broMo-2-Methylphenyl)(5-(4-fluorophenyl)thiophen-2-yl)Methanone 2-(4-Fluorophenyl)-5-[(5-iodo-2-methylphenyl)methyl]thiophene 5-Bromo-2-methylbenzoyl chloride 5-Iodo-2-methylbenzoic acid Canagliflozin heMihydrate LIPOPHILIC SEPHADEX 2-(4-Fluorophenyl)-thiophene BCP19353 Canagliflozin 5-Bromo-2-chlorobenzoic acid (5-broMo-2-chlorophenyl)(2-ethoxyphenyl)Methanone

  • (3R,4S,5R,6R)-3,4,5-tris(triMethylsilyloxy)-6-((triMethylsilyloxy)Methyl)tetrahydro-2H-pyran-2-one
  • (3R,4S,5R,6R)-3,4,5-Tris[(trimethylsilyl)oxy]-6-[[(trimethylsilyl)oxy]methyl]tetrahydropyran-2-one
  • 2,3,4,6-Tetrakis-O-trimethylsilyl-D-gluconolactone
  • D-2,3,4,6-Tetrakis-O-(trimethylsilyl)-gluconic acid delta-lactone
  • D-Gluconic acid, 2,3,4,6-tetrakis-O-(triMethylsilyl)-, δ-lactone
  • 2,3,4,6-Tetrakis-O-triMethylsilyl-D-gluconolactoe
  • D-Gluconic acid, 2,3,4,6-tetrakis-O-(triMethylsilyl)-, d-lactone
  • 2,3,4,6-tetrakis-O-trimethylsilyl-D-glucono1,5 lactone
  • (3R,5R,6R)-3,4,5-Tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one
  • (3R,4S,5R,6R)-3,4,5-tris(trimethylsilyloxy)-6-(trimethylsilyloxymethyl)oxan-2-one
  • 2,3,4,6-Tetra-O-(trimethylsilyl)-D-glucono-1,5-lactone
  • Dapagliflozin Impurity 12
  • Cagliflozin Impurity 9
  • 32384-65-9 2,3,4,6-Tetrakis-O-trimethylsilyl-D-gluconolactone
  • (3R,4S,5R,6R)-3,4,5-tris(trimethylsilyloxy)-6-(trimethylsilyloxymethyl)oxan-2-one 32384-65-9
  • (3R,4S,5R,6R)-3,4,5-tris(trimethylsilyl)oxy)-6-((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one 97%
  • 2,3,4,6-Tetra-O-(trimethylsilyl)-D-glucono-delta-lactone
  • (3R,4S,5R,6R)-3,4,5-tris(trimethylsilyloxy)-6-(trimethylsilyloxymethyl)oxan
  • Dagliptin Impurity
  • (3R,4S,5R,6R)-3,4,5-tris(triMethyL
  • oxy)-6-((triMethyL
  • Canagliflozin Related Impurity 9
  • 2,3,4,6, tetrakis-O-(trimethylsilyl)-D-lactone,
  • 2,3,4,6-Tetrakis-O-trimethylsilyl-D-gluconolactone(For export only)
  • (3R,4S,5R,6R)-3,4,5-tris(triMethylsilyloxy)-6-((triMethylsilyloxy)Methyl)tetrahydro-2H-pyran-2-one ISO 9001：2015 REACH
  • Empagliflozin intermediates，2,3,4,6-Tetrakis-O-trimethylsilyl-D- gluconolactone
  • 2,3,4,5-Tetrakis-O-trimethylsilyl-D-gluconolactone
  • 5-tris(triMethylsilyloxy)-6-((triMethylsilyloxy)Methyl)tetrahydro-2H-pyran-2-one
  • D-Gluconic acid, 2,3,4,6-tetrakis-O-(trimethylsilyl)-, .delta.-lactone
  • 2,3,4,6-Tetra-O-(trimethylsilyl)-D-glucono-1,5-lactoneQ: What is 2,3,4,6-Tetra-O-(trimethylsilyl)-D-glucono-1,5-lactone Q: What is the CAS Number of 2,3,4,6-Tetra-O-(trimethylsilyl)-D-glucono-1,5-lactone Q: What is the storage condition of 2,3,4,6-Tetra-O-(trimethylsilyl)-D-glucono-1,5-lactone Q: What are the applications of 2,3,4,6-Tetra-O-(trimethylsilyl)-D-glucono-1,5-lactone
  • 3,4,5-Tris[(trimethyl silyl)oxy]-6-{[(trimethylsilyl)oxy]methyl}tetrahydro-2H-pyron-2-one
  • Englitazinintermediate
  • Boronicacid,B-(1,6-dihydro-6-oxo-9-pyridinyl)-
  • (3R,4S,5R,6R)-3,4,5-tri ((trimethyl) Methylsilane)oxy)-6-(((trimethylmethylmethyl Silic alkyl)oxy group) field group) four atmosphere-2H-pyrid N?m-2-ketone
  • (3R, 4S, 5R, 6R)-3,4,5-tri ((trimethyl)Methylsilane)oxy)-6-(((trimethylmethylmethyl Silicyl)oxy)methyl)tetrahydr-2H-pyridium N?m-2-ketone
  • (3R,4S,5R,6R)-3,4,5-tris(triMethylsilyloxy)-6-((triMethylsilyloxy)Methyl)tetrahydro-2H-pyran-2-one,95%
  • 2,3,4,6- tetra -O- trimethylsilyl -D- gluconolactone
  • D-Gluconic acid, 2,3,4,6-tetrakis-O-(trimethylsilyl)-, δ-lactone
  • (3R,4S,5R,6R)-3,4,5-tris(TMS-oxy)-6-[(TMS-oxy)methyl]tetrahydro-2H-pyran-2-one/D-Gluconic acid, 2,3,4,6-tetrakis-O-(trimethylsilyl)-, δ-lactone
  • 2,3,4,6-tetra-O-Trimethylsilyl-beta-D-glucolactone
  • Canagliflozin Impurity 9(Dagelin impurity 11)
  • 2,3,4,6-tetra-O-trimethylsilyl-β-d- gluconolactone
  • (3R,4S,5R,6R)-3,4,5- Tri[(trimethylsilyl)oxy]-6- [[(Trimethylsilyl)oxy] methyl]tetrahydro-2H-pyran- 2-one
  • 2,3,4,6-tetra-O-Trimethyl silyl-beta-D-glucolacto Commercial
  • 2,3,4,6-tetrakis-O-(trimethylsilyl)-D-glocono-1,5-Lactone
  • (2R,3R,6S)-2-(acetoxymethyl)-6-(3-((5-(4-fluorophenyl)thiophen-2-yl)methyl)-2-methylphenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate
  • (3R,4S,5R,6R)-3,4,5-tris[(trimethylsilanyl)oxy]-6-{[(trimethylsilanyl)oxy]methyl}tetrahydro-2H-pyran-2-one
  • 32384-65-9
  • 32384-69-5
  • C18H42O6Si4