ChemicalBook > CAS DataBase List > 2,3,4-Tri-O-acetyl-α-D-glucuronide methyl ester trichloroacetimidate

2,3,4-Tri-O-acetyl-α-D-glucuronide methyl ester trichloroacetimidate

Product Name
2,3,4-Tri-O-acetyl-α-D-glucuronide methyl ester trichloroacetimidate
CAS No.
92420-89-8
Chemical Name
2,3,4-Tri-O-acetyl-α-D-glucuronide methyl ester trichloroacetimidate
Synonyms
3,4, 6-tri-acetyl-alpha-D-glucopyrane 1,2-(methyl orthoacid);3,4,6-TRI-O-ACETYL-ALPHA-D-GLUCOPYRANOSE 1,2-(METHYL ORTHOACETATE);2,3,4-Tri-O-acetyl-a-D-glucuronide methyl ester trichloroacetimidate;2,3,4-Tri-O-acetyl-α-D-glucuronide methyl ester trichloroacetimidate;Methyl2,3,4-tri-O-acetyl-a-D-glucopyranosyluronosyltrichloroacetimidate;2,3,4-Tri-O-acetyl-Alpha-D-Glucuronide methyl ester trichloroacetimidate;2,3,4-Tri-O-acetyl-α-D-glucuronic Acid Methyl Ester Trichloroacetimidate;2,3,4-Tri-O-acetyl-α-D-glucu- ronide methyl ester trichloroace- timidate;2,3,4-Tri-O-acetyl-α-D-glucuronic Acid Methyl Ester, Trichloroacetimidate;Methyl-(2,3,4-tri-O-acetyl-α-D-glucopyranosyl Trichloroacetimidate)uronate
CBNumber
CB61092927
Molecular Formula
C15H18Cl3NO10
Formula Weight
478.66
MOL File
92420-89-8.mol
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2,3,4-Tri-O-acetyl-α-D-glucuronide methyl ester trichloroacetimidate Property

Melting point:
103-105°C
Boiling point:
442.1±55.0 °C(Predicted)
Density 
1.59±0.1 g/cm3(Predicted)
storage temp. 
Inert atmosphere,Store in freezer, under -20°C
solubility 
Chloroform (Slightly), Ethyl Acetate (Slightly)
form 
Solid
pka
1.39±0.70(Predicted)
color 
White to Light Brown
Stability:
Acid Sensitive, Temperature Sensitive
InChI
InChI=1/C15H18Cl3NO10/c1-5(20)25-8-9(26-6(2)21)11(27-7(3)22)13(28-10(8)12(23)24-4)29-14(19)15(16,17)18/h8-11,13,19H,1-4H3/t8-,9-,10-,11+,13+/s3
InChIKey
KWNIVSQDHXVNAL-HDOZVNRQNA-N
SMILES
[C@H]1(OC(=O)C)[C@H](OC(=O)C)[C@H](O[C@H](OC(=N)C(Cl)(Cl)Cl)[C@@H]1OC(=O)C)C(=O)OC |&1:0,5,10,12,20,r|
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Safety

HS Code 
2932990090
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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.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Usbiological
Product number
294751
Product name
2,3,4-Tri-O-acetyl-a-D-glucuronide methyl ester trichloroacetimidate
Packaging
50mg
Price
$368
Updated
2021/12/16
TRC
Product number
T765200
Product name
2,3,4-Tri-O-acetyl-α-D-glucuronicAcidMethylEsterTrichloroacetimidate
Packaging
1g
Price
$480
Updated
2021/12/16
Ark Pharm
Product number
P000075385
Product name
(2S,3S,4S,5R,6R)-2-(Methoxycarbonyl)-6-(2,2,2-trichloro-1-iminoethoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate
Purity
95+%
Packaging
5g
Price
$354
Updated
2021/12/16
AK Scientific
Product number
AG1039
Product name
2,3,4-Tri-O-acetyl-a-D-glucuronidemethylestertrichloroacetimidate
Packaging
1g
Price
$550
Updated
2021/12/16
Biosynth Carbosynth
Product number
MT04878
Product name
2,3,4-Tri-O-acetyl-a-D-glucuronide methyl ester trichloroacetimidate
Packaging
2g
Price
$600
Updated
2021/12/16
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2,3,4-Tri-O-acetyl-α-D-glucuronide methyl ester trichloroacetimidate Chemical Properties,Usage,Production

Chemical Properties

White Solid

Uses

Intermediate for the synthesis of various glucuronide derivatives

Synthesis

72692-06-9

545-06-2

92420-89-8

The general procedure for the synthesis of 3,4,6-tri-octa-acetyl-ALPHA-D-glucopyranose 1,2-(methyl orthoacetate) from (2S,3R,4S,5S,6S)-2-hydroxy-6-(methoxycarbonyl)tetrahydro-2H-pyran-3,4,5-triethyl triacetate and trichloroacetonitrile was performed as follows: 2,3,4-triacetyl-α,β-pyran methyl gluconate (12.0 g, 36 mmol) and trichloroacetonitrile (18 mL, 180 mmol) were dissolved in anhydrous CH2Cl2 and stirred for 30 min. Subsequently, DBU (1.5 mL, 10 mmol) was slowly added dropwise, and the reaction mixture was gradually warmed up to room temperature and continuously stirred overnight. Upon completion of the reaction, the solvent was removed by distillation under reduced pressure and the resulting residue was purified by fast column chromatography (eluent ratio 40:59:1 EtOAc-hexane-Et3N). The fraction containing the target product was collected and concentrated under reduced pressure to give a slurry, which was ground with ether. Further recrystallization with EtOAc-hexane (50:50) mixed solvent resulted in 8.5 g (65% yield) of off-white solid product. The melting point of the compound was 108-109 °C and literature reported values of 109-110 °C. Infrared spectroscopy (KBr) showed characteristic absorption peaks: v 3320 (N-H stretching vibration), 2958 (C-H stretching vibration), 1755 (C=O stretching vibration) cm-1. 1H NMR (CDCl3) data were as follows: δ 8.73 (s, 1H, NH), 6.64 (d, 1H, J=3.6 Hz, H-1), 5.63 (t, 1H, J =10Hz, H-3), 5.27 (t, 1H, J=10Hz, H-4), 5.16 (dd, 1H, J=3.6Hz, 10Hz, H-2), 4.49 (d, 1H, J=10Hz, H-5), 3.75 (s, 3H, CO2Me), 2.05 (s, 3H, OAc), 2.04 (s, 3H, OAc) , 2.02 (s, 3H, OAc). 13C NMR (CDCl3) data are as follows: δ 169.78 (CO), 169.72 (CO), 169.47 (CO), 167.14 (CO), 160.58 (CN), 92.64 (CH), 70.49 (CH), 69.47 (CH), 69.10 (CH). 68.96 (CH), 53.04 (CO2Me), 21.04,20.66,20.48,20.39 (3 × OAc and 1 × CCl3).

References

[1] Carbohydrate Research, 2003, vol. 338, # 22, p. 2337 - 2340
[2] MedChemComm, 2014, vol. 5, # 7, p. 984 - 988
[3] Journal of Chemical Research - Part S, 1997, # 10, p. 370 - 371
[4] Carbohydrate Research, 2012, vol. 349, p. 108 - 112
[5] Journal of Chemical Crystallography, 2013, vol. 43, # 3, p. 138 - 143

2,3,4-Tri-O-acetyl-α-D-glucuronide methyl ester trichloroacetimidate Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from 2,3,4-Tri-O-acetyl-α-D-glucuronide methyl ester trichloroacetimidate manufacturers

WUHAN FORTUNA CHEMICAL CO., LTD
Product
2,3,4-Tri-O-acetyl-α-D-glucuronide methyl ester trichloroacetimidate 92420-89-8
Price
US $0.00/G
Min. Order
1G
Purity
98%min
Supply Ability
30kg/month
Release date
2023-02-17
Jiangsu Nata Opto-electronic Material Co.,Ltd.
Product
2,3,4-Tri-O-acetyl-α-D-glucuronide methyl ester trichloroacetimidate 92420-89-8
Price
US $0.00-0.00/g
Min. Order
100g
Purity
98%
Supply Ability
10kg
Release date
2023-05-25
GlycoPharm.LLC
Product
2,3,4-Tri-O-acetyl-α-D-glucuronide methyl ester trichloroacetimidate 92420-89-8
Price
US $0.00/g/bag
Min. Order
25g/bag
Purity
97%HPLC
Supply Ability
MG-KG
Release date
2020-03-16

92420-89-8, 2,3,4-Tri-O-acetyl-α-D-glucuronide methyl ester trichloroacetimidateRelated Search:

1,3,4,6-Tetra-O-acetyl-2-deoxy-2-[(2-azidoacetyl)amino]-β-D-glucopyranose 4-NITROPHENYL-BETA-D-GLUCOPYRANOSIDE 2-Acetamido-2-deoxy-1,3,4,6-tetra-0-acetyl-alpha-D-glucopyranose n-Dodecyl-beta-D-maltoside 4-NITROPHENYL-ALPHA-D-GLUCOPYRANOSIDE N-DECYL-BETA-D-GLUCOPYRANOSIDE n-Octyl-β-D-glucopyranoside METHYL BETA-D-GLUCOPYRANOSIDE BETA-D-GLUCOSAMINE PENTAACETATE N-NONYL-BETA-D-GLUCOPYRANOSIDE METHYL 2,2,2-TRICHLOROACETIMIDATE 2,3,4-Tri-O-acetyl-α-D-glucuronide methyl ester trichloroacetimidate 2,3,4-Tri-O-acetyl-alpha-D-glucuronicacidmethylester 2-(2-CHLOROETHOXY)TETRAHYDRO-2H-PYRAN Methyl 2,3,4-Tri-O-isobutyryl-1-O-trichloroacetimidoyl-a-D-glucopyranuronate 2,3,4-Tri-O-benzoyl-alpha-D-glucopyranuronic acid methyl ester trichloroacetimidate 2,3,4-Tri-O-acetyl-beta-D-xylopyranosyl trichloroacetimidate ETHYL 2,2,2-TRICHLOROACETIMIDATE

  • 3,4,6-TRI-O-ACETYL-ALPHA-D-GLUCOPYRANOSE 1,2-(METHYL ORTHOACETATE)
  • Methyl2,3,4-tri-O-acetyl-a-D-glucopyranosyluronosyltrichloroacetimidate
  • 2,3,4-Tri-O-acetyl-α-D-glucuronic Acid Methyl Ester, Trichloroacetimidate
  • Methyl-(2,3,4-tri-O-acetyl-α-D-glucopyranosyl Trichloroacetimidate)uronate
  • 2,3,4-Tri-O-acetyl-a-D-glucuronide methyl ester trichloroacetimidate
  • Methyl 2,3,4-tri-O-acetyl-1-O-trichloroacetimidoyl-alpha-D-glucopyranosyluronate min. 99%
  • 2,3,4-tri-O-acetyl-1-(2,2,2-trichloroethanimidate)-α-D-glucopyranuronic acid methyl ester
  • (2S,3S,4S,5R,6R)-2-(Methoxycarbonyl)-6-(2,2,2-trichloro-1-iminoethoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate
  • 2,3,4-Tri-O-acetyl-Alpha-D-Glucuronide methyl ester trichloroacetimidate
  • O-(2,3,4-Tri-O-acetyl-α-D-glucuronic acid methyl ester) trichloroacetimidate
  • "METHYL 3 4 5-TRIS(ACETYLOXY)-6-[(TRICHLOROETHANIMIDOYL)OXY]OXANE-2-CARBOXYLATE
  • 2,3,4-Tri-O-acetyl-α-D-glucuronide methyl ester trichloroacetimidate
  • 2,3,4-Tri-O-acetyl-1-O-trichloroacetimidoyl-α-D-glucopyranuronic acid methyl ester
  • α-D-Glucopyranuronic acid, methyl ester, 2,3,4-triacetate 1-(2,2,2-trichloroethanimidate)
  • 2,3,4-Tri-O-acetyl-α-D-glucuronic Acid Methyl Ester Trichloroacetimidate
  • 3,4, 6-tri-acetyl-alpha-D-glucopyrane 1,2-(methyl orthoacid)
  • 2,3,4-Tri-O-acetyl-α-D-glucu- ronide methyl ester trichloroace- timidate
  • 2,3,4-Tri-O-acetyl-α-D-glucopyranuronic acid methyl ester trichloroacetimidate
  • Methyl 2,3,4-tri-O-acetyl-1-O-trichloroacetimidoyl-alpha-D-glucopyranosyluronate
  • 92420-89-8
  • 13C & 2H Sugars
  • Carbohydrates & Derivatives
  • Intermediates