ChemicalBook > CAS DataBase List > 2,3,4,6-Tetra-O-acetyl-beta-D-glucopyranosyl 2,2,2-Trichloroacetimidate

2,3,4,6-Tetra-O-acetyl-beta-D-glucopyranosyl 2,2,2-Trichloroacetimidate

Product Name
2,3,4,6-Tetra-O-acetyl-beta-D-glucopyranosyl 2,2,2-Trichloroacetimidate
CAS No.
92052-29-4
Chemical Name
2,3,4,6-Tetra-O-acetyl-beta-D-glucopyranosyl 2,2,2-Trichloroacetimidate
Synonyms
[(2S,3R,4S,5S,6S)-3,4,5-triacetoxy-6-(2,2,2-trichloroethanimidoyl)oxy-tetrahydropyran-2-yl]methyl acetate;2,3,4,6-Tetra-O-acetyl-β-D-glucopyranosyl 2,2,2-Trichloroacetimidate;2,3,4,6-Tetra-O-acetyl-b-D-glucopyranosyl trichloroacetimidate;2,3,4,6-Tetra-O-acetyl-β-D-glucopyranosyl trichloroacetimidate;2,3,4,6-Tetra-O-acetyl-beta-D-glucopyranosyl trichloroacetimidate;2,3,4,6-Tetra-O-acetyl-1-O-trichloroacetimidoyl-β-D-glucopyranoside;2,3,4,6-Tetra-O-acetyl-β-D-glucopyranosyl 2,2,2-Trichloroacetimidate;2,3,4,6-Tetra-O-acetyl-β-D-glucopyranosyl trichloroacetimidate, 98%(N);2,3,4,6-Tetra-O-acetyl-β-D-galactopyranosyl 2,2,2-trichloroacetimidate
CBNumber
CB82129741
Molecular Formula
C16H20Cl3NO10
Formula Weight
492.69
MOL File
92052-29-4.mol
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2,3,4,6-Tetra-O-acetyl-beta-D-glucopyranosyl 2,2,2-Trichloroacetimidate Property

Melting point:
154.0 to 160.0 °C
Boiling point:
463.3±55.0 °C(Predicted)
Density 
1.55±0.1 g/cm3(Predicted)
storage temp. 
Sealed in dry,Store in freezer, under -20°C
form 
powder to crystal
pka
1.39±0.70(Predicted)
color 
White to Almost white
InChI
InChI=1/C16H20Cl3NO10/c1-6(21)25-5-10-11(26-7(2)22)12(27-8(3)23)13(28-9(4)24)14(29-10)30-15(20)16(17,18)19/h10-14,20H,5H2,1-4H3/t10-,11-,12+,13-,14+/s3
InChIKey
IBUZGVQIKARDAF-SZYILJKCNA-N
SMILES
C(Cl)(C(=N)O[C@@H]1O[C@@H]([C@H]([C@H](OC(C)=O)[C@H]1OC(=O)C)OC(C)=O)COC(C)=O)(Cl)Cl |&1:5,7,8,9,14,r|
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Safety

HS Code 
2940000080
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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

TCI Chemical
Product number
T2491
Product name
2,3,4,6-Tetra-O-acetyl-β-D-glucopyranosyl 2,2,2-Trichloroacetimidate
Purity
>98.0%(N)
Packaging
1g
Price
$98
Updated
2025/07/31
TCI Chemical
Product number
T2491
Product name
2,3,4,6-Tetra-O-acetyl-β-D-glucopyranosyl 2,2,2-Trichloroacetimidate
Purity
>98.0%(N)
Packaging
5g
Price
$294
Updated
2025/07/31
TRC
Product number
T283923
Product name
2,3,4,6-Tetra-O-acetyl-b-D-glucopyranosylTrichloroacetimidate
Packaging
50mg
Price
$60
Updated
2021/12/16
Usbiological
Product number
294964
Product name
2,3,4,6-Tetra-O-acetyl-b-D-glucopyranosyl trichloroacetimidate
Packaging
1g
Price
$496
Updated
2021/12/16
Chem-Impex
Product number
32298
Product name
2,3,4,6-Tetra-O-acetyl-β-D-glucopyranosyl2,2,2-trichloroacetimidate,98%(T)
Purity
98%(T)
Packaging
100MG
Price
$44.8
Updated
2021/12/16
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2,3,4,6-Tetra-O-acetyl-beta-D-glucopyranosyl 2,2,2-Trichloroacetimidate Chemical Properties,Usage,Production

Uses

2,3,4,6-Tetra-O-acetyl-β-D-glucopyranosyl trichloroacetimidate, 98%(N) (2,3,4,6-Tetra-O-acetyl-&beta) can be used in glycobiology research.

Synthesis

3947-62-4

545-06-2

74808-10-9

1. (2R,3R,4S,5R,6R)-2-(Acetoxymethyl)-6-hydroxytetrahydro-2H-pyran-3,4,5-triyl triacetate (5 g, 12.8 mmol) was dissolved in DMF (60 mL) and hydrazine acetate (1.3 g, 14.1 mmol) was added. The reaction mixture was stirred at room temperature overnight and subsequently concentrated to dryness under reduced pressure. The residue was dissolved with EtOAc (200 mL) and washed sequentially with saturated aqueous NaHCO3 and deionized water. The organic phase was dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. Purification by silica gel column chromatography (eluent: hexane-EtOAc, 1:1, v/v) afforded a white solid product (4.27 g, 96% yield). 2. The above product (2.1 g, 6.03 mmol), trichloroacetonitrile (12.1 mL, 121 mmol) and DCM (40 mL) were mixed and cooled to 0 °C. Cs2CO3 (1.96 g, 6.03 mmol) was added and stirred at room temperature for 1 hour. The reaction mixture was concentrated under reduced pressure and purified by silica gel column chromatography (eluent: hexane-EtOAc, 2:1, v/v) to give white solid sialyl ester (2.85 g, 96% yield). 3. The sialyl ester (0.88 g, 1.62 mmol), acceptor (0.73 g, 1.1 mmol), molecular sieve MS-4A and DCM (40 mL) were mixed and stirred at room temperature for 30 min. After cooling to -70 °C, TfOH (29 μL, 0.32 mmol) was added. The reaction mixture was stirred at -70 to -20 °C for 1 h and quenched with Et3N (0.05 mL). The mixture was diluted with DCM (200 mL), washed sequentially with saturated aqueous NaHCO3 and deionized water, the organic phase was dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. Purification by silica gel column chromatography (eluent: hexane-EtOAc, 3:2, v/v) gave a white solid disaccharide product (1.05 g, 95% yield). The 1H-NMR (500 MHz, CDCl3) and 13C-NMR (75 MHz, CDCl3) data were consistent with the structure of the target compound.

References

[1] Organic and Biomolecular Chemistry, 2017, vol. 15, # 26, p. 5602 - 5608
[2] Tetrahedron Letters, 2005, vol. 46, # 14, p. 2445 - 2448
[3] Patent: WO2012/135049, 2012, A1. Location in patent: Page/Page column 58-59
[4] Chemistry - An Asian Journal, 2014, vol. 9, # 7, p. 1786 - 1796
[5] Chinese Chemical Letters, 2016, vol. 27, # 12, p. 1740 - 1744

2,3,4,6-Tetra-O-acetyl-beta-D-glucopyranosyl 2,2,2-Trichloroacetimidate Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from 2,3,4,6-Tetra-O-acetyl-beta-D-glucopyranosyl 2,2,2-Trichloroacetimidate manufacturers

WUHAN FORTUNA CHEMICAL CO., LTD
Product
2,3,4,6-Tetra-O-acetyl-beta-D-glucopyranosyl 2,2,2-Trichloroacetimidate 92052-29-4
Price
US $0.00/G
Min. Order
1G
Purity
98%min
Supply Ability
30kg/month
Release date
2023-02-17
Career Henan Chemical Co
Product
2,3,4,6-Tetra-O-acetyl-beta-D-glucopyranosyl 2,2,2-Trichloroacetimidate 92052-29-4
Price
US $1.00/KG
Min. Order
1KG
Purity
97%-99.9%
Supply Ability
100kg
Release date
2019-12-20

92052-29-4, 2,3,4,6-Tetra-O-acetyl-beta-D-glucopyranosyl 2,2,2-TrichloroacetimidateRelated Search:

4-Methylumbelliferyl-beta-D-glucopyranoside Diosgenin-3-O-Β-D-glucuronide 2,3,4,6-TETRA-O-ACETYL-BETA-D-GLUCOPYRANOSE 2,3,4-Tri-O-acetyl-α-D-glucuronic Acid Methyl Ester Phenyl 2,3,4,6-Tetra-O-acetyl-1-thio-a-D-mannopyranoside 2-Phenylethyl-beta-D-thiogalactoside Ethyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-b-D-thioglucopyranoside 2-ACETAMIDO-2-DEOXY-ALPHA-D-GLUCOPYRANOSYL CHLORIDE 3,4,6-TRIACETATE α-D-Mannopyranosyl Fluoride 1-AZIDO-2,3,4,6-TETRA-O-ACETYL-BETA-D-GLUCOSE 2-O-Benzyl-1,3,4,6-tetra-O-acetyl-a-D-mannopyranose 2,3,4-Tri-O-acetyl-beta-D-xylopyranosyl trichloroacetimidate METHYL 2,2,2-TRICHLOROACETIMIDATE 2,3,4,6-Tetra-O-acetyl-beta-D-glucopyranosyl 2,2,2-Trichloroacetimidate

  • 2,3,4,6-Tetra-O-acetyl-beta-D-glucopyranosyl 2,2,2-Trichloroacetimidate
  • 2,3,4,6-Tetra-O-acetyl-b-D-glucopyranosyl trichloroacetimidate
  • 2,3,4,6-Tetra-O-acetyl-1-O-trichloroacetimidoyl-beta-D-glucopyranoside min. 99%
  • 2,3,4,6-Tetra-O-acetyl-beta-D-glucopyranosyl trichloroacetimidate
  • -<small>D</small>-glucopyranosyl 2,2,2-Trichloroacetimidate
  • 2,3,4,6-Tetra-<i>O</i>-acetyl-&beta
  • 2,3,4,6-Tetra-O-acetyl-1-O-trichloroacetimidoyl-β-D-glucopyranoside
  • 2,3,4,6-Tetra-O-acetyl-β-D-glucopyranosyl trichloroacetimidate
  • [(2S,3R,4S,5S,6S)-3,4,5-triacetoxy-6-(2,2,2-trichloroethanimidoyl)oxy-tetrahydropyran-2-yl]methyl acetate
  • 2,3,4,6-Tetra-O-acetyl-β-D-glucopyranosyl 2,2,2-Trichloroacetimidate
  • [(2R,3R,4S,5R,6S)-3,4,5-triacetyloxy-6-(2,2,2-trichloroethanimidoyl)oxyoxan-2-yl]methyl acetate
  • β-D-Glucopyranose, 2,3,4,6-tetraacetate 1-(2,2,2-trichloroethanimidate) (9CI, ACI)
  • β-D-Glucopyranose, 2,3,4,6-tetraacetate 1-(2,2,2-trichloroethanimidate)
  • 2,3,4,6-Tetra-O-acetyl-β-D-glucopyranosyl 2,2,2-Trichloroacetimidate, ≥ 98.0%
  • (2R,3R,4S,5R,6S)-3,4,5-tris(acetyloxy)-6-[(2,2,2-trichloroethanimidoyl)oxy]oxan-2-yl]methyl acetate
  • 2,3,4,6-Tetra-O-acetyl-β-D-glucopyranosyl trichloroacetimidate, 98%(N)
  • 2,3,4,6-Tetra-O-acetyl-beta-D-glucopyranosyl 2,2,2-Trichloroacetimidate，97%
  • 2,3,4,6-Tetra-O-acetyl-β-D-galactopyranosyl 2,2,2-trichloroacetimidate
  • 2,3,4,6-Tetra-O-acetyl-1-O-trichloroacetimidoyl-beta-D-glucopyranoside
  • 92052-29-4