2,3,4,6-Tetra-O-acetyl-b-D-glucopyranosyl trichloroacetimidate

Base Information

• Chemical Name: 2,3,4,6-Tetra-O-acetyl-b-D-glucopyranosyl trichloroacetimidate
• CAS No.: 92052-29-4
• Molecular Formula: C16H20Cl3NO10
• Molecular Weight: 492.695
• Hs Code.: 2940000080
• DSSTox Substance ID: DTXSID00452848
• Nikkaji Number: J1.141.039A
• Wikidata: Q82273705
• Mol file: 92052-29-4.mol

Synonyms:92052-29-4;2,3,4,6-Tetra-O-acetyl-b-D-glucopyranosyl trichloroacetimidate;2,3,4,6-Tetra-O-acetyl-beta-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;SCHEMBL1726948;DTXSID00452848;AMY41454;AKOS016844828;CS-W006443;AS-72793;A860167;W-204069;2,3,4,6-Tetra-O-acetyl-b-D-glucopyranosyltrichloroacetimidate;1-O-(1-Imino-2,2,2-trichloroethyl)-beta-D-glucopyranose tetraacetate;2,3,4,6-Tetra-O-acetyl-1-O-(2,2,2-trichloroethanimidoyl)-beta-D-glucopyranose;[(2R,3R,4S,5R,6S)-3,4,5-TRIS(ACETYLOXY)-6-[(2,2,2-TRICHLOROETHANIMIDOYL)OXY]OXAN-2-YL]METHYL ACETATE

Chemical Property of 2,3,4,6-Tetra-O-acetyl-b-D-glucopyranosyl trichloroacetimidate

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 154.0 to 160.0 °C
• Boiling Point: 463.341°C at 760 mmHg
• PKA: 1.39±0.70(Predicted)
• Flash Point: 234.02°C
• PSA: 147.51000
• Density: 1.558g/cm³
• LogP: 1.53330
• Storage Temp.: Sealed in dry,Store in freezer, under -20°C
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 11
• Exact Mass: 491.015279
• Heavy Atom Count: 30
• Complexity: 695

Purity/Quality:

98%, ^*data from raw suppliers

2,3,4,6-Tetra-O-acetyl-b-D-glucopyranosyl trichloroacetimidate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OCC1C(C(C(C(O1)OC(=N)C(Cl)(Cl)Cl)OC(=O)C)OC(=O)C)OC(=O)C
• Isomeric SMILES: CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)OC(=N)C(Cl)(Cl)Cl)OC(=O)C)OC(=O)C)OC(=O)C

Technology Process of 2,3,4,6-Tetra-O-acetyl-b-D-glucopyranosyl trichloroacetimidate

There total 43 articles about 2,3,4,6-Tetra-O-acetyl-b-D-glucopyranosyl trichloroacetimidate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

2,3,4,6-tetra-O-acetyl-α/β-D-galactopyranose (3947-62-4,6207-76-7,10343-06-3,19235-21-3,22554-70-7,22860-22-6,57884-82-9,62057-79-8,70191-05-8,109525-54-4,140147-37-1,47339-09-3) + trichloroacetonitrile (545-06-2) → 2,3,4,6-tetra-O-acetyl-D-galactopyranosyl trichloroacetimidate (74808-10-9,86520-63-0,87119-53-7,92052-29-4,121238-27-5,142831-80-9,127061-80-7)

Guidance literature:

With potassium carbonate; In dichloromethane; at 20 ℃; for 16h; Inert atmosphere;

DOI:10.1039/c7ob01388d

Reference yield: 96.0%

D-galactose pentaacetate (25878-60-8) + trichloroacetonitrile (545-06-2) → 2,3,4,6-tetra-O-acetyl-D-galactopyranosyl trichloroacetimidate (74808-10-9,86520-63-0,87119-53-7,92052-29-4,121238-27-5,142831-80-9,127061-80-7)

Guidance literature:

D-galactose pentaacetate; With benzylamine; In N,N-dimethyl-formamide; at 20 ℃;

trichloroacetonitrile; With potassium carbonate; In dichloromethane;

DOI:10.1021/acs.bioconjchem.8b00902

Reference yield: 95.0%

2,3,4,6-tetra-O-acetyl-β-D-galactopyranose (70191-05-8) + trichloroacetonitrile (545-06-2) → 2,3,4,6-tetra-O-acetyl-D-galactopyranosyl trichloroacetimidate (74808-10-9,86520-63-0,87119-53-7,92052-29-4,121238-27-5,142831-80-9,127061-80-7)

Guidance literature:

With caesium carbonate; In dichloromethane; at 20 ℃;

DOI:10.1016/S0957-4166(02)00480-9

upstream raw materials:

2,3,4,5-tetra-O-acetyl-D-glucopyranose

trichloroacetonitrile

β-D-glucose pentaacetate

α-D-glucopyranose peracetylate

Downstream raw materials:

4′-methylumbelliferyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside

4-methylumbelliferyl β-D-glucopyranoside

(3R,4S,6R)-2-(acetoxymethyl)-6-(3-(5-(2-(benzyloxy)-2-oxoethyl)-3-tert-butyl-2,4-dioxoimidazolidin-1-yl)propoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate

(3R,4S,6R)-2-(acetoxymethyl)-6-(3-(5-(2-((S)-1-(benzyloxy)-4-methyl-1-oxopentan-2-ylamino)-2-oxoethyl)-3-tert-butyl-2,4-dioxoimidazolidin-1-yl)propoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate