1,3,4,6-Tetra-O-acetyl-2-chloroacetamido-2-deoxy-beta-glucopyranose

Base Information

• Chemical Name: 1,3,4,6-Tetra-O-acetyl-2-chloroacetamido-2-deoxy-beta-glucopyranose
• CAS No.: 68499-56-9
• Molecular Formula: C16H22ClNO10
• Molecular Weight: 423.804
• DSSTox Substance ID: DTXSID20988154
• Nikkaji Number: J75.621K
• Wikidata: Q82976612
• ChEMBL ID: CHEMBL3246469
• Mol file: 68499-56-9.mol

Synonyms:1,3,4,6-tetra-O-acetyl-2-chloroacetamido-2-deoxy-beta-glucopyranose;TCDG

Chemical Property of 1,3,4,6-Tetra-O-acetyl-2-chloroacetamido-2-deoxy-beta-glucopyranose

Chemical Property:

• Vapor Pressure: 2.58E-12mmHg at 25°C
• Boiling Point: 554°Cat760mmHg
• Flash Point: 288.9°C
• PSA: 143.53000
• Density: 1.36g/cm³
• LogP: -0.18460
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 11
• Exact Mass: 423.0932236
• Heavy Atom Count: 28
• Complexity: 625

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of 1,3,4,6-Tetra-O-acetyl-2-chloroacetamido-2-deoxy-beta-glucopyranose

There total 11 articles about 1,3,4,6-Tetra-O-acetyl-2-chloroacetamido-2-deoxy-beta-glucopyranose 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: 91.0%

chloroacetyl chloride (79-04-9) + tetra-acetyl glucosamine (17460-45-6,23707-23-5,23739-93-7,23743-51-3,26108-75-8,59042-16-9,124516-07-0,124580-56-9) → 1,3,4,6-tetra-O-acetyl-2-chloroacetamido-2-deoxy-β-D-glucopyranoside (68499-56-9)

Guidance literature:

With 2,6-dimethylpyridine; In chloroform; at -10 - 0 ℃; for 1h;

DOI:10.1016/0008-6215(85)85205-8

Reference yield: 90.0%

1,3,4,6-tetra-O-acetyl-D-glucosamine hydrochloride (5432-46-2,10034-19-2,10034-20-5,34948-62-4,110253-00-4,1191127-63-5) + Chloroacetic anhydride (541-88-8) → 1,3,4,6-tetra-O-acetyl-2-chloroacetamido-2-deoxy-β-D-glucopyranoside (68499-56-9)

Guidance literature:

With triethylamine; In dichloromethane; at 20 ℃; for 3.67h; Cooling with ice;

DOI:10.1039/c9cc02051a

Reference yield: 72.0%

1,3,4,6-tetra-O-acetyl-D-glucosamine hydrochloride (5432-46-2,10034-19-2,10034-20-5,34948-62-4,110253-00-4,1191127-63-5) + chloroacetyl chloride (79-04-9) → 1,3,4,6-tetra-O-acetyl-2-chloroacetamido-2-deoxy-β-D-glucopyranoside (68499-56-9)

Guidance literature:

With triethylamine; In dichloromethane;

DOI:10.1016/0008-6215(90)84083-7

upstream raw materials:

tetra-acetyl glucosamine

1,3,4,6-tetra-O-acetyl-D-glucosamine hydrochloride

chloroacetyl chloride

Chloroacetic anhydride

Downstream raw materials:

allyl O-(3,4,6-tri-O-acetyl-2-chloroacetamido-2-deoxy-β-D-glucopyranosyl)-(1->4)-2,4,6-tri-O-benzyl-α-D-galactopyranoside

allyl 3,4,6-tri-O-acetyl-2-(chloroacetamido)-2-deoxy-β-D-glucopyranoside

allyl O-(3,4,6-tri-O-acetyl-2-chloroacetamido-2-deoxy-α-D-glucopyranosyl)-(1->4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside

allyl O-(3,4,6-tri-O-acetyl-2-chloroacetamido-2-deoxy-β-D-glucopyranosyl)-(1->4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside