Methyl2-azido-2-deoxy-3-O-(phenylmethyl)-alpha-D-glucopyranoside6-benzoate

Base Information

• Chemical Name: Methyl2-azido-2-deoxy-3-O-(phenylmethyl)-alpha-D-glucopyranoside6-benzoate
• CAS No.: 501088-17-1
• Molecular Formula: C21H23N3O6
• Molecular Weight: 413.43
• Mol file: 501088-17-1.mol

Synonyms:Methyl2-azido-2-deoxy-3-O-(phenylMethyl)-alpha-D-glucopyranoside6-benzoate;METHYL 2-AZIDO-2-DEOXY-3-O-BENZYL-6-O-BENZOYL-A-D-GLUCOPYRANOSIDE;

Chemical Property of Methyl2-azido-2-deoxy-3-O-(phenylmethyl)-alpha-D-glucopyranoside6-benzoate

Chemical Property:

• PSA: 123.97000
• LogP: 2.29266

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Methyl2-azido-2-deoxy-3-O-(phenylmethyl)-alpha-D-glucopyranoside6-benzoate

There total 35 articles about Methyl2-azido-2-deoxy-3-O-(phenylmethyl)-alpha-D-glucopyranoside6-benzoate 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: 96.0%

benzoyl chloride (98-88-4) + methyl 2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranoside (175978-55-9) → methyl 2-azido-6-O-benzoyl-3-O-benzyl-2-deoxy-α-D-glucopyranoside (501088-17-1)

Guidance literature:

In pyridine; dichloromethane; at 0 ℃; for 0.5h;

DOI:10.1016/j.carres.2006.02.020

Reference yield: 89.0%

methyl 2-azido-6-O-benzoyl-3-O-benzyl-2-deoxy-4-O-(2-naphthylmethyl)-α-D-glucopyranoside (1355357-15-1) → methyl 2-azido-6-O-benzoyl-3-O-benzyl-2-deoxy-α-D-glucopyranoside (501088-17-1)

Guidance literature:

With water; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; for 5h;

DOI:10.1039/c1ob06415k

Reference yield:

Methyl 2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside (162678-87-7) → methyl 2-azido-6-O-benzoyl-3-O-benzyl-2-deoxy-α-D-glucopyranoside (501088-17-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 71 percent / HOAc / H₂O / 70 °C

2: 96 percent / CH₂Cl₂; pyridine / 0.5 h / 0 °C

With acetic acid; In pyridine; dichloromethane; water;

DOI:10.1016/j.carres.2006.02.020

upstream raw materials:

benzoyl chloride

methyl 2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranoside

methyl 2-azido-2-deoxy-α/β-D-glucopyranoside

(+)-D-glucosamine hydrochloride

Downstream raw materials:

methyl O-(methyl 2-O-benzoyl-3-O-benzyl-4-O-(4-(((9H-fluoren-9-yl)methoxy)carbonyloxy)-α-L-idopyranosyluronate)-(1→4)-2-azido-6-O-benzoyl-3-benzyl-2-deoxy-α-D-glucopyranoside)

Refernces

• 1、 -. "METHOD FOR PREPARING FULLY PROTECTION HEPARIN PENTASACCHARIDE AND INTERMEDIATE THEREOF". Paragraph 0038; 0052; 0093-0095. . Retrieved 2015/04/15.
• 2、 -. "AN EFFICIENT AND SCALABLE PROCESS FOR THE MANUFACTURE OF FONDAPARINUX SODIUM". Page/Page column 23; 37; 59. . Retrieved 2013/08/15.