Methyl 4-Azido-4,6-dideoxy-2-O-methyl-3-O-benzyl-α-D-glucopyranoside

Base Information

• Chemical Name: Methyl 4-Azido-4,6-dideoxy-2-O-methyl-3-O-benzyl-α-D-glucopyranoside
• CAS No.: 861819-28-5
• Molecular Formula: C15H21 N3 O4
• Molecular Weight: 307.34494
• Mol file: 861819-28-5.mol

Synonyms:Methyl 4-Azido-4,6-dideoxy-2-O-methyl-3-O-(phenylmethyl)-α-D-glucopyranoside;Methyl 4-Azido-4,6-dideoxy-2-O-methyl-3-O-benzyl-α-D-glucopyranoside;Methyl 4-Azido-4,6-dideoxy-2-O-methyl-3-O-(phenylmethyl)-a-D-glucopyranoside;Methyl 4-Azido-4,6-dideoxy-2-O-methyl-3-O-benzyl-a-D-glucopyranoside

Chemical Property of Methyl 4-Azido-4,6-dideoxy-2-O-methyl-3-O-benzyl-α-D-glucopyranoside

Chemical Property:

• PSA: 86.67000
• LogP: 2.10966
• Solubility.: Dichloromethane, Ethyl Acetate, Methanol

Purity/Quality:

98% ^*data from raw suppliers

Methyl 4-azido-3-O-benzyl-4,6-dideoxy-2-O-methyl-a-D-glucopyranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Methyl 4-Azido-4,6-dideoxy-2-O-methyl-3-O-benzyl-α-D-glucopyranoside (cas# 861819-28-5) is a compound useful in organic synthesis.

Technology Process of Methyl 4-Azido-4,6-dideoxy-2-O-methyl-3-O-benzyl-α-D-glucopyranoside

There total 8 articles about Methyl 4-Azido-4,6-dideoxy-2-O-methyl-3-O-benzyl-α-D-glucopyranoside 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%

methyl 4-azido-4,6-dideoxy-2-O-methyl-α-D-glucopyranoside (1314865-01-4) + benzyl bromide (100-39-0) → methyl 4-azido-3-O-benzyl-4,6-dideoxy-2-O-methyl-α-D-glucopyranoside (861819-28-5)

Guidance literature:

methyl 4-azido-4,6-dideoxy-2-O-methyl-α-D-glucopyranoside; With sodium hydride; In tetrahydrofuran; mineral oil; at 0 ℃; for 0.166667h; Inert atmosphere;

benzyl bromide; In tetrahydrofuran; mineral oil; at 20 ℃;

DOI:10.1021/jo200340q

Reference yield: 87.0%

methyl 4-azido-3-O-benzyl-4,6-dideoxy-α-D-glucopyranoside (861819-27-4) + methyl iodide (74-88-4) → methyl 4-azido-3-O-benzyl-4,6-dideoxy-2-O-methyl-α-D-glucopyranoside (861819-28-5)

Guidance literature:

With dimethylsulfide; silver(l) oxide; In 1,2-dimethoxyethane; at 20 ℃;

DOI:10.1016/j.carres.2005.04.010

Reference yield:

methyl 4-azido-3-O-benzyl-4,6-dideoxy-2-O-trifluoromethanesulfonyl-α-D-mannopyranoside (861819-26-3) → methyl 4-azido-3-O-benzyl-4,6-dideoxy-2-O-methyl-α-D-glucopyranoside (861819-28-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 54.7 percent / NaNO₂ / dimethylformamide / 8 h / 80 °C

2: 87 percent / Ag₂O; Me₂S / 1,2-dimethoxy-ethane / 20 °C

With dimethylsulfide; silver(l) oxide; sodium nitrite; In 1,2-dimethoxyethane; N,N-dimethyl-formamide;

DOI:10.1016/j.carres.2005.04.010

upstream raw materials:

methyl 4-azido-3-O-benzyl-4,6-dideoxy-α-D-glucopyranoside

methyl iodide

methyl 4-azido-3-O-benzyl-4,6-dideoxy-2-O-trifluoromethanesulfonyl-α-D-mannopyranoside

methyl 4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranoside

Downstream raw materials:

1-acetyl-4-azido-3-O-benzyl-4,6-dideoxy-2-O-methyl-D-glucopyranose

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