methyl 2-azido-2-deoxy-3,4-di-O-(benzyl)-α-D-glucopyranoside

Base Information

• Chemical Name: methyl 2-azido-2-deoxy-3,4-di-O-(benzyl)-α-D-glucopyranoside
• CAS No.: 352547-12-7
• Molecular Formula: C₂₁H₂₅N₃O₅
• Molecular Weight: 399.447
• Mol file: 352547-12-7.mol

Synonyms:methyl 2-azido-2-deoxy-3,4-di-O-(benzyl)-α-D-glucopyranoside

Chemical Property of methyl 2-azido-2-deoxy-3,4-di-O-(benzyl)-α-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 2-azido-2-deoxy-3,4-di-O-(benzyl)-α-D-glucopyranoside

There total 4 articles about methyl 2-azido-2-deoxy-3,4-di-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: 86.0%

Methyl 2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside (162678-87-7) → methyl 2-azido-2-deoxy-3,4-di-O-(benzyl)-α-D-glucopyranoside (352547-12-7)

Guidance literature:

With borane-THF; copper(II) bis(trifluoromethanesulfonate); In tetrahydrofuran; for 14h; cooling;

DOI:10.1002/anie.200462172

Reference yield:

C37H43N3O5Si → methyl 2-azido-2-deoxy-3,4-di-O-(benzyl)-α-D-glucopyranoside (352547-12-7)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 50 ℃; for 18h;

DOI:10.1021/acs.inorgchem.8b03035

Reference yield:

methyl 2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranoside (175978-55-9) → methyl 2-azido-2-deoxy-3,4-di-O-(benzyl)-α-D-glucopyranoside (352547-12-7)

Guidance literature:

Multi-step reaction with 3 steps

1: triethylamine; dmap / N,N-dimethyl-formamide / 15 h / 20 °C

2: sodium hydride / N,N-dimethyl-formamide; mineral oil / 6 h / 0 - 20 °C

3: tetrabutyl ammonium fluoride / tetrahydrofuran / 18 h / 50 °C

With dmap; tetrabutyl ammonium fluoride; sodium hydride; triethylamine; In tetrahydrofuran; N,N-dimethyl-formamide; mineral oil;

DOI:10.1021/acs.inorgchem.8b03035

upstream raw materials:

Methyl 2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside

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

C₃₀H₃₇N₃O₅Si

Downstream raw materials:

C₆₂H₆₈N₄O₂₆