phenyl 2-azido-3,6-di-O-benzyl-2-deoxy-1-thio-β-D-glucopyranoside

Base Information

• Chemical Name: phenyl 2-azido-3,6-di-O-benzyl-2-deoxy-1-thio-β-D-glucopyranoside
• CAS No.: 277756-87-3
• Molecular Formula: C₂₆H₂₇N₃O₄S
• Molecular Weight: 477.584
• Mol file: 277756-87-3.mol

Synonyms:phenyl 2-azido-3,6-di-O-benzyl-2-deoxy-1-thio-β-D-glucopyranoside

Chemical Property of phenyl 2-azido-3,6-di-O-benzyl-2-deoxy-1-thio-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

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Technology Process of phenyl 2-azido-3,6-di-O-benzyl-2-deoxy-1-thio-β-D-glucopyranoside

There total 17 articles about phenyl 2-azido-3,6-di-O-benzyl-2-deoxy-1-thio-β-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%

phenyl 2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-1-thio-β-D-glucopyranoside (277756-86-2) → phenyl 2-azido-3,6-di-O-benzyl-2-deoxy-1-thio-β-D-glucopyranoside (277756-87-3)

Guidance literature:

With MS 3 Angstroem; sodium cyanoborohydride; In tetrahydrofuran; at 25 ℃; for 0.5h;

DOI:10.1002/(SICI)1099-0690(200004)2000:8<1547::AID-EJOC1547<3.0.CO;2-C

Reference yield: 84.0%

phenyl 2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-1-thio-β-D-glucopyranoside (277756-86-2) → phenyl 2-azido-3,6-di-O-benzyl-2-deoxy-1-thio-β-D-glucopyranoside (277756-87-3) + phenyl 2-azido-3-O-benzyl-2-deoxy-1-thio-β-D-glucopyranoside (666753-83-9)

Guidance literature:

With triethylsilane; boron trifluoride diethyl etherate; In dichloromethane; at 0 ℃; for 4h; Inert atmosphere;

DOI:10.1021/jo300722y

Reference yield: 79.0%

phenyl 2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-1-thio-β-D-glucopyranoside → phenyl 2-azido-3,6-di-O-benzyl-2-deoxy-1-thio-β-D-glucopyranoside (277756-87-3)

Guidance literature:

With triethylsilane; boron trifluoride diethyl etherate; In dichloromethane; at 0 ℃; for 3h;

DOI:10.1021/jacs.1c00076

upstream raw materials:

phenyl 2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-1-thio-β-D-glucopyranoside

benzyl bromide

phenyl 2-azido-2-deoxy-1-thio-β-D-glucopyranoside

phenyl 2-azido-4,6-O-benzylidene-2-deoxy-1-thio-β-D-glucopyranoside

Downstream raw materials:

phenyl 2-azido-2-deoxy-3,6-di-O-benzyl-4-O-trichloroacetyl-1-thio-β-D-glucopyranoside