methyl 4,6-di-O-benzyl-2,3-dideoxy-α-D-threo-hex-2-enopyranoside

Base Information

• Chemical Name: methyl 4,6-di-O-benzyl-2,3-dideoxy-α-D-threo-hex-2-enopyranoside
• CAS No.: 1053182-38-9
• Molecular Formula: C₂₁H₂₄O₄
• Molecular Weight: 340.419
• Mol file: 1053182-38-9.mol

Synonyms:methyl 4,6-di-O-benzyl-2,3-dideoxy-α-D-threo-hex-2-enopyranoside

Chemical Property of methyl 4,6-di-O-benzyl-2,3-dideoxy-α-D-threo-hex-2-enopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 4,6-di-O-benzyl-2,3-dideoxy-α-D-threo-hex-2-enopyranoside

There total 4 articles about methyl 4,6-di-O-benzyl-2,3-dideoxy-α-D-threo-hex-2-enopyranoside 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: 97.0%

methyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-threo-hex-2-enopyranoside (6605-29-4) + benzyl bromide (100-39-0) → methyl 4,6-di-O-benzyl-2,3-dideoxy-α-D-threo-hex-2-enopyranoside (1053182-38-9)

Guidance literature:

methyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-threo-hex-2-enopyranoside; With sodium methylate; In methanol; dichloromethane; at 20 ℃; for 2h;

benzyl bromide; With sodium hydride; In tetrahydrofuran; at 20 ℃; for 21h;

DOI:10.1021/acs.orglett.6b03000

Reference yield: 91.0%

methanol (67-56-1) + 4,6-di-O-benzyl-D-galactal (81928-98-5) → methyl 4,6-di-O-benzyl-2,3-dideoxy-α-D-threo-hex-2-enopyranoside (1053182-38-9)

Guidance literature:

With indium(III) chloride; In dichloromethane; at 30 ℃; for 26h; optical yield given as %de; Inert atmosphere;

DOI:10.1016/j.tetlet.2009.04.084

Reference yield:

methanol (67-56-1) + 4,6-di-O-benzyl-3-O-diethoxyphosphanyl-D-galactal → methyl 4,6-di-O-benzyl-2,3-dideoxy-α-D-threo-hex-2-enopyranoside (1053182-38-9) + methyl 2,3-Dideoxy-4,6-di-O-benzyl-β-D-threo-hex-2-enopyranoside

Guidance literature:

With aluminum (III) chloride; In dichloromethane; at 0 ℃; for 0.5h; stereoselective reaction; Inert atmosphere;

DOI:10.1016/j.tet.2014.11.027

upstream raw materials:

methanol

4,6-di-O-benzyl-D-galactal

methyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-threo-hex-2-enopyranoside

benzyl bromide