methyl 4,6-O-benzylidene-2,3-dideoxy-2-C-(2-hydroxyethyl)-3-C-((Z)-2-hydroxyethylidene)-α-D-ribo-hexopyranoside

Base Information

Chemical Name:methyl 4,6-O-benzylidene-2,3-dideoxy-2-C-(2-hydroxyethyl)-3-C-((Z)-2-hydroxyethylidene)-α-D-ribo-hexopyranoside
CAS No.:101199-50-2
Molecular Formula:C₁₈H₂₄O₆
Molecular Weight:336.385
Hs Code.:

Synonyms:methyl 4,6-O-benzylidene-2,3-dideoxy-2-C-(2-hydroxyethyl)-3-C-((Z)-2-hydroxyethylidene)-α-D-ribo-hexopyranoside

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Chemical Property of methyl 4,6-O-benzylidene-2,3-dideoxy-2-C-(2-hydroxyethyl)-3-C-((Z)-2-hydroxyethylidene)-α-D-ribo-hexopyranoside

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Technology Process of methyl 4,6-O-benzylidene-2,3-dideoxy-2-C-(2-hydroxyethyl)-3-C-((Z)-2-hydroxyethylidene)-α-D-ribo-hexopyranoside

There total 3 articles about methyl 4,6-O-benzylidene-2,3-dideoxy-2-C-(2-hydroxyethyl)-3-C-((Z)-2-hydroxyethylidene)-α-D-ribo-hexopyranoside 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: 71.0%

: 101199-49-9
methyl 4,6-O-benzylidene-2,3-dideoxy-2-C-((ethoxycarbonyl)methyl)-3-C-((Z)-(ethoxycarbonyl)methylene)-α-D-ribo-hexopyranoside

: 101199-50-2
methyl 4,6-O-benzylidene-2,3-dideoxy-2-C-(2-hydroxyethyl)-3-C-((Z)-2-hydroxyethylidene)-α-D-ribo-hexopyranoside

Guidance literature:: With diisobutylaluminium hydride; In dichloromethane;
DOI:10.1021/jo00283a033

Reference yield:

: 122672-65-5
methyl 2-deoxy-2-(2-ethoxy-2-oxoethyl)-4,6-O-(phenylmethylene)-α-D-ribohexopyranosid-3-ulose

: 101199-50-2
methyl 4,6-O-benzylidene-2,3-dideoxy-2-C-(2-hydroxyethyl)-3-C-((Z)-2-hydroxyethylidene)-α-D-ribo-hexopyranoside

Guidance literature:: Multi-step reaction with 2 steps

1: 98 percent / acetonitrile / 72 h / Heating

2: 71 percent / DIBAL / CH₂Cl₂

With diisobutylaluminium hydride; In dichloromethane; acetonitrile;
DOI:10.1021/jo00283a033

Reference yield:

: 194149-26-3
methyl 2,3:4,6-di-O-benzylidene-α-D-mannopyranoside

: 101199-50-2
methyl 4,6-O-benzylidene-2,3-dideoxy-2-C-(2-hydroxyethyl)-3-C-((Z)-2-hydroxyethylidene)-α-D-ribo-hexopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1: 1.) n-BuLi, 2.) hexamethylphosphoramide / 1.) THF, from -40 deg C to -30 deg C, 30 min, 2.) THF, from -35 deg C to -30 deg C

2: 98 percent / acetonitrile / 72 h / Heating

3: 71 percent / DIBAL / CH₂Cl₂

With N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; diisobutylaluminium hydride; In dichloromethane; acetonitrile;
DOI:10.1021/jo00283a033