methyl 4,6-O-benzylidene-2,3-dideoxy-2-C-methyl-α-D-arabino-hexo pyranoside

Base Information

• Chemical Name: methyl 4,6-O-benzylidene-2,3-dideoxy-2-C-methyl-α-D-arabino-hexo pyranoside
• CAS No.: 93381-10-3
• Molecular Formula: C₁₅H₂₀O₄
• Molecular Weight: 264.321
• Mol file: 93381-10-3.mol

Synonyms:methyl 4,6-O-benzylidene-2,3-dideoxy-2-C-methyl-α-D-arabino-hexo pyranoside

Chemical Property of methyl 4,6-O-benzylidene-2,3-dideoxy-2-C-methyl-α-D-arabino-hexo pyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 4,6-O-benzylidene-2,3-dideoxy-2-C-methyl-α-D-arabino-hexo pyranoside

There total 5 articles about methyl 4,6-O-benzylidene-2,3-dideoxy-2-C-methyl-α-D-arabino-hexo pyranoside 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: 67.0%

methyl 4,6-O-benzylidene-2,3-dideoxy-2-C-methylene-α-D-erythro-hexopyranoside (35905-41-0) → methyl 4,6-O-benzylidene-2,3-dideoxy-2-C-methyl-α-D-arabino-hexo pyranoside (93381-10-3) + methyl 2,3-dideoxy-4,6-O-benzylidene-2-methyl-α-D-glucopyranoside (90365-11-0)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; Yields of byproduct given;

DOI:10.1016/S0040-4039(01)80352-X

Reference yield: 62.0%

methyl 4,6-O-benzylidene-2-deoxy-2-C-methyl-3.O-<(thiomethyl)-thiocarbonyl>-α-D-altro-pyranoside (56981-18-1) → methyl 4,6-O-benzylidene-2,3-dideoxy-2-C-methyl-α-D-arabino-hexo pyranoside (93381-10-3)

Guidance literature:

With tri-n-butyl-tin hydride; In toluene; Heating;

DOI:10.1016/S0040-4020(01)87081-2

Reference yield:

methyl 4,6-O-benzylidene-2-deoxy-2-C-methyl-α-D-altro-pyranoside (19465-06-6) → methyl 4,6-O-benzylidene-2,3-dideoxy-2-C-methyl-α-D-arabino-hexo pyranoside (93381-10-3)

Guidance literature:

Multi-step reaction with 2 steps

1: toluene / 4 h / Heating

2: tri-n-butylstannane, AIBN / toluene / Heating

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In toluene;

DOI:10.1021/jo00363a046

upstream raw materials:

methyl 4,6-O-benzylidene-2,3-dideoxy-2-C-methylene-α-D-erythro-hexopyranoside

methyl 4,6-O-benzylidene-2-deoxy-2-C-methyl-3.O-<(thiomethyl)-thiocarbonyl>-α-D-altro-pyranoside

2-Oxo-2H-pyridine-1-carbothioic acid O-((4aR,6S,7S,8S,8aS)-6-methoxy-7-methyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl) ester

methyl 4,6-O-benzylidene-2-deoxy-2-C-methyl-α-D-altro-pyranoside

Downstream raw materials:

methyl 2,3-dideoxy-2-C-methyl-6-O-(triphenylmethyl)-α-D-arabino-hexopyranoside

Chloro-acetic acid (2R,3S,5S,6S)-6-methoxy-5-methyl-2-trityloxymethyl-tetrahydro-pyran-3-yl ester

methyl 4-O-bromoacetyl-2,3-dideoxy-2-C-methyl-6-O-triphenylmethyl-α-D-arabino-hexopyranoside

methyl 2,3-dideoxy-4-O-(diethyl phosponoacetyl)-2-C-methyl-6-O-triphenyl-α-D-arabino-hexo-pyranoside