phenyl 2,6-di-O-benzyl-3,4-O-[(2S,3S)-2,3-dimethoxybutan-2,3-diyl]-1-thio-α-D-mannopyranoside

Base Information

• Chemical Name: phenyl 2,6-di-O-benzyl-3,4-O-[(2S,3S)-2,3-dimethoxybutan-2,3-diyl]-1-thio-α-D-mannopyranoside
• CAS No.: 263543-43-7
• Molecular Formula: C₃₂H₃₈O₇S
• Molecular Weight: 566.716
• Mol file: 263543-43-7.mol

Synonyms:phenyl 2,6-di-O-benzyl-3,4-O-[(2S,3S)-2,3-dimethoxybutan-2,3-diyl]-1-thio-α-D-mannopyranoside

Chemical Property of phenyl 2,6-di-O-benzyl-3,4-O-[(2S,3S)-2,3-dimethoxybutan-2,3-diyl]-1-thio-α-D-mannopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of phenyl 2,6-di-O-benzyl-3,4-O-[(2S,3S)-2,3-dimethoxybutan-2,3-diyl]-1-thio-α-D-mannopyranoside

There total 4 articles about phenyl 2,6-di-O-benzyl-3,4-O-[(2S,3S)-2,3-dimethoxybutan-2,3-diyl]-1-thio-α-D-mannopyranoside 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: 99.0%

benzyl bromide (100-39-0) + phenyl 3,4-O-(2’,3’-dimethoxybutane-2’,3’-diyl)-1-thio-α-D-mannopyranoside (263543-42-6) → phenyl 2,6-di-O-benzyl-3,4-O-[(2S,3S)-2,3-dimethoxybutan-2,3-diyl]-1-thio-α-D-mannopyranoside (263543-43-7)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; at 20 ℃; for 1h;

DOI:10.1021/ol048525+

Reference yield: 81.0%

benzyl bromide (100-39-0) + phenyl 3,4-O-(2’,3’-dimethoxybutane-2’,3’-diyl)-1-thio-α-D-mannopyranoside (263543-42-6) → phenyl 2-O-benzyl-3,4-O-(2',3'-dimethoxybutane-2',3'-diyl)-1-thio-α-D-mannopyranoside (1060735-24-1) + phenyl 2,6-di-O-benzyl-3,4-O-[(2S,3S)-2,3-dimethoxybutan-2,3-diyl]-1-thio-α-D-mannopyranoside (263543-43-7)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; mineral oil; at -40 - -10 ℃; for 17h;

DOI:10.1021/jo801414c

Reference yield:

(2R,3S,4S,5S,6R)-2-Hydroxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3,4,5-triol (2936-70-1,5624-48-6,13992-15-9,16758-34-2,28244-97-5,77481-63-1,105088-17-3,149495-84-1,77481-62-0) → phenyl 2,6-di-O-benzyl-3,4-O-[(2S,3S)-2,3-dimethoxybutan-2,3-diyl]-1-thio-α-D-mannopyranoside (263543-43-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 7.2 g / (MeO)3CH; CSA / methanol / 14 h / Heating

2: 99 percent / NaH / dimethylformamide / 1 h / 20 °C

With camphor-10-sulfonic acid; sodium hydride; trimethyl orthoformate; In methanol; N,N-dimethyl-formamide;

DOI:10.1021/ol048525+

upstream raw materials:

benzyl bromide

phenyl 3,4-O-(2’,3’-dimethoxybutane-2’,3’-diyl)-1-thio-α-D-mannopyranoside

phenyl 2,3,4,6-tetra-O-acetyl-1-thio-α-D-mannopyranoside

(2R,3S,4S,5S,6R)-2-Hydroxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3,4,5-triol

Downstream raw materials:

2,6-di-O-benzyl-3,4-O-[(2S,3S)-2,3-dimethoxybutan-2,3-diyl]-D-mannolactone

(2S,3S,4aR,5R,7S,8S,8aS)-8-Benzyloxy-5-benzyloxymethyl-2,3-dimethoxy-2,3-dimethyl-7-phenyl-hexahydro-pyrano[3,4-b][1,4]dioxin-7-ol