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

Base Information

• Chemical Name: phenyl 3,4-O-(2’,3’-dimethoxybutane-2’,3’-diyl)-1-thio-α-D-mannopyranoside
• CAS No.: 263543-42-6
• Molecular Formula: C₁₈H₂₆O₇S
• Molecular Weight: 386.466
• Mol file: 263543-42-6.mol

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

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

There total 3 articles about phenyl 3,4-O-(2’,3’-dimethoxybutane-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: 66.0%

(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) + dimethylglyoxal (431-03-8) + trimethyl orthoformate (149-73-5) → phenyl 3,4-O-(2’,3’-dimethoxybutane-2’,3’-diyl)-1-thio-α-D-mannopyranoside (263543-42-6)

Guidance literature:

With camphor-10-sulfonic acid; In methanol; for 72h; Heating;

DOI:10.1021/jo9910482

Reference yield:

phenyl 2,3,4,6-tetra-O-acetyl-1-thio-α-D-mannopyranoside (13992-16-0,23661-28-1,24404-53-3,28512-68-7,65236-85-3,86782-39-0,121524-01-4,121570-34-1,108032-93-5) → phenyl 3,4-O-(2’,3’-dimethoxybutane-2’,3’-diyl)-1-thio-α-D-mannopyranoside (263543-42-6)

Guidance literature:

Multi-step reaction with 2 steps

1: NaOMe / methanol / 0.5 h / 20 °C

2: 7.2 g / (MeO)3CH; CSA / methanol / 14 h / Heating

With camphor-10-sulfonic acid; sodium methylate; trimethyl orthoformate; In methanol;

DOI:10.1021/ol048525+

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) + 2,2,3,3-tetramethoxybutane (176798-33-7) → phenyl 3,4-O-(2’,3’-dimethoxybutane-2’,3’-diyl)-1-thio-α-D-mannopyranoside (263543-42-6)

Guidance literature:

With camphor-10-sulfonic acid; trimethyl orthoformate; In methanol; for 14h; Heating;

DOI:10.1021/ol048525+

upstream raw materials:

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

dimethylglyoxal

trimethyl orthoformate

2,2,3,3-tetramethoxybutane

Downstream raw materials:

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

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