Phenyl 3-O-[(4-methoxyphenyl)methyl]-4,6-O-[(R)-phenylmethylene]-1-thio-alpha-D-mannopyranoside

Base Information

• Chemical Name: Phenyl 3-O-[(4-methoxyphenyl)methyl]-4,6-O-[(R)-phenylmethylene]-1-thio-alpha-D-mannopyranoside
• CAS No.: 168138-26-9
• Molecular Formula: C27H28O6S
• Molecular Weight: 480.582
• Mol file: 168138-26-9.mol

Synonyms:Phenyl 3-O-[(4-methoxyphenyl)methyl]-4,6-O-[(R)-phenylmethylene]-1-thio-alpha-D-mannopyranoside

Chemical Property of Phenyl 3-O-[(4-methoxyphenyl)methyl]-4,6-O-[(R)-phenylmethylene]-1-thio-alpha-D-mannopyranoside

Chemical Property:

Purity/Quality:

95% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Phenyl 3-O-[(4-methoxyphenyl)methyl]-4,6-O-[(R)-phenylmethylene]-1-thio-alpha-D-mannopyranoside

There total 8 articles about Phenyl 3-O-[(4-methoxyphenyl)methyl]-4,6-O-[(R)-phenylmethylene]-1-thio-alpha-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: 94.0%

p-methoxybenzyl chloride (824-94-2) + phenyl 4,6-O-benzylidene-1-thio-α-D-mannopyranoside (159407-19-9) → phenyl 4,6-O-benzylidene-3-O-(4-methoxybenzyl)-1-thio-α-D-mannopyranoside (168138-26-9)

Guidance literature:

phenyl 4,6-O-benzylidene-1-thio-α-D-mannopyranoside; With di(n-butyl)tin oxide; In toluene; for 3h; Heating;

p-methoxybenzyl chloride; With tetrabutylammomium bromide; cesium fluoride; In toluene; for 3h; Heating;

DOI:10.1021/ja0471931

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 4,6-O-benzylidene-3-O-(4-methoxybenzyl)-1-thio-α-D-mannopyranoside (168138-26-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 57 percent / p-TsOH / dimethylformamide / 2 h / 60 °C

2.1: Bu₂SnO / toluene / 3 h / Heating

2.2: 94 percent / Bu₄NBr; CsF / toluene / 3 h / Heating

With di(n-butyl)tin oxide; toluene-4-sulfonic acid; In N,N-dimethyl-formamide; toluene;

DOI:10.1021/ja0471931

Reference yield:

benzaldehyde dimethyl acetal (1125-88-8) → phenyl 4,6-O-benzylidene-3-O-(4-methoxybenzyl)-1-thio-α-D-mannopyranoside (168138-26-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 57 percent / p-TsOH / dimethylformamide / 2 h / 60 °C

2.1: Bu₂SnO / toluene / 3 h / Heating

2.2: 94 percent / Bu₄NBr; CsF / toluene / 3 h / Heating

With di(n-butyl)tin oxide; toluene-4-sulfonic acid; In N,N-dimethyl-formamide; toluene;

DOI:10.1021/ja0471931

upstream raw materials:

p-methoxybenzyl chloride

phenyl 4,6-O-benzylidene-1-thio-α-D-mannopyranoside

p-Methoxybenzyl bromide

benzaldehyde dimethyl acetal

Downstream raw materials:

methyl 2-O-benzyl-4,6-O-benzylidene-3-O-p-methoxybenzyl-1-thio-α-D-mannopyranoside

tert-Butyl-[(2R,4aR,6R,7S,8S,8aR)-8-(4-methoxy-benzyloxy)-2-phenyl-6-phenylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yloxy]-dimethyl-silane

phenyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl-(1→2)-3,4,6-tri-Oacetyl-1-thio-α-D-mannopyranoside

2-azidoethyl (4,6-O-benzylidene-2,3-di-O-(p-methoxybenzyl)-β-D-mannopyranosyl)-(1→2)-4,6-O-benzylidene-3-O-(p-methoxybenzyl)-β-D-mannopyranoside