phenyl 2,3,4-tri-O-benzyl-6-O-(tert-butyldimethylsilyl)-1-thio-α-D-mannopyranoside

Base Information

• Chemical Name: phenyl 2,3,4-tri-O-benzyl-6-O-(tert-butyldimethylsilyl)-1-thio-α-D-mannopyranoside
• CAS No.: 588730-45-4
• Molecular Formula: C₃₉H₄₈O₅SSi
• Molecular Weight: 656.959

Synonyms:phenyl 2,3,4-tri-O-benzyl-6-O-(tert-butyldimethylsilyl)-1-thio-α-D-mannopyranoside

Chemical Property of phenyl 2,3,4-tri-O-benzyl-6-O-(tert-butyldimethylsilyl)-1-thio-α-D-mannopyranoside

Chemical Property:

Purity/Quality:

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Technology Process of phenyl 2,3,4-tri-O-benzyl-6-O-(tert-butyldimethylsilyl)-1-thio-α-D-mannopyranoside

There total 5 articles about phenyl 2,3,4-tri-O-benzyl-6-O-(tert-butyldimethylsilyl)-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: 92.0%

benzyl bromide (100-39-0) + phenyl 6-O-(tert-butyldimethylsilyloxy)-1-thio-α-D-mannopyranoside (152488-25-0) → phenyl 2,3,4-tri-O-benzyl-6-O-(tert-butyldimethylsilyl)-1-thio-α-D-mannopyranoside (588730-45-4)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; at 0 ℃; for 1h;

DOI:10.1016/S0040-4020(03)00615-X

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 2,3,4-tri-O-benzyl-6-O-(tert-butyldimethylsilyl)-1-thio-α-D-mannopyranoside (588730-45-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 72 percent / imidazole / dimethylformamide / 0.17 h / 0 °C

2: 92 percent / NaH / dimethylformamide / 1 h / 0 °C

With 1H-imidazole; sodium hydride; In N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(03)00615-X

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → phenyl 2,3,4-tri-O-benzyl-6-O-(tert-butyldimethylsilyl)-1-thio-α-D-mannopyranoside (588730-45-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 72 percent / imidazole / dimethylformamide / 0.17 h / 0 °C

2: 92 percent / NaH / dimethylformamide / 1 h / 0 °C

With 1H-imidazole; sodium hydride; In N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(03)00615-X

upstream raw materials:

benzyl bromide

phenyl 6-O-(tert-butyldimethylsilyloxy)-1-thio-α-D-mannopyranoside

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

tert-butyldimethylsilyl chloride

Downstream raw materials:

phenyl 2,3,4-tri-O-benzyl-1-thio-α-D-mannopyranoside

allyl [2,3,4-tri-O-benzyl-6-O-(tert-butyldimethylsilyl)-α-D-mannopyranosyl]-(1->2)-3,4,6-tri-O-benzyl-α-D-mannopyranoside

allyl (2,3,4-tri-O-benzyl-6-O-{[2-(benzyloxycarbonylamino)ethyl](2-cyanoethyl)phosphonato}-α-D-mannopyranosyl)-(1->2)-3,4,6-tri-O-benzyl-α-D-mannopyranoside

allyl (2,3,4-tri-O-benzyl-α-D-mannopyranosyl)-(1->2)-3,4,6-tri-O-benzyl-α-D-mannopyranoside

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