phenyl 2-O-(tert-butyldiphenylsilyl)-3,4-O-isopropylidene-1-thio-β-D-galactopyranoside

Base Information

• Chemical Name: phenyl 2-O-(tert-butyldiphenylsilyl)-3,4-O-isopropylidene-1-thio-β-D-galactopyranoside
• CAS No.: 171815-41-1
• Molecular Formula: C₃₁H₃₈O₅SSi
• Molecular Weight: 550.791

Synonyms:phenyl 2-O-(tert-butyldiphenylsilyl)-3,4-O-isopropylidene-1-thio-β-D-galactopyranoside

Chemical Property of phenyl 2-O-(tert-butyldiphenylsilyl)-3,4-O-isopropylidene-1-thio-β-D-galactopyranoside

Chemical Property:

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Technology Process of phenyl 2-O-(tert-butyldiphenylsilyl)-3,4-O-isopropylidene-1-thio-β-D-galactopyranoside

There total 3 articles about phenyl 2-O-(tert-butyldiphenylsilyl)-3,4-O-isopropylidene-1-thio-β-D-galactopyranoside 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: 86.0%

Acetic acid (3aS,4R,6S,7R,7aS)-7-(tert-butyl-diphenyl-silanyloxy)-2,2-dimethyl-6-phenylsulfanyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-ylmethyl ester (171815-43-3) → phenyl 2-O-(tert-butyldiphenylsilyl)-3,4-O-isopropylidene-1-thio-β-D-galactopyranoside (171815-41-1)

Guidance literature:

With sodium methylate; In methanol; for 1h;

DOI:10.1021/jo00126a065

Reference yield:

tert-butylchlorodiphenylsilane (58479-61-1) → phenyl 2-O-(tert-butyldiphenylsilyl)-3,4-O-isopropylidene-1-thio-β-D-galactopyranoside (171815-41-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 85 percent / imidazole, DMAP / dimethylformamide / 20 h / Ambient temperature

2: 86 percent / MeONa / methanol / 1 h

With 1H-imidazole; dmap; sodium methylate; In methanol; N,N-dimethyl-formamide;

DOI:10.1021/jo00126a065

Reference yield:

phenyl 6-O-acetyl-3,4-O-isopropylidene-1-thio-β-D-galactopyranoside (171815-42-2) → phenyl 2-O-(tert-butyldiphenylsilyl)-3,4-O-isopropylidene-1-thio-β-D-galactopyranoside (171815-41-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 85 percent / imidazole, DMAP / dimethylformamide / 20 h / Ambient temperature

2: 86 percent / MeONa / methanol / 1 h

With 1H-imidazole; dmap; sodium methylate; In methanol; N,N-dimethyl-formamide;

DOI:10.1021/jo00126a065

upstream raw materials:

Acetic acid (3aS,4R,6S,7R,7aS)-7-(tert-butyl-diphenyl-silanyloxy)-2,2-dimethyl-6-phenylsulfanyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-ylmethyl ester

tert-butylchlorodiphenylsilane

phenyl 6-O-acetyl-3,4-O-isopropylidene-1-thio-β-D-galactopyranoside

Downstream raw materials:

phenyl 6-O-(6-O-acetyl-2-O-(tert-butyldiphenylsilyl)-3,4-O-isopropylidene-α-D-galactopyranosyl)-2-O-(tert-butyldiphenylsilyl)-3,4-O-isopropylidene-1-thio-β-D-galactopyranoside

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