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

Base Information

Chemical Name: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
CAS No.:171815-47-7
Molecular Formula:C₅₈H₇₂O₁₁SSi₂
Molecular Weight:1033.44
Hs Code.:

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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Chemical Property of 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

Chemical Property:

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Technology Process of 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

There total 4 articles about 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 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:

: 58479-61-1
tert-butylchlorodiphenylsilane

: 171815-47-7
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

Guidance literature:: Multi-step reaction with 3 steps

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

2: 86 percent / MeONa / methanol / 1 h

3: 1.) Tf₂O, 2.) 2,6-di-tert-butyl-4-methylpyridine / 1.) Et₂O, CH₂Cl₂, -78 deg C, 15 min, 2.) Et₂O, CH₂Cl₂, -78 deg C, 1 h

With 1H-imidazole; dmap; 2,6-di-tert-butyl-4-methylpyridine; trifluoromethylsulfonic anhydride; sodium methylate; In methanol; N,N-dimethyl-formamide;
DOI:10.1021/jo00126a065

Reference yield:

: 171815-42-2
phenyl 6-O-acetyl-3,4-O-isopropylidene-1-thio-β-D-galactopyranoside

: 171815-47-7
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

Guidance literature:: Multi-step reaction with 3 steps

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

2: 86 percent / MeONa / methanol / 1 h

3: 1.) Tf₂O, 2.) 2,6-di-tert-butyl-4-methylpyridine / 1.) Et₂O, CH₂Cl₂, -78 deg C, 15 min, 2.) Et₂O, CH₂Cl₂, -78 deg C, 1 h

With 1H-imidazole; dmap; 2,6-di-tert-butyl-4-methylpyridine; trifluoromethylsulfonic anhydride; sodium methylate; In methanol; N,N-dimethyl-formamide;
DOI:10.1021/jo00126a065

Reference yield:

: 171815-43-3
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

: 171815-47-7
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

Guidance literature:: Multi-step reaction with 2 steps

1: 86 percent / MeONa / methanol / 1 h

2: 1.) Tf₂O, 2.) 2,6-di-tert-butyl-4-methylpyridine / 1.) Et₂O, CH₂Cl₂, -78 deg C, 15 min, 2.) Et₂O, CH₂Cl₂, -78 deg C, 1 h

With 2,6-di-tert-butyl-4-methylpyridine; trifluoromethylsulfonic anhydride; sodium methylate; In methanol;
DOI:10.1021/jo00126a065