phenyl 6-O-(tert-butyl(diphenyl)silyl)-1-thio-β-D-galactopyranoside

Base Information

• Chemical Name: phenyl 6-O-(tert-butyl(diphenyl)silyl)-1-thio-β-D-galactopyranoside
• CAS No.: 195316-81-5
• Molecular Formula: C₂₈H₃₄O₅SSi
• Molecular Weight: 510.726
• Mol file: 195316-81-5.mol

Synonyms:phenyl 6-O-(tert-butyl(diphenyl)silyl)-1-thio-β-D-galactopyranoside

Chemical Property of phenyl 6-O-(tert-butyl(diphenyl)silyl)-1-thio-β-D-galactopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of phenyl 6-O-(tert-butyl(diphenyl)silyl)-1-thio-β-D-galactopyranoside

There total 4 articles about phenyl 6-O-(tert-butyl(diphenyl)silyl)-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: 94.0%

1-thiophenyl-β-D-galactopyranoside (16758-34-2) + tert-butylchlorodiphenylsilane (58479-61-1) → phenyl 6-O-(tert-butyl(diphenyl)silyl)-1-thio-β-D-galactopyranoside (195316-81-5)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 45 ℃; for 3h; Inert atmosphere;

DOI:10.1039/b916580k

Reference yield:

1-deoxy-1-(phenylthio)-2,3,4,6-tetra-O-acetyl-β-D-galactopyranose (13992-16-0,23661-28-1,28512-68-7,65236-85-3,86782-39-0,108032-93-5,121524-01-4,121570-34-1,24404-53-3) → phenyl 6-O-(tert-butyl(diphenyl)silyl)-1-thio-β-D-galactopyranoside (195316-81-5)

Guidance literature:

Multi-step reaction with 2 steps

1: NaOMe / methanol / 0.5 h

2: pyridine / 2 h / 30 °C

With pyridine; sodium methylate; In methanol;

DOI:10.1081/CAR-200058529

Reference yield:

D-galactose pentaacetate (25878-60-8) → phenyl 6-O-(tert-butyl(diphenyl)silyl)-1-thio-β-D-galactopyranoside (195316-81-5)

Guidance literature:

Multi-step reaction with 3 steps

1: SnCl₄ / CH₂Cl₂ / 3.5 h / -15 °C

2: NaOMe / methanol / 1 h / 25 °C

3: imidazole / dimethylformamide / 1.5 h / 0 °C

With 1H-imidazole; sodium methylate; tin(IV) chloride; In methanol; dichloromethane; N,N-dimethyl-formamide; 1: sulfuration / 2: deacetylation / 3: silylation;

DOI:10.1002/1522-2675(20000809)83:8<1977::AID-HLCA1977>3.0.CO;2-D

upstream raw materials:

1-thiophenyl-β-D-galactopyranoside

tert-butylchlorodiphenylsilane

1-deoxy-1-(phenylthio)-2,3,4,6-tetra-O-acetyl-β-D-galactopyranose

D-galactose pentaacetate

Downstream raw materials:

phenyl 2,3,4-tri-O-benzoyl-6-O-tert-butyldiphenylsilyl-1-thio-β-D-galactopyranoside

phenyl 6-O-[(tert-butyl)diphenylsilyl]-3,4-O-isopropylidene-1-thio-β-D-galactopyranoside

phenyl 2,3,4-tri-O-acetyl-6-O-t-butylphenylsilyl-1-thio-β-D-galactopyranoside

2-(trimethylsilyl)ethyl-2,3,4-tri-O-acetyl-6-O-t-butyldiphenylsilyl-β-D-galactopyranosyl-(1->4)-3-O-acetyl-6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside