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

Base Information

• Chemical Name: phenyl 6-O-tert-butyldimethylsilyl-3,4-O-isopropylidene-1-thio-β-D-galactopyranoside
• CAS No.: 940941-28-6
• Molecular Formula: C₂₁H₃₄O₅SSi
• Molecular Weight: 426.649
• Mol file: 940941-28-6.mol

Synonyms:phenyl 6-O-tert-butyldimethylsilyl-3,4-O-isopropylidene-1-thio-β-D-galactopyranoside

Chemical Property of phenyl 6-O-tert-butyldimethylsilyl-3,4-O-isopropylidene-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-butyldimethylsilyl-3,4-O-isopropylidene-1-thio-β-D-galactopyranoside

There total 3 articles about phenyl 6-O-tert-butyldimethylsilyl-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: 92.0%

tert-butyldimethylsilyl chloride (18162-48-6) + phenyl 3,4-O-isopropylidene-1-thio-β-D-galactopyranoside (120095-47-8) → phenyl 6-O-tert-butyldimethylsilyl-3,4-O-isopropylidene-1-thio-β-D-galactopyranoside (940941-28-6)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 20 ℃; for 20h;

DOI:10.1016/j.tet.2007.03.051

Reference yield:

1-thiophenyl-β-D-galactopyranoside (16758-34-2) → phenyl 6-O-tert-butyldimethylsilyl-3,4-O-isopropylidene-1-thio-β-D-galactopyranoside (940941-28-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 3.76 g / TsOH / dimethylformamide / 16 h / pH 2

2: 92 percent / DMAP; Et₃N / CH₂Cl₂ / 20 h / 20 °C

With dmap; toluene-4-sulfonic acid; triethylamine; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.tet.2007.03.051

Reference yield:

(2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(phenylthio)tetrahydro-2H-pyran-3,4,5-triyl triacetate (13992-16-0,23661-28-1,24404-53-3,28512-68-7,65236-85-3,86782-39-0,108032-93-5,121524-01-4,121570-34-1) → phenyl 6-O-tert-butyldimethylsilyl-3,4-O-isopropylidene-1-thio-β-D-galactopyranoside (940941-28-6)

Guidance literature:

Multi-step reaction with 3 steps

1: NaOMe / methanol

2: 3.76 g / TsOH / dimethylformamide / 16 h / pH 2

3: 92 percent / DMAP; Et₃N / CH₂Cl₂ / 20 h / 20 °C

With dmap; sodium methylate; toluene-4-sulfonic acid; triethylamine; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.tet.2007.03.051

upstream raw materials:

tert-butyldimethylsilyl chloride

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

1-thiophenyl-β-D-galactopyranoside

(2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(phenylthio)tetrahydro-2H-pyran-3,4,5-triyl triacetate

Downstream raw materials:

phenyl 2-O-benzyl-1-thio-β-D-galactopyranoside

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

phenyl 2-O-benzyl-6-O-tert-butyldimethylsilyl-3,4-O-isopropylidene-1-thio-β-D-galactopyranoside