phenyl 3-O-benzyl-4,6-O-benzylidene-2-O-trimethylsilyl-1-thio-β-D-glucopyranoside

Base Information

• Chemical Name: phenyl 3-O-benzyl-4,6-O-benzylidene-2-O-trimethylsilyl-1-thio-β-D-glucopyranoside
• CAS No.: 128848-52-2
• Molecular Formula: C₂₉H₃₄O₅SSi
• Molecular Weight: 522.737
• Mol file: 128848-52-2.mol

Synonyms:phenyl 3-O-benzyl-4,6-O-benzylidene-2-O-trimethylsilyl-1-thio-β-D-glucopyranoside

Chemical Property of phenyl 3-O-benzyl-4,6-O-benzylidene-2-O-trimethylsilyl-1-thio-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of phenyl 3-O-benzyl-4,6-O-benzylidene-2-O-trimethylsilyl-1-thio-β-D-glucopyranoside

There total 3 articles about phenyl 3-O-benzyl-4,6-O-benzylidene-2-O-trimethylsilyl-1-thio-β-D-glucopyranoside 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: 98.0%

chloro-trimethyl-silane (75-77-4) + phenyl 3-O-benzyl-4,6-O-benzylidene-1-deoxy-1-thio-β-D-glucopyranoside (128848-51-1) → phenyl 3-O-benzyl-4,6-O-benzylidene-2-O-trimethylsilyl-1-thio-β-D-glucopyranoside (128848-52-2)

Guidance literature:

With pyridine; 1,1,1,3,3,3-hexamethyl-disilazane; at 60 ℃; for 0.5h;

DOI:10.1016/S0040-4020(01)97585-4

Reference yield:

benzyl bromide (100-39-0) → phenyl 3-O-benzyl-4,6-O-benzylidene-2-O-trimethylsilyl-1-thio-β-D-glucopyranoside (128848-52-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 1)Bu₂SnO, 2)tetrabutylammonium bromide / 1)acetonitrile, 4 Angstroem molecular sieves, refluxed for 4h, 2)refluxed for 13h

2: 98 percent / hexamethyldisilazane, pyridine / 0.5 h / 60 °C

With pyridine; tetrabutylammomium bromide; di(n-butyl)tin oxide; 1,1,1,3,3,3-hexamethyl-disilazane;

DOI:10.1016/S0040-4020(01)97585-4

Reference yield:

(2R,4aR,6S,7R,8R,8aS)-2-Phenyl-6-phenylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol (71676-30-7,87508-18-7,138922-03-9,87508-17-6) → phenyl 3-O-benzyl-4,6-O-benzylidene-2-O-trimethylsilyl-1-thio-β-D-glucopyranoside (128848-52-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 1)Bu₂SnO, 2)tetrabutylammonium bromide / 1)acetonitrile, 4 Angstroem molecular sieves, refluxed for 4h, 2)refluxed for 13h

2: 98 percent / hexamethyldisilazane, pyridine / 0.5 h / 60 °C

With pyridine; tetrabutylammomium bromide; di(n-butyl)tin oxide; 1,1,1,3,3,3-hexamethyl-disilazane;

DOI:10.1016/S0040-4020(01)97585-4

upstream raw materials:

chloro-trimethyl-silane

phenyl 3-O-benzyl-4,6-O-benzylidene-1-deoxy-1-thio-β-D-glucopyranoside

(2R,4aR,6S,7R,8R,8aS)-2-Phenyl-6-phenylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol

benzyl bromide

Downstream raw materials:

(3-O-benzyl-4,6-O-benzylidene-α-D-glucopyranosyl)trimethylsilane

1,5-anhydro-3-O-benzyl-4,6-O-benzylidene-2-deoxy-D-arabino-hex-1-enitol