(2S,3S,4R,5S,6R)-2-Allyloxy-5-(tert-butyl-diphenyl-silanyloxy)-6-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-pyran-3,4-diol

Base Information

• Chemical Name: (2S,3S,4R,5S,6R)-2-Allyloxy-5-(tert-butyl-diphenyl-silanyloxy)-6-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-pyran-3,4-diol
• CAS No.: 182187-83-3
• Molecular Formula: C₄₁H₅₂O₆Si₂
• Molecular Weight: 697.031
• Mol file: 182187-83-3.mol

Synonyms:

Chemical Property of (2S,3S,4R,5S,6R)-2-Allyloxy-5-(tert-butyl-diphenyl-silanyloxy)-6-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-pyran-3,4-diol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S,4R,5S,6R)-2-Allyloxy-5-(tert-butyl-diphenyl-silanyloxy)-6-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-pyran-3,4-diol

There total 2 articles about (2S,3S,4R,5S,6R)-2-Allyloxy-5-(tert-butyl-diphenyl-silanyloxy)-6-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-pyran-3,4-diol 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:

tert-butylchlorodiphenylsilane (58479-61-1) → (2S,3S,4R,5S,6R)-2-Allyloxy-5-(tert-butyl-diphenyl-silanyloxy)-6-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-pyran-3,4-diol (182187-83-3)

Guidance literature:

Multi-step reaction with 2 steps

1: imidazole / dimethylformamide / 8 h / 20 °C

2: 1.) n-BuLi, 2.) H₂O / 1.) hexane, THF, -76 deg C, 10 min

With 1H-imidazole; n-butyllithium; water; In N,N-dimethyl-formamide;

DOI:10.1016/0040-4020(96)00600-X

Reference yield:

(2S,3S,4S,5R,6R)-2-Allyloxy-4-(tert-butyl-diphenyl-silanyloxy)-6-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-pyran-3,5-diol (182187-85-5) → (2S,3S,4R,5S,6R)-2-Allyloxy-5-(tert-butyl-diphenyl-silanyloxy)-6-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-pyran-3,4-diol (182187-83-3) + (2R,3S,4S,5S,6S)-6-Allyloxy-5-(tert-butyl-diphenyl-silanyloxy)-2-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-pyran-3,4-diol (182187-87-7)

Guidance literature:

With n-butyllithium; water; Yield given. Multistep reaction. Title compound not separated from byproducts; 1.) hexane, THF, -76 deg C, 10 min;

DOI:10.1016/0040-4020(96)00600-X

Reference yield:

(2S,3S,4R,5S,6R)-2-Allyloxy-5-(tert-butyl-diphenyl-silanyloxy)-6-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-pyran-3,4-diol (182187-83-3) + methyl trifluoromethanesulfonate (333-27-7) → (2S,3S,4R,5R,6R)-2-Allyloxy-5-(tert-butyl-diphenyl-silanyloxy)-6-(tert-butyl-diphenyl-silanyloxymethyl)-3,4-dimethoxy-tetrahydro-pyran (182187-89-9)

Guidance literature:

With 2,6-di-tert-butyl-pyridine; In dichloromethane; at 80 ℃;

DOI:10.1016/0040-4020(96)00600-X

upstream raw materials:

(2S,3S,4S,5R,6R)-2-Allyloxy-4-(tert-butyl-diphenyl-silanyloxy)-6-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-pyran-3,5-diol

tert-butylchlorodiphenylsilane

Downstream raw materials:

(2S,3S,4R,5R,6R)-2-Allyloxy-5-(tert-butyl-diphenyl-silanyloxy)-6-(tert-butyl-diphenyl-silanyloxymethyl)-3,4-dimethoxy-tetrahydro-pyran