((2S,3S,4S,5R,6R)-2-allyl-4,5-bis(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran-3-yloxy)(tert-butyl)dimethylsilane

Base Information

• Chemical Name: ((2S,3S,4S,5R,6R)-2-allyl-4,5-bis(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran-3-yloxy)(tert-butyl)dimethylsilane
• CAS No.: 1015481-45-4
• Molecular Formula: C₃₆H₄₈O₅Si
• Molecular Weight: 588.86
• Mol file: 1015481-45-4.mol

Synonyms:((2S,3S,4S,5R,6R)-2-allyl-4,5-bis(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran-3-yloxy)(tert-butyl)dimethylsilane

Chemical Property of ((2S,3S,4S,5R,6R)-2-allyl-4,5-bis(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran-3-yloxy)(tert-butyl)dimethylsilane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ((2S,3S,4S,5R,6R)-2-allyl-4,5-bis(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran-3-yloxy)(tert-butyl)dimethylsilane

There total 3 articles about ((2S,3S,4S,5R,6R)-2-allyl-4,5-bis(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran-3-yloxy)(tert-butyl)dimethylsilane 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: 97.0%

t-butyldimethylsiyl triflate (69739-34-0) + 3-(3,4,6-tri-O-benzyl-β-D-glucopyranosyl)-1-propene (161275-25-8) → ((2S,3S,4S,5R,6R)-2-allyl-4,5-bis(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran-3-yloxy)(tert-butyl)dimethylsilane (1015481-45-4)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; at 0 ℃;

Reference yield:

3,4,6-tri-O-benzyl-D-glucal (55628-54-1) → ((2S,3S,4S,5R,6R)-2-allyl-4,5-bis(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran-3-yloxy)(tert-butyl)dimethylsilane (1015481-45-4)

Guidance literature:

Multi-step reaction with 3 steps

1: dimethyldioxirane / CH₂Cl₂ / 0 °C

2: diethyl ether / -78 °C

3: Et₃N / CH₂Cl₂ / 20 °C

With 3,3-dimethyldioxirane; triethylamine; In diethyl ether; dichloromethane;

DOI:10.1016/j.bmcl.2007.04.060

Reference yield:

glucal epoxide (1011723-04-8) → ((2S,3S,4S,5R,6R)-2-allyl-4,5-bis(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran-3-yloxy)(tert-butyl)dimethylsilane (1015481-45-4)

Guidance literature:

Multi-step reaction with 2 steps

1: diethyl ether / -78 °C

2: Et₃N / CH₂Cl₂ / 20 °C

With triethylamine; In diethyl ether; dichloromethane;

DOI:10.1016/j.bmcl.2007.04.060

upstream raw materials:

t-butyldimethylsiyl triflate

3-(3,4,6-tri-O-benzyl-β-D-glucopyranosyl)-1-propene

3,4,6-tri-O-benzyl-D-glucal

glucal epoxide

Downstream raw materials:

C₃₅H₄₆O₆Si

3-C-(3,4,6-tri-O-benzyl-β-D-glucopyranosyl)1-propanol