1-deoxy-1-α-hydroxymethyl-2-O-(tert-butyldimethylsilyl)-3,4,5-tri-O-benzyl-D-glucose

Base Information

• Chemical Name: 1-deoxy-1-α-hydroxymethyl-2-O-(tert-butyldimethylsilyl)-3,4,5-tri-O-benzyl-D-glucose
• CAS No.: 908838-46-0
• Molecular Formula: C₃₄H₄₆O₆Si
• Molecular Weight: 578.821
• Mol file: 908838-46-0.mol

Synonyms:1-deoxy-1-α-hydroxymethyl-2-O-(tert-butyldimethylsilyl)-3,4,5-tri-O-benzyl-D-glucose

Chemical Property of 1-deoxy-1-α-hydroxymethyl-2-O-(tert-butyldimethylsilyl)-3,4,5-tri-O-benzyl-D-glucose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-deoxy-1-α-hydroxymethyl-2-O-(tert-butyldimethylsilyl)-3,4,5-tri-O-benzyl-D-glucose

There total 4 articles about 1-deoxy-1-α-hydroxymethyl-2-O-(tert-butyldimethylsilyl)-3,4,5-tri-O-benzyl-D-glucose 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: 54.0%

1-deoxy-1-α-ethenyl-2-O-(tert-butyldimethylsilyl)-3,4,5-tri-O-benzyl-D-glucose (908838-45-9) → 1-deoxy-1-α-hydroxymethyl-2-O-(tert-butyldimethylsilyl)-3,4,5-tri-O-benzyl-D-glucose (908838-46-0)

Guidance literature:

1-deoxy-1-α-ethenyl-2-O-(tert-butyldimethylsilyl)-3,4,5-tri-O-benzyl-D-glucose; With ozone; In dichloromethane; at -78 ℃;

With methanol; sodium tetrahydroborate; In dichloromethane; at 0 - 20 ℃;

DOI:10.1016/j.carres.2006.05.008

Reference yield:

3,4,6-tri-O-benzyl-D-glucal (55628-54-1) → 1-deoxy-1-α-hydroxymethyl-2-O-(tert-butyldimethylsilyl)-3,4,5-tri-O-benzyl-D-glucose (908838-46-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 3,3-dimethyldioxirane / CH₂Cl₂

1.2: CH₂Cl₂ / -63 °C

2.1: 95 percent / 2,6-lutidine / CH₂Cl₂ / 0 - 20 °C

3.1: O₃ / CH₂Cl₂ / -78 °C

3.2: 54 percent / NaBH₄; MeOH / CH₂Cl₂ / 0 - 20 °C

With 2,6-dimethylpyridine; 3,3-dimethyldioxirane; ozone; In dichloromethane;

DOI:10.1016/j.carres.2006.05.008

Reference yield:

t-butyldimethylsiyl triflate (69739-34-0) → 1-deoxy-1-α-hydroxymethyl-2-O-(tert-butyldimethylsilyl)-3,4,5-tri-O-benzyl-D-glucose (908838-46-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 95 percent / 2,6-lutidine / CH₂Cl₂ / 0 - 20 °C

2.1: O₃ / CH₂Cl₂ / -78 °C

2.2: 54 percent / NaBH₄; MeOH / CH₂Cl₂ / 0 - 20 °C

With 2,6-dimethylpyridine; ozone; In dichloromethane;

DOI:10.1016/j.carres.2006.05.008

upstream raw materials:

1-deoxy-1-α-ethenyl-2-O-(tert-butyldimethylsilyl)-3,4,5-tri-O-benzyl-D-glucose

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

t-butyldimethylsiyl triflate

(2α,3S,4R,5R,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-2-vinyltetrahydro-2H-pyran-3-ol

Downstream raw materials:

C₃₄H₄₂NO₉P

(((2S,3R,4S,5R,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-2-(iodomethyl)tetrahydro-2H-pyran-3-yl)oxy)(tert-butyl)dimethylsilane

diethyl (((2S,3R,4S,5R,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-3-((tert-butyldimethylsilyl)oxy)tetrahydro-2H-pyran-2-yl)methyl)phosphonate

Methanesulfonic acid (2R,3S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-ylmethyl ester