1-(tert-butyl-dimethyl-sylanyloxy)-2-deoxy-2-azido-3,4,6-tri-O-benzyl-D-mannitol

Base Information

• Chemical Name: 1-(tert-butyl-dimethyl-sylanyloxy)-2-deoxy-2-azido-3,4,6-tri-O-benzyl-D-mannitol
• CAS No.: 765308-78-9
• Molecular Formula: C₃₃H₄₅N₃O₅Si
• Molecular Weight: 591.823
• Mol file: 765308-78-9.mol

Synonyms:1-(tert-butyl-dimethyl-sylanyloxy)-2-deoxy-2-azido-3,4,6-tri-O-benzyl-D-mannitol

Chemical Property of 1-(tert-butyl-dimethyl-sylanyloxy)-2-deoxy-2-azido-3,4,6-tri-O-benzyl-D-mannitol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-(tert-butyl-dimethyl-sylanyloxy)-2-deoxy-2-azido-3,4,6-tri-O-benzyl-D-mannitol

There total 1 articles about 1-(tert-butyl-dimethyl-sylanyloxy)-2-deoxy-2-azido-3,4,6-tri-O-benzyl-D-mannitol 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: 71.0%

2-deoxy-2-azido-3,4,6-tri-O-benzyl-D-mannitol (765308-77-8) + tert-butyldimethylsilyl chloride (18162-48-6) → 1-(tert-butyl-dimethyl-sylanyloxy)-2-deoxy-2-azido-3,4,6-tri-O-benzyl-D-mannitol (765308-78-9)

Guidance literature:

With pyridine; at 0 ℃;

DOI:10.1021/jo049355h

Reference yield: 91.0%

1-(tert-butyl-dimethyl-sylanyloxy)-2-deoxy-2-azido-3,4,6-tri-O-benzyl-D-mannitol (765308-78-9) → 1-(tert-butyl-dimethyl-sylanyloxy)-2-deoxy-2-azido-3,4,6-tri-O-benzyl-5-oxo-D-mannitol (765308-79-0)

Guidance literature:

With Dess-Martin periodane; In dichloromethane; at 0 - 20 ℃;

DOI:10.1021/jo049355h

Reference yield:

1-(tert-butyl-dimethyl-sylanyloxy)-2-deoxy-2-azido-3,4,6-tri-O-benzyl-D-mannitol (765308-78-9) → (2R,3R,4R,5S)-2-(tert-butyl-dimethyl-sylanyloxy-methyl)-3,4-di-O-benzyl-5-(O-benzyl-methyl)-pyrrolidine

Guidance literature:

Multi-step reaction with 3 steps

1: 91 percent / Dess-Martin reagent / CH₂Cl₂ / 0 - 20 °C

2: hydrogen / Pd-C / tetrahydrofuran; pyridine / 4 h / 760 Torr

3: 70 mg / NaBH₃CN; p-TsOH / methanol / 20 °C

With hydrogen; sodium cyanoborohydride; Dess-Martin periodane; toluene-4-sulfonic acid; palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol; dichloromethane;

DOI:10.1021/jo049355h

upstream raw materials:

2-deoxy-2-azido-3,4,6-tri-O-benzyl-D-mannitol

tert-butyldimethylsilyl chloride

Downstream raw materials:

1-(tert-butyl-dimethyl-sylanyloxy)-2-deoxy-2-azido-3,4,6-tri-O-benzyl-5-oxo-D-mannitol

(2R,3R,4R,5R)-2-(azido-methyl)-3,4-di-O-benzyl-5-(O-benzyl-methyl)-pyrrolidine

(2R,3R,4R,5R)-2-(tert-butyl-dimethyl-sylanyloxy-methyl)-3,4-di-O-benzyl-5-(O-benzyl-methyl)-pyrrolidine

(2S,3R,4R,5R)-5-Azido-1,3,4-tris-benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-hexan-2-ol