1-O-(tert-butyldimethylsilyl)-2-deoxy-2-azido-3,4,6-tri-O-benzyl-5-oxo-D-altritol

Base Information

• Chemical Name: 1-O-(tert-butyldimethylsilyl)-2-deoxy-2-azido-3,4,6-tri-O-benzyl-5-oxo-D-altritol
• CAS No.: 943860-59-1
• Molecular Formula: C₃₃H₄₃N₃O₅Si
• Molecular Weight: 589.807

Synonyms:1-O-(tert-butyldimethylsilyl)-2-deoxy-2-azido-3,4,6-tri-O-benzyl-5-oxo-D-altritol

Chemical Property of 1-O-(tert-butyldimethylsilyl)-2-deoxy-2-azido-3,4,6-tri-O-benzyl-5-oxo-D-altritol

Chemical Property:

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Technology Process of 1-O-(tert-butyldimethylsilyl)-2-deoxy-2-azido-3,4,6-tri-O-benzyl-5-oxo-D-altritol

There total 2 articles about 1-O-(tert-butyldimethylsilyl)-2-deoxy-2-azido-3,4,6-tri-O-benzyl-5-oxo-D-altritol 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: 91.0%

1-O-(tert-butyldimethylsilyl)-2-deoxy-2-azido-3,4,6-tri-O-benzyl-D-altritol (943860-58-0) → 1-O-(tert-butyldimethylsilyl)-2-deoxy-2-azido-3,4,6-tri-O-benzyl-5-oxo-D-altritol (943860-59-1)

Guidance literature:

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

DOI:10.1055/s-2007-966022

Reference yield:

2-deoxy-2-azido-3,4,6-tri-O-benzyl-D-altritol (881895-05-2) → 1-O-(tert-butyldimethylsilyl)-2-deoxy-2-azido-3,4,6-tri-O-benzyl-5-oxo-D-altritol (943860-59-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 95 percent / DMAP / pyridine / 20 °C

2: 91 percent / Dess-Martin periodinane / CH₂Cl₂ / 20 °C

With dmap; Dess-Martin periodane; In pyridine; dichloromethane;

DOI:10.1055/s-2007-966022

Reference yield:

1-O-(tert-butyldimethylsilyl)-2-deoxy-2-azido-3,4,6-tri-O-benzyl-5-oxo-D-altritol (943860-59-1) → C33H45N3O5Si

Guidance literature:

With sodium tetrahydroborate; In methanol; at 0 ℃; for 2h;

DOI:10.1055/s-2007-966022

upstream raw materials:

1-O-(tert-butyldimethylsilyl)-2-deoxy-2-azido-3,4,6-tri-O-benzyl-D-altritol

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

Downstream raw materials:

(2S,3S,4R,5S)-3,4-bis(benzyloxy)-2-[(benzyloxy)methyl]-5-[(tert-butyldimethylsiloxy)methyl]pyrrolidine

C₃₈H₅₃NO₆Si

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