5-azido-3,4-di-O-benzyl-5-deoxy-1,2-O-isopropylidene-β-D-psicopyranose

Base Information

• Chemical Name: 5-azido-3,4-di-O-benzyl-5-deoxy-1,2-O-isopropylidene-β-D-psicopyranose
• CAS No.: 872345-46-5
• Molecular Formula: C₂₃H₂₇N₃O₅
• Molecular Weight: 425.484
• Mol file: 872345-46-5.mol

Synonyms:5-azido-3,4-di-O-benzyl-5-deoxy-1,2-O-isopropylidene-β-D-psicopyranose

Chemical Property of 5-azido-3,4-di-O-benzyl-5-deoxy-1,2-O-isopropylidene-β-D-psicopyranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-azido-3,4-di-O-benzyl-5-deoxy-1,2-O-isopropylidene-β-D-psicopyranose

There total 6 articles about 5-azido-3,4-di-O-benzyl-5-deoxy-1,2-O-isopropylidene-β-D-psicopyranose 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: 72.0%

5-azido-4-O-benzyl-5-deoxy-1,2-O-isopropylidene-β-D-psicopyranose (872345-45-4) + benzyl bromide (100-39-0) → 5-azido-3,4-di-O-benzyl-5-deoxy-1,2-O-isopropylidene-β-D-psicopyranose (872345-46-5)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; at 20 ℃; for 2h;

DOI:10.1016/j.tet.2005.09.043

Reference yield:

(5S,8R,9R)-8-Azido-9-benzyloxy-2,2-dimethyl-1,3,6-trioxa-spiro[4.5]decan-10-one (872345-44-3) → 5-azido-3,4-di-O-benzyl-5-deoxy-1,2-O-isopropylidene-β-D-psicopyranose (872345-46-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 88 percent / NaBH₄ / methanol / 1 h / cooling

2: 72 percent / NaH / dimethylformamide / 2 h / 20 °C

With sodium tetrahydroborate; sodium hydride; In methanol; N,N-dimethyl-formamide;

DOI:10.1016/j.tet.2005.09.043

Reference yield:

5-azido-4-O-benzyl-5-deoxy-1,2-O-isopropylidene-β-D-fructopyranose (872345-43-2) → 5-azido-3,4-di-O-benzyl-5-deoxy-1,2-O-isopropylidene-β-D-psicopyranose (872345-46-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 93.4 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h / 20 °C

2: 88 percent / NaBH₄ / methanol / 1 h / cooling

3: 72 percent / NaH / dimethylformamide / 2 h / 20 °C

With sodium tetrahydroborate; sodium hydride; Dess-Martin periodane; In methanol; dichloromethane; N,N-dimethyl-formamide; 1: Dess-Martin oxidation;

DOI:10.1016/j.tet.2005.09.043

upstream raw materials:

5-azido-4-O-benzyl-5-deoxy-1,2-O-isopropylidene-β-D-psicopyranose

benzyl bromide

(5S,8R,9R)-8-Azido-9-benzyloxy-2,2-dimethyl-1,3,6-trioxa-spiro[4.5]decan-10-one

5-azido-4-O-benzyl-5-deoxy-1,2-O-isopropylidene-β-D-fructopyranose

Downstream raw materials:

(3S,4R,5R)-3,4-dibenzyloxy-2',5'-di-O-tert-butyldiphenylsilyl-2,5-bis(hydroxymethyl)-δ²-pyrroline

(2R,3R,4S,5S)-3,4-dibenzyloxy-2',5'-di-O-tert-butyldiphenylsilyl-2,5-bis(hydroxymethyl)-δ²-pyrrolidine

5-azido-3,4-di-O-benzyl-1-O-tert-butyldiphenylsilyl-5-deoxy-α-D-psicopyranose

5-azido-3,4-di-O-benzyl-1,6-di-O-tert-butyldiphenylsilyl-5-deoxy-D-psicose