(1R,3S,4S,5R,6S,8R,9R)-4-azido-3,5-bis(benzyloxy)-8,9-isopropylidenedioxy-7-oxabicyclo<4.3.0>nonane

Base Information

• Chemical Name: (1R,3S,4S,5R,6S,8R,9R)-4-azido-3,5-bis(benzyloxy)-8,9-isopropylidenedioxy-7-oxabicyclo<4.3.0>nonane
• CAS No.: 112473-51-5
• Molecular Formula: C₂₅H₂₉N₃O₅
• Molecular Weight: 451.522
• Mol file: 112473-51-5.mol

Synonyms:(1R,3S,4S,5R,6S,8R,9R)-4-azido-3,5-bis(benzyloxy)-8,9-isopropylidenedioxy-7-oxabicyclo<4.3.0>nonane

Chemical Property of (1R,3S,4S,5R,6S,8R,9R)-4-azido-3,5-bis(benzyloxy)-8,9-isopropylidenedioxy-7-oxabicyclo<4.3.0>nonane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,3S,4S,5R,6S,8R,9R)-4-azido-3,5-bis(benzyloxy)-8,9-isopropylidenedioxy-7-oxabicyclo<4.3.0>nonane

There total 3 articles about (1R,3S,4S,5R,6S,8R,9R)-4-azido-3,5-bis(benzyloxy)-8,9-isopropylidenedioxy-7-oxabicyclo<4.3.0>nonane 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: 82.0%

benzyl bromide (100-39-0) + (1R,3S,4S,5R,6S,8R,9R)-4-azido-8,9-isopropylidenedioxy-7-oxabicyclo<4.3.0>nonane-3,5-diol (112473-49-1) → (1R,3S,4S,5R,6S,8R,9R)-4-azido-3,5-bis(benzyloxy)-8,9-isopropylidenedioxy-7-oxabicyclo<4.3.0>nonane (112473-51-5)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; 1.) 20 min; 2.) r.t., 5 h;

DOI:10.1246/bcsj.60.1727

Reference yield:

(1R,4S,5S,6S,8R,9R)-4,5-epoxy-8,9-isopropylidenedioxy-7-oxabicyclo<4.3.0>nonan-3-one (102562-01-6) → (1R,3S,4S,5R,6S,8R,9R)-4-azido-3,5-bis(benzyloxy)-8,9-isopropylidenedioxy-7-oxabicyclo<4.3.0>nonane (112473-51-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 70 percent / NaBH₄ / ethanol / 0.67 h / 0 °C

2: 84 percent / NaN₃, NH₄Cl / 2-methoxy-ethanol; H₂O / 4 h / Heating

3: 82 percent / 1.) NaH / dimethylformamide / 1.) 20 min; 2.) r.t., 5 h

With sodium tetrahydroborate; sodium azide; sodium hydride; ammonium chloride; In ethanol; 2-methoxy-ethanol; water; N,N-dimethyl-formamide;

DOI:10.1246/bcsj.60.1727

Reference yield:

(1R,3S,4R,5S,6S,8R,9R)-4,5-epoxy-8,9-isopropylidenedioxy-7-oxabicyclo<4.3.0>nonan-3-ol (102562-02-7,102629-08-3,115184-66-2) → (1R,3S,4S,5R,6S,8R,9R)-4-azido-3,5-bis(benzyloxy)-8,9-isopropylidenedioxy-7-oxabicyclo<4.3.0>nonane (112473-51-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 84 percent / NaN₃, NH₄Cl / 2-methoxy-ethanol; H₂O / 4 h / Heating

2: 82 percent / 1.) NaH / dimethylformamide / 1.) 20 min; 2.) r.t., 5 h

With sodium azide; sodium hydride; ammonium chloride; In 2-methoxy-ethanol; water; N,N-dimethyl-formamide;

DOI:10.1246/bcsj.60.1727

upstream raw materials:

benzyl bromide

(1R,3S,4S,5R,6S,8R,9R)-4-azido-8,9-isopropylidenedioxy-7-oxabicyclo<4.3.0>nonane-3,5-diol

(1R,3S,4R,5S,6S,8R,9R)-4,5-epoxy-8,9-isopropylidenedioxy-7-oxabicyclo<4.3.0>nonan-3-ol

(1R,4S,5S,6S,8R,9R)-4,5-epoxy-8,9-isopropylidenedioxy-7-oxabicyclo<4.3.0>nonan-3-one

Downstream raw materials:

(2S,3R,3aS,5S,6S,7R,7aS)-6-Azido-5,7-bis-benzyloxy-octahydro-benzofuran-2,3-diol

(3S,4S,5S)-4-azido-3,5-bis(benzyloxy)-1-cyclohexene-1-methanol