(3R,4S,5S,6R)-1-azido-3,4-dibenzyloxy-7-(tert-butyldiphenylsilyloxy)-5,6-(cyclopentylidenedioxy)heptan-2-one

Base Information

Chemical Name:(3R,4S,5S,6R)-1-azido-3,4-dibenzyloxy-7-(tert-butyldiphenylsilyloxy)-5,6-(cyclopentylidenedioxy)heptan-2-one
CAS No.:898801-54-2
Molecular Formula:C₄₂H₄₉N₃O₆Si
Molecular Weight:719.953
Hs Code.:

Synonyms:(3R,4S,5S,6R)-1-azido-3,4-dibenzyloxy-7-(tert-butyldiphenylsilyloxy)-5,6-(cyclopentylidenedioxy)heptan-2-one

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Chemical Property of (3R,4S,5S,6R)-1-azido-3,4-dibenzyloxy-7-(tert-butyldiphenylsilyloxy)-5,6-(cyclopentylidenedioxy)heptan-2-one

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Technology Process of (3R,4S,5S,6R)-1-azido-3,4-dibenzyloxy-7-(tert-butyldiphenylsilyloxy)-5,6-(cyclopentylidenedioxy)heptan-2-one

There total 11 articles about (3R,4S,5S,6R)-1-azido-3,4-dibenzyloxy-7-(tert-butyldiphenylsilyloxy)-5,6-(cyclopentylidenedioxy)heptan-2-one 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: 83.0%

: 898801-60-0
(3S,4R,5S,6R)-1-azido-3,4-dibenzyloxy-7-(tert-butyldiphenylsilyloxy)-5,6-(cyclopentylidenedioxy)heptan-2-ol

: 898801-54-2
(3R,4S,5S,6R)-1-azido-3,4-dibenzyloxy-7-(tert-butyldiphenylsilyloxy)-5,6-(cyclopentylidenedioxy)heptan-2-one

Guidance literature:: With oxalyl dichloride; TEA; dimethyl sulfoxide; In dichloromethane; at -60 - 20 ℃; for 1.5h;
DOI:10.1055/s-2006-939693

Reference yield:

: 898801-57-5
(2R,3S,4S,5S)-4,5-dibenzyloxyhept-6-en-1,2,3-triol

: 898801-54-2
(3R,4S,5S,6R)-1-azido-3,4-dibenzyloxy-7-(tert-butyldiphenylsilyloxy)-5,6-(cyclopentylidenedioxy)heptan-2-one

Guidance literature:: Multi-step reaction with 5 steps

1: 83 percent / TEA; DMAP / CH₂Cl₂ / 72 h / 0 - 20 °C

2: 93 percent / CSA / methanol / 0.42 h / 20 °C

3: 87 percent / MCPBA / CH₂Cl₂ / 60 h / 0 - 20 °C

4: 94 percent / NaN₃; NH₄Cl / ethanol / 45 h / 78 °C

5: 83 percent / (COCl)2; DMSO; TEA / CH₂Cl₂ / 1.5 h / -60 - 20 °C

With dmap; sodium azide; oxalyl dichloride; TEA; camphor-10-sulfonic acid; ammonium chloride; dimethyl sulfoxide; 3-chloro-benzenecarboperoxoic acid; In methanol; ethanol; dichloromethane; 5: Swern oxidation;
DOI:10.1055/s-2006-939693

Reference yield:

: 958265-80-0
(2R,3S,4R,5S)-4,5-di-O-benzyl-1,3-O-benzylidenehept-6-ene-1,2,3,4,5-pentaol

: 898801-54-2
(3R,4S,5S,6R)-1-azido-3,4-dibenzyloxy-7-(tert-butyldiphenylsilyloxy)-5,6-(cyclopentylidenedioxy)heptan-2-one

Guidance literature:: Multi-step reaction with 6 steps

1: 97 percent / CSA; 1,3-propanedithiol / methanol / 15 h / 20 °C

2: 83 percent / TEA; DMAP / CH₂Cl₂ / 72 h / 0 - 20 °C

3: 93 percent / CSA / methanol / 0.42 h / 20 °C

4: 87 percent / MCPBA / CH₂Cl₂ / 60 h / 0 - 20 °C

5: 94 percent / NaN₃; NH₄Cl / ethanol / 45 h / 78 °C

6: 83 percent / (COCl)2; DMSO; TEA / CH₂Cl₂ / 1.5 h / -60 - 20 °C

With 1.3-propanedithiol; dmap; sodium azide; oxalyl dichloride; TEA; camphor-10-sulfonic acid; ammonium chloride; dimethyl sulfoxide; 3-chloro-benzenecarboperoxoic acid; In methanol; ethanol; dichloromethane; 6: Swern oxidation;
DOI:10.1055/s-2006-939693