(3S,4S,5S)-4-acetoxy-5-azido-3-(tert-butyldiphenylsilyloxy)cyclo-hex-1-enylmethyl acetate

Base Information

Chemical Name:(3S,4S,5S)-4-acetoxy-5-azido-3-(tert-butyldiphenylsilyloxy)cyclo-hex-1-enylmethyl acetate
CAS No.:1476028-75-7
Molecular Formula:C₂₇H₃₃N₃O₅Si
Molecular Weight:507.662
Hs Code.:

Synonyms:(3S,4S,5S)-4-acetoxy-5-azido-3-(tert-butyldiphenylsilyloxy)cyclo-hex-1-enylmethyl acetate

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Chemical Property of (3S,4S,5S)-4-acetoxy-5-azido-3-(tert-butyldiphenylsilyloxy)cyclo-hex-1-enylmethyl acetate

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Technology Process of (3S,4S,5S)-4-acetoxy-5-azido-3-(tert-butyldiphenylsilyloxy)cyclo-hex-1-enylmethyl acetate

There total 8 articles about (3S,4S,5S)-4-acetoxy-5-azido-3-(tert-butyldiphenylsilyloxy)cyclo-hex-1-enylmethyl acetate 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:

: C₂₃H₂₉N₃O₃Si

: 108-24-7
acetic anhydride

: 1476028-75-7
(3S,4S,5S)-4-acetoxy-5-azido-3-(tert-butyldiphenylsilyloxy)cyclo-hex-1-enylmethyl acetate

Guidance literature:: With dmap; triethylamine; In ethyl acetate; at 0 ℃; for 1h;
DOI:10.1002/ejoc.201300804

Reference yield:

: 1476028-71-3
(3S,4S,5S)-ethyl 5-azido-3,4-dihydroxycyclohex-1-ene-1-carboxylate

: 1476028-75-7
(3S,4S,5S)-4-acetoxy-5-azido-3-(tert-butyldiphenylsilyloxy)cyclo-hex-1-enylmethyl acetate

Guidance literature:: Multi-step reaction with 3 steps

1: dmap; triethylamine / dichloromethane / 5 h / 20 °C

2: diisobutylaluminium hydride / dichloromethane; hexane / 1 h / -10 °C

3: dmap; triethylamine / ethyl acetate / 1 h / 0 °C

With dmap; diisobutylaluminium hydride; triethylamine; In hexane; dichloromethane; ethyl acetate;
DOI:10.1002/ejoc.201300804

Reference yield:

: 1476028-70-2
(3S,4R,5R)-5-methanesulfonyloxy-3,4-dihydroxy-1-cyclohexene-1-carboxylic acid ethyl ester

: 1476028-75-7
(3S,4S,5S)-4-acetoxy-5-azido-3-(tert-butyldiphenylsilyloxy)cyclo-hex-1-enylmethyl acetate

Guidance literature:: Multi-step reaction with 4 steps

1: sodium azide; acetic acid / dimethyl sulfoxide / 2 h / 85 °C

2: dmap; triethylamine / dichloromethane / 5 h / 20 °C

3: diisobutylaluminium hydride / dichloromethane; hexane / 1 h / -10 °C

4: dmap; triethylamine / ethyl acetate / 1 h / 0 °C

With dmap; sodium azide; diisobutylaluminium hydride; acetic acid; triethylamine; In hexane; dichloromethane; dimethyl sulfoxide; ethyl acetate;
DOI:10.1002/ejoc.201300804