(1R,2S,2'S,3S,4R,6S)-4-acetoxy-1-(2'-benzyloxycarbonylamino-3'-tert-butyldiphenylsilyloxy-propyl)-2,3-epoxy-6-hydroxy-2-cyclohexen-1-ol

Base Information

Chemical Name:(1R,2S,2'S,3S,4R,6S)-4-acetoxy-1-(2'-benzyloxycarbonylamino-3'-tert-butyldiphenylsilyloxy-propyl)-2,3-epoxy-6-hydroxy-2-cyclohexen-1-ol
CAS No.:942618-49-7
Molecular Formula:C₃₅H₄₃NO₈Si
Molecular Weight:633.814
Hs Code.:

Synonyms:(1R,2S,2'S,3S,4R,6S)-4-acetoxy-1-(2'-benzyloxycarbonylamino-3'-tert-butyldiphenylsilyloxy-propyl)-2,3-epoxy-6-hydroxy-2-cyclohexen-1-ol

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Chemical Property of (1R,2S,2'S,3S,4R,6S)-4-acetoxy-1-(2'-benzyloxycarbonylamino-3'-tert-butyldiphenylsilyloxy-propyl)-2,3-epoxy-6-hydroxy-2-cyclohexen-1-ol

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Technology Process of (1R,2S,2'S,3S,4R,6S)-4-acetoxy-1-(2'-benzyloxycarbonylamino-3'-tert-butyldiphenylsilyloxy-propyl)-2,3-epoxy-6-hydroxy-2-cyclohexen-1-ol

There total 12 articles about (1R,2S,2'S,3S,4R,6S)-4-acetoxy-1-(2'-benzyloxycarbonylamino-3'-tert-butyldiphenylsilyloxy-propyl)-2,3-epoxy-6-hydroxy-2-cyclohexen-1-ol 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: 84.0%

: 942618-48-6
(1S,2'S,4R,6S)-4-acetoxy-1-(2'-benzyloxycarbonylamino-3'-tert-butyldiphenylsilyloxy-propyl)-6-hydroxy-2-cyclohexen-1-ol

: 942618-49-7
(1R,2S,2'S,3S,4R,6S)-4-acetoxy-1-(2'-benzyloxycarbonylamino-3'-tert-butyldiphenylsilyloxy-propyl)-2,3-epoxy-6-hydroxy-2-cyclohexen-1-ol

: C₃₅H₄₅NO₉Si

Guidance literature:: With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 ℃; for 70h;
DOI:10.1021/jo070337k

Reference yield:

: 942618-32-8
(3S,5S,10S)-3-benzyloxycarbonylamino-10-triethylsilyloxy-1-oxaspiro[4,5]dec-6-ene-2,8-dione

: 942618-49-7
(1R,2S,2'S,3S,4R,6S)-4-acetoxy-1-(2'-benzyloxycarbonylamino-3'-tert-butyldiphenylsilyloxy-propyl)-2,3-epoxy-6-hydroxy-2-cyclohexen-1-ol

Guidance literature:: Multi-step reaction with 7 steps

1: 95 percent / NaBH₄; CeCl₃*7H₂O / propan-2-ol; tetrahydrofuran / 0.67 h / 0 °C

2: 99 percent / mCPBA / CH₂Cl₂ / 24 h / 20 °C

3: 99 percent / pyridine; DMAP / CH₂Cl₂ / 24 h / 0 - 20 °C

4: 94 percent / NaBH₄ / ethanol / 9 h / 0 °C

5: 94 percent / TBAF / tetrahydrofuran / 0.17 h / 20 °C

6: 83 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

7: 84 percent / mCPBA / CH₂Cl₂ / 70 h / 0 °C

With pyridine; 2,6-dimethylpyridine; dmap; sodium tetrahydroborate; cerium(III) chloride; tetrabutyl ammonium fluoride; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; ethanol; dichloromethane; isopropyl alcohol;
DOI:10.1021/jo070337k

Reference yield:

: 942618-33-9
(3S,5S,8R,10S)-3-benzyloxycarbonylamino-8-hydroxy-10-triethylsilyloxy-1-oxaspiro[4,5]dec-6-en-2-one

: 942618-49-7
(1R,2S,2'S,3S,4R,6S)-4-acetoxy-1-(2'-benzyloxycarbonylamino-3'-tert-butyldiphenylsilyloxy-propyl)-2,3-epoxy-6-hydroxy-2-cyclohexen-1-ol

Guidance literature:: Multi-step reaction with 6 steps

1: 99 percent / mCPBA / CH₂Cl₂ / 24 h / 20 °C

2: 99 percent / pyridine; DMAP / CH₂Cl₂ / 24 h / 0 - 20 °C

3: 94 percent / NaBH₄ / ethanol / 9 h / 0 °C

4: 94 percent / TBAF / tetrahydrofuran / 0.17 h / 20 °C

5: 83 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

6: 84 percent / mCPBA / CH₂Cl₂ / 70 h / 0 °C

With pyridine; 2,6-dimethylpyridine; dmap; sodium tetrahydroborate; tetrabutyl ammonium fluoride; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; ethanol; dichloromethane;
DOI:10.1021/jo070337k