(Z,2R,3R,8R,9S)-8-tert-butyldiphenylsilanyloxy-9-ethyl-3-hydroxy-2-hydroxymethyl-2,3,4,7,8,9-hexahydrooxonine

Base Information

Chemical Name:(Z,2R,3R,8R,9S)-8-tert-butyldiphenylsilanyloxy-9-ethyl-3-hydroxy-2-hydroxymethyl-2,3,4,7,8,9-hexahydrooxonine
CAS No.:140225-14-5
Molecular Formula:C₂₇H₃₈O₄Si
Molecular Weight:454.682
Hs Code.:

Synonyms:(Z,2R,3R,8R,9S)-8-tert-butyldiphenylsilanyloxy-9-ethyl-3-hydroxy-2-hydroxymethyl-2,3,4,7,8,9-hexahydrooxonine

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Chemical Property of (Z,2R,3R,8R,9S)-8-tert-butyldiphenylsilanyloxy-9-ethyl-3-hydroxy-2-hydroxymethyl-2,3,4,7,8,9-hexahydrooxonine

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Technology Process of (Z,2R,3R,8R,9S)-8-tert-butyldiphenylsilanyloxy-9-ethyl-3-hydroxy-2-hydroxymethyl-2,3,4,7,8,9-hexahydrooxonine

There total 19 articles about (Z,2R,3R,8R,9S)-8-tert-butyldiphenylsilanyloxy-9-ethyl-3-hydroxy-2-hydroxymethyl-2,3,4,7,8,9-hexahydrooxonine 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%

: 140170-11-2
(Z,2S,3R,8R)-3-tert-butyldiphenylsilanyloxy-8-dimethylsilanyloxy-2-ethyl-9-methylene-2,3,4,7,8,9-hexahydrooxonine

: 140170-15-6
(Z,2S,3R,8R,9S)-8-tert-butyldiphenylsilanyloxy-9-ethyl-3-hydroxy-2-hydroxymethyl-2,3,4,7,8,9-hexahydrooxonine

: 140225-14-5
(Z,2R,3R,8R,9S)-8-tert-butyldiphenylsilanyloxy-9-ethyl-3-hydroxy-2-hydroxymethyl-2,3,4,7,8,9-hexahydrooxonine

Guidance literature:: (Z,2S,3R,8R)-3-tert-butyldiphenylsilanyloxy-8-dimethylsilanyloxy-2-ethyl-9-methylene-2,3,4,7,8,9-hexahydrooxonine; With Wilkinson's catalyst; triphenylphosphine; In tetrahydrofuran; for 16h; Reflux;

With potassium hydroxide; water; dihydrogen peroxide; In tetrahydrofuran; methanol; at 20 ℃; for 1.5h; diastereoselective reaction;
DOI:10.1002/chem.200701567

Reference yield:

: 140170-12-3
(Z,3R,8R,9S)-8-tert-butyldiphenylsilanyloxy-9-ethyl-3-hydroxy-2-methylene-2,3,4,7,8,9-hexahydrooxonine

: 140170-15-6,140225-14-5
(+/-)-(Z,2R,3R,8R,9S)-8-tert-butyldiphenylsilanyloxy-9-ethyl-3-hydroxy-2-hydroxymethyl-2,3,4,7,8,9-hexahydrooxonine

Guidance literature:: Multi-step reaction with 2 steps

1: 100 percent / NH₄Cl / 60 °C

With ammonium chloride;
DOI:10.1016/S0040-4039(00)92339-6

Reference yield:

: 140170-12-3
(Z,3R,8R,9S)-8-tert-butyldiphenylsilanyloxy-9-ethyl-3-hydroxy-2-methylene-2,3,4,7,8,9-hexahydrooxonine

: 140170-15-6,140225-14-5
(Z)-(2S,3R,8R,9S)-8-(tert-Butyl-diphenyl-silanyloxy)-9-ethyl-2-hydroxymethyl-2,3,4,7,8,9-hexahydro-oxonin-3-ol

Guidance literature:: Multi-step reaction with 2 steps

1: 100 percent / NH₄Cl / 60 °C

With ammonium chloride;
DOI:10.1016/S0040-4039(00)92339-6