(2S,3S)-(3-[(2R,7S,E)-9-tert-butyldiphenylsilyl-oxy-2,6,7-trimethyl-4-methylenenon-5-enyl]oxiran-2-yl)methanol

Base Information

Chemical Name:(2S,3S)-(3-[(2R,7S,E)-9-tert-butyldiphenylsilyl-oxy-2,6,7-trimethyl-4-methylenenon-5-enyl]oxiran-2-yl)methanol
CAS No.:1006725-06-9
Molecular Formula:C₃₂H₄₆O₃Si
Molecular Weight:506.801
Hs Code.:

Synonyms:(2S,3S)-(3-[(2R,7S,E)-9-tert-butyldiphenylsilyl-oxy-2,6,7-trimethyl-4-methylenenon-5-enyl]oxiran-2-yl)methanol

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Chemical Property of (2S,3S)-(3-[(2R,7S,E)-9-tert-butyldiphenylsilyl-oxy-2,6,7-trimethyl-4-methylenenon-5-enyl]oxiran-2-yl)methanol

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Technology Process of (2S,3S)-(3-[(2R,7S,E)-9-tert-butyldiphenylsilyl-oxy-2,6,7-trimethyl-4-methylenenon-5-enyl]oxiran-2-yl)methanol

There total 5 articles about (2S,3S)-(3-[(2R,7S,E)-9-tert-butyldiphenylsilyl-oxy-2,6,7-trimethyl-4-methylenenon-5-enyl]oxiran-2-yl)methanol 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: 61.0%

: C₂₃H₃₁IOSi

: 309241-42-7
(2S,3S)-3-[(S)-2-(methyl-4-(trimethylstannyl) pent-4-enyl)oxiran-2-yl]methanol

: 1006725-06-9
(2S,3S)-(3-[(2R,7S,E)-9-tert-butyldiphenylsilyl-oxy-2,6,7-trimethyl-4-methylenenon-5-enyl]oxiran-2-yl)methanol

Guidance literature:: (2S,3S)-3-[(S)-2-(methyl-4-(trimethylstannyl) pent-4-enyl)oxiran-2-yl]methanol; With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; triphenyl-arsane; In 1-methyl-pyrrolidin-2-one; at 20 ℃; for 0.25h; Inert atmosphere;

C₂₃H₃₁IOSi; With copper(I) thiophene-2-carboxylate; In 1-methyl-pyrrolidin-2-one; at 35 ℃; for 0.666667h; Inert atmosphere;
DOI:10.1016/j.tet.2013.02.062

Reference yield:

: 1006724-80-6
C₂₃H₃₁IOSi

: 309241-57-4
tert-Butyl-dimethyl-[(2S,3S)-3-((R)-2-methyl-pent-4-ynyl)-oxiranylmethoxy]-silane

: 1006725-06-9
(2S,3S)-(3-[(2R,7S,E)-9-tert-butyldiphenylsilyl-oxy-2,6,7-trimethyl-4-methylenenon-5-enyl]oxiran-2-yl)methanol

Guidance literature:: tert-Butyl-dimethyl-[(2S,3S)-3-((R)-2-methyl-pent-4-ynyl)-oxiranylmethoxy]-silane; With trimethylsilyltributyltin; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In N,N-dimethyl-formamide;

With tetrabutyl ammonium fluoride; In dimethyl sulfoxide; at 80 ℃;

C₂₃H₃₁IOSi; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In N,N-dimethyl-formamide; at 20 ℃; Further stages.;
DOI:10.1002/anie.200704024

Reference yield:

: 1427556-22-6
tert-butyl (2S,3S)-3-[(R)-2-methylpent-4-ynyl] oxiran-2-ylmethoxy diphenylsilane

: 1006725-06-9
(2S,3S)-(3-[(2R,7S,E)-9-tert-butyldiphenylsilyl-oxy-2,6,7-trimethyl-4-methylenenon-5-enyl]oxiran-2-yl)methanol

Guidance literature:: Multi-step reaction with 3 steps

1.1: palladium diacetate; triphenylphosphine / 1,2-dimethoxyethane / 168 h / 35 °C / Inert atmosphere

2.1: tetrabutyl ammonium fluoride / tetrahydrofuran; dimethyl sulfoxide / 0.5 h / 20 - 80 °C / Inert atmosphere

3.1: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; triphenyl-arsane / 1-methyl-pyrrolidin-2-one / 0.25 h / 20 °C / Inert atmosphere

3.2: 0.67 h / 35 °C / Inert atmosphere

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; triphenyl-arsane; tetrabutyl ammonium fluoride; palladium diacetate; triphenylphosphine; In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; 1,2-dimethoxyethane; dimethyl sulfoxide; 3.1: |Stille Cross Coupling / 3.2: |Stille Cross Coupling;
DOI:10.1016/j.tet.2013.02.062