tert-Butyl-dimethyl-[(2R,4S,5R)-2-phenyl-4-((2R,3R)-3-vinyl-oxiranylmethyl)-[1,3]dioxan-5-yloxy]-silane

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Chemical Name:tert-Butyl-dimethyl-[(2R,4S,5R)-2-phenyl-4-((2R,3R)-3-vinyl-oxiranylmethyl)-[1,3]dioxan-5-yloxy]-silane
CAS No.:315204-12-7
Molecular Formula:C₂₁H₃₂O₄Si
Molecular Weight:376.568
Hs Code.:

Synonyms:tert-Butyl-dimethyl-[(2R,4S,5R)-2-phenyl-4-((2R,3R)-3-vinyl-oxiranylmethyl)-[1,3]dioxan-5-yloxy]-silane

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Chemical Property of tert-Butyl-dimethyl-[(2R,4S,5R)-2-phenyl-4-((2R,3R)-3-vinyl-oxiranylmethyl)-[1,3]dioxan-5-yloxy]-silane

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Technology Process of tert-Butyl-dimethyl-[(2R,4S,5R)-2-phenyl-4-((2R,3R)-3-vinyl-oxiranylmethyl)-[1,3]dioxan-5-yloxy]-silane

There total 10 articles about tert-Butyl-dimethyl-[(2R,4S,5R)-2-phenyl-4-((2R,3R)-3-vinyl-oxiranylmethyl)-[1,3]dioxan-5-yloxy]-silane 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:

: 213815-23-7
(E)-4-[(2R,4S,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-2-phenyl-[1,3]dioxan-4-yl]-but-2-enoic acid methyl ester

: 315204-12-7
tert-Butyl-dimethyl-[(2R,4S,5R)-2-phenyl-4-((2R,3R)-3-vinyl-oxiranylmethyl)-[1,3]dioxan-5-yloxy]-silane

Guidance literature:: Multi-step reaction with 4 steps

1: 7.34 g / DIBALH / CH₂Cl₂; toluene / 2 h / -78 °C

2: 87 percent / (-)-diethyl tartrate; titanium(IV) isopropoxide; tert-butyl hydroperoxide / molecular sieves 4A / CH₂Cl₂; 2,2,4-trimethyl-pentane / -20 - 20 °C

3: triethylamine; SO₃*pyridine / CH₂Cl₂; dimethylsulfoxide / 0.5 h / 0 °C

4: 5.38 g / tetrahydrofuran / 0.5 h / 0 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; pyridine-SO₃ complex; diisobutylaluminium hydride; (-)-diethyl tartrate; triethylamine; 4 A molecular sieve; In tetrahydrofuran; 2,2,4-trimethylpentane; dichloromethane; dimethyl sulfoxide; toluene; 2: Sharpless asymmetric epoxidation / 4: Wittig methylenation;
DOI:10.1016/S0040-4020(01)00164-8

Reference yield:

: 315204-07-0
(E)-4-[(2R,4S,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-2-phenyl-[1,3]dioxan-4-yl]-but-2-en-1-ol

: 315204-12-7
tert-Butyl-dimethyl-[(2R,4S,5R)-2-phenyl-4-((2R,3R)-3-vinyl-oxiranylmethyl)-[1,3]dioxan-5-yloxy]-silane

Guidance literature:: Multi-step reaction with 3 steps

1: 87 percent / (-)-diethyl tartrate; titanium(IV) isopropoxide; tert-butyl hydroperoxide / molecular sieves 4A / CH₂Cl₂; 2,2,4-trimethyl-pentane / -20 - 20 °C

2: triethylamine; SO₃*pyridine / CH₂Cl₂; dimethylsulfoxide / 0.5 h / 0 °C

3: 5.38 g / tetrahydrofuran / 0.5 h / 0 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; pyridine-SO₃ complex; (-)-diethyl tartrate; triethylamine; 4 A molecular sieve; In tetrahydrofuran; 2,2,4-trimethylpentane; dichloromethane; dimethyl sulfoxide; 1: Sharpless asymmetric epoxidation / 3: Wittig methylenation;
DOI:10.1016/S0040-4020(01)00164-8

Reference yield:

: 315204-08-1
((2R,3R)-3-(((2R,4S,5R)-5-(tert-butyldimethylsilyloxy)-2-phenyl-1,3-dioxan-4-yl)methyl)oxiran-2-yl)methanol

: 315204-12-7
tert-Butyl-dimethyl-[(2R,4S,5R)-2-phenyl-4-((2R,3R)-3-vinyl-oxiranylmethyl)-[1,3]dioxan-5-yloxy]-silane

Guidance literature:: Multi-step reaction with 2 steps

1: triethylamine; SO₃*pyridine / CH₂Cl₂; dimethylsulfoxide / 0.5 h / 0 °C

2: 5.38 g / tetrahydrofuran / 0.5 h / 0 °C

With pyridine-SO₃ complex; triethylamine; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; 2: Wittig methylenation;
DOI:10.1016/S0040-4020(01)00164-8