(E)-(4R,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-4-methyl-hex-2-enoic acid benzyl ester

Base Information

Chemical Name:(E)-(4R,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-4-methyl-hex-2-enoic acid benzyl ester
CAS No.:206762-57-4
Molecular Formula:C₂₀H₃₂O₃Si
Molecular Weight:348.558
Hs Code.:

Synonyms:(E)-(4R,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-4-methyl-hex-2-enoic acid benzyl ester

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Chemical Property of (E)-(4R,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-4-methyl-hex-2-enoic acid benzyl ester

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Technology Process of (E)-(4R,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-4-methyl-hex-2-enoic acid benzyl ester

There total 6 articles about (E)-(4R,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-4-methyl-hex-2-enoic acid benzyl ester 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:

: 69739-34-0
t-butyldimethylsiyl triflate

: 206762-51-8
(R,R)-2-[(E)-(benzyloxycarbonyl)vinyl]-2,3-dimethyloxirane

: 206762-57-4
(E)-(4R,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-4-methyl-hex-2-enoic acid benzyl ester

: (E)-(4S,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-4-methyl-hex-2-enoic acid benzyl ester

Guidance literature:: (R,R)-2-[(E)-(benzyloxycarbonyl)vinyl]-2,3-dimethyloxirane; With formic acid; tributylphosphine; triethylamine; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; In 1,4-dioxane; at 20 ℃; for 9.5h;

t-butyldimethylsiyl triflate; With 2,6-dimethylpyridine; In dichloromethane; at 0 ℃; for 3h; Title compound not separated from byproducts;
DOI:10.1021/jo9805246

Reference yield:

: 497-02-9
(E)-2-methyl-2-buten-1-ol

: 206762-57-4
(E)-(4R,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-4-methyl-hex-2-enoic acid benzyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: diisopropyl D-tartrate; 3-Angstroem molecular sieves; cumene hydroperoxide / titanium(IV) isopropoxide / CH₂Cl₂ / 13 h / -78 - -70 °C

2.1: 4-Angstroem molecular sieves; 4-methylmorpholine N-oxide / tetrapropylammonium perruthenate / acetonitrile / 1 h / 20 °C

3.1: LiCl; i-Pr₂NEt / acetonitrile / 1 h / 0 °C

4.1: Bu₃P; Et₃N; HCO₂H / tris(dibenzylideneacetone)dipalladium⁽⁰⁾-chloroform adduct / dioxane / 9.5 h / 20 °C

4.2: 2,6-lutidine / CH₂Cl₂ / 3 h / 0 °C

With formic acid; tributylphosphine; Cumene hydroperoxide; 3 A molecular sieve; 4 A molecular sieve; D-(-)-diisopropyl tartrate; 4-methylmorpholine N-oxide; triethylamine; N-ethyl-N,N-diisopropylamine; lithium chloride; titanium(IV) isopropylate; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; tetrapropylammonium perruthennate; In 1,4-dioxane; dichloromethane; acetonitrile; 1.1: Sharpless epoxidation / 2.1: Oxidation / 3.1: Masamune-Roush olefination / 4.1: Catalytic hydrogenation / 4.2: silylation;
DOI:10.1021/jo9805246

Reference yield:

: 7396-44-3
benzyl diethylphosphonoacetate

: 206762-57-4
(E)-(4R,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-4-methyl-hex-2-enoic acid benzyl ester

Guidance literature:: Multi-step reaction with 2 steps

1.1: LiCl; i-Pr₂NEt / acetonitrile / 1 h / 0 °C

2.1: Bu₃P; Et₃N; HCO₂H / tris(dibenzylideneacetone)dipalladium⁽⁰⁾-chloroform adduct / dioxane / 9.5 h / 20 °C

2.2: 2,6-lutidine / CH₂Cl₂ / 3 h / 0 °C

With formic acid; tributylphosphine; triethylamine; N-ethyl-N,N-diisopropylamine; lithium chloride; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; In 1,4-dioxane; acetonitrile; 1.1: Masamune-Roush olefination / 2.1: Catalytic hydrogenation / 2.2: silylation;
DOI:10.1021/jo9805246