methyl (4R)-2-hydroxy-2-(2-hydroxy-2-phenylethyl)-4-methyl-4-vinyltetrahydrofuran-3-carboxylate

Base Information

Chemical Name:methyl (4R)-2-hydroxy-2-(2-hydroxy-2-phenylethyl)-4-methyl-4-vinyltetrahydrofuran-3-carboxylate
CAS No.:1289155-41-4
Molecular Formula:C₁₇H₂₂O₅
Molecular Weight:306.359
Hs Code.:

Synonyms:methyl (4R)-2-hydroxy-2-(2-hydroxy-2-phenylethyl)-4-methyl-4-vinyltetrahydrofuran-3-carboxylate

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Chemical Property of methyl (4R)-2-hydroxy-2-(2-hydroxy-2-phenylethyl)-4-methyl-4-vinyltetrahydrofuran-3-carboxylate

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Technology Process of methyl (4R)-2-hydroxy-2-(2-hydroxy-2-phenylethyl)-4-methyl-4-vinyltetrahydrofuran-3-carboxylate

There total 4 articles about methyl (4R)-2-hydroxy-2-(2-hydroxy-2-phenylethyl)-4-methyl-4-vinyltetrahydrofuran-3-carboxylate 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: 49.0%

: 53063-63-1
5-hydroxy-3-oxo-5-phenyl-valeric acid methyl ester

: 1838-94-4
isoprene epoxide

: 1287701-97-6
C₁₇H₂₂O₅

: 1289155-41-4
methyl (4R)-2-hydroxy-2-(2-hydroxy-2-phenylethyl)-4-methyl-4-vinyltetrahydrofuran-3-carboxylate

Guidance literature:: 5-hydroxy-3-oxo-5-phenyl-valeric acid methyl ester; With tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; (1R,2R)-(+)-1,2-diaminocyclohexane-N,N’-bis(2-diphenylphosphino-1-naphthoyl); In dichloromethane; at 20 ℃; Inert atmosphere;

isoprene epoxide; In dichloromethane; at 20 ℃; for 0.5h; optical yield given as %ee; enantioselective reaction; Inert atmosphere;
DOI:10.1021/jo102511x

Reference yield: 44.0%

: 53063-63-1
5-hydroxy-3-oxo-5-phenyl-valeric acid methyl ester

: 1838-94-4
isoprene epoxide

: 1287701-97-6
C₁₇H₂₂O₅

: methyl (4S)-2-hydroxy-2-(2-hydroxy-2-phenylethyl)-4-methyl-4-vinyltetrahydrofuran-3-carboxylate

: 1289155-41-4
methyl (4R)-2-hydroxy-2-(2-hydroxy-2-phenylethyl)-4-methyl-4-vinyltetrahydrofuran-3-carboxylate

Guidance literature:: With tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; (1R,2R)-1,2-bis[(2-diphenylphosphanyl)benzoylamino]cyclohexane; In dichloromethane; at 20 ℃; optical yield given as %ee; enantioselective reaction; Inert atmosphere;
DOI:10.1021/jo102511x

Reference yield:

: 100-52-7
benzaldehyde

: 1289155-41-4
methyl (4R)-2-hydroxy-2-(2-hydroxy-2-phenylethyl)-4-methyl-4-vinyltetrahydrofuran-3-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

1.1: sodium hydride / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere

1.2: 0.5 h / -15 - -10 °C

2.1: tris(dibenzylideneacetone)dipalladium(0) chloroform complex; (1R,2R)-(+)-1,2-diaminocyclohexane-N,N’-bis(2-diphenylphosphino-1-naphthoyl) / dichloromethane / 20 °C / Inert atmosphere

2.2: 0.5 h / 20 °C / Inert atmosphere

With tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; sodium hydride; (1R,2R)-(+)-1,2-diaminocyclohexane-N,N’-bis(2-diphenylphosphino-1-naphthoyl); In tetrahydrofuran; dichloromethane;
DOI:10.1021/jo102511x