(3S,4R)-benzyl 3-(3-methoxy-3-oxopropyl)-4-(3-methoxyphenyl)-2-oxotetrahydrofuran-3-carboxylate

Base Information

Chemical Name:(3S,4R)-benzyl 3-(3-methoxy-3-oxopropyl)-4-(3-methoxyphenyl)-2-oxotetrahydrofuran-3-carboxylate
CAS No.:1373247-33-6
Molecular Formula:C₂₃H₂₄O₇
Molecular Weight:412.439
Hs Code.:

Synonyms:(3S,4R)-benzyl 3-(3-methoxy-3-oxopropyl)-4-(3-methoxyphenyl)-2-oxotetrahydrofuran-3-carboxylate

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Chemical Property of (3S,4R)-benzyl 3-(3-methoxy-3-oxopropyl)-4-(3-methoxyphenyl)-2-oxotetrahydrofuran-3-carboxylate

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Technology Process of (3S,4R)-benzyl 3-(3-methoxy-3-oxopropyl)-4-(3-methoxyphenyl)-2-oxotetrahydrofuran-3-carboxylate

There total 6 articles about (3S,4R)-benzyl 3-(3-methoxy-3-oxopropyl)-4-(3-methoxyphenyl)-2-oxotetrahydrofuran-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: 90.0%

: 1373247-32-5
(3R,4S)-benzyl 4-(3-methoxyphenyl)-2-oxotetrahydrofuran-3-carboxylate

: 292638-85-8,9003-21-8,96-33-3
acrylic acid methyl ester

: 1373247-33-6
(3S,4R)-benzyl 3-(3-methoxy-3-oxopropyl)-4-(3-methoxyphenyl)-2-oxotetrahydrofuran-3-carboxylate

Guidance literature:: With potassium carbonate; In N,N-dimethyl-formamide; at 70 ℃; for 0.166667h; Inert atmosphere;
DOI:10.1002/anie.201109221

Reference yield:

: 501-53-1,94274-21-2
benzyl chloroformate

: 292638-85-8,9003-21-8,96-33-3
acrylic acid methyl ester

: (S)-4-(3-methoxyphenyl)dihydrofuran-2(3H)-one

: 1373247-33-6
(3S,4R)-benzyl 3-(3-methoxy-3-oxopropyl)-4-(3-methoxyphenyl)-2-oxotetrahydrofuran-3-carboxylate

Guidance literature:: benzyl chloroformate; (S)-4-(3-methoxyphenyl)dihydrofuran-2(3H)-one; With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃;

acrylic acid methyl ester; With potassium carbonate; In N,N-dimethyl-formamide; at 70 ℃; diastereoselective reaction;
DOI:10.1248/cpb.c16-00256

Reference yield:

: 7706-85-6
4-(3-methoxyphenyl)furan-2(5H)-one

: 1373247-33-6
(3S,4R)-benzyl 3-(3-methoxy-3-oxopropyl)-4-(3-methoxyphenyl)-2-oxotetrahydrofuran-3-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

1.1: (S)-(+)-4,4'-bis[di(3,5-di-tert-butyl-4-methoxyphenyl)phosphino]-3,3'-bi(1,2-methylenedioxybenzene); copper(l) chloride; sodium t-butanolate; tert-butyl alcohol / tetrahydrofuran / 15 h / 20 °C / Inert atmosphere

2.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere

2.2: 0.17 h / -78 °C / Inert atmosphere

3.1: potassium carbonate / N,N-dimethyl-formamide / 0.17 h / 70 °C / Inert atmosphere

With (S)-(+)-4,4'-bis[di(3,5-di-tert-butyl-4-methoxyphenyl)phosphino]-3,3'-bi(1,2-methylenedioxybenzene); potassium carbonate; copper(l) chloride; lithium hexamethyldisilazane; sodium t-butanolate; tert-butyl alcohol; In tetrahydrofuran; N,N-dimethyl-formamide; 3.1: Michael addition;
DOI:10.1002/anie.201109221