(5R)-ethyl 5-((1R,2R)-1-(benzyloxy)-2-(methoxymethoxy)but-3-enyl)-2-oxotetrahydrofuran-3-carboxylate

Base Information

Chemical Name:(5R)-ethyl 5-((1R,2R)-1-(benzyloxy)-2-(methoxymethoxy)but-3-enyl)-2-oxotetrahydrofuran-3-carboxylate
CAS No.:1378374-53-8
Molecular Formula:C₂₀H₂₆O₇
Molecular Weight:378.422
Hs Code.:

Synonyms:(5R)-ethyl 5-((1R,2R)-1-(benzyloxy)-2-(methoxymethoxy)but-3-enyl)-2-oxotetrahydrofuran-3-carboxylate

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Chemical Property of (5R)-ethyl 5-((1R,2R)-1-(benzyloxy)-2-(methoxymethoxy)but-3-enyl)-2-oxotetrahydrofuran-3-carboxylate

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Technology Process of (5R)-ethyl 5-((1R,2R)-1-(benzyloxy)-2-(methoxymethoxy)but-3-enyl)-2-oxotetrahydrofuran-3-carboxylate

There total 2 articles about (5R)-ethyl 5-((1R,2R)-1-(benzyloxy)-2-(methoxymethoxy)but-3-enyl)-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:

: 112531-79-0
(3R,4R)-4-(methoxymethoxy)hexa-1,5-dien-3-ol

: 1378374-53-8
(5R)-ethyl 5-((1R,2R)-1-(benzyloxy)-2-(methoxymethoxy)but-3-enyl)-2-oxotetrahydrofuran-3-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

1.1: titanium(IV) isopropylate; L-(+)-diisopropyl tartrate / dichloromethane / 0.25 h / -20 °C / Molecular sieve; Inert atmosphere

1.2: 72 h / -10 °C / Molecular sieve; Inert atmosphere

2.1: sodium hydride / mineral oil / 16 h / 0 - 20 °C

3.1: ethanol; sodium / 0.17 h

3.2: 16 h / Reflux

With titanium(IV) isopropylate; ethanol; L-(+)-diisopropyl tartrate; sodium; sodium hydride; In dichloromethane; mineral oil; 1.1: Sharpless epoxidation / 1.2: Sharpless epoxidation;
DOI:10.1002/jccs.201100587

Reference yield:

: 207679-21-8
(1S,2R)-2-(methoxymethoxy)-1-((R)-oxiran-2-yl)but-3-en-1-ol

: 1378374-53-8
(5R)-ethyl 5-((1R,2R)-1-(benzyloxy)-2-(methoxymethoxy)but-3-enyl)-2-oxotetrahydrofuran-3-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

1.1: sodium hydride / mineral oil / 16 h / 0 - 20 °C

2.1: ethanol; sodium / 0.17 h

2.2: 16 h / Reflux

With ethanol; sodium; sodium hydride; In mineral oil;
DOI:10.1002/jccs.201100587

Reference yield: 87.0%

: 1378374-53-8
(5R)-ethyl 5-((1R,2R)-1-(benzyloxy)-2-(methoxymethoxy)but-3-enyl)-2-oxotetrahydrofuran-3-carboxylate

: 1378374-46-9
(R)-5-((1R,2R)-1-(benzyloxy)-2-(methoxymethoxy)but-3-enyl)dihydrofuran-2(3H)-one

Guidance literature:: (5R)-ethyl 5-((1R,2R)-1-(benzyloxy)-2-(methoxymethoxy)but-3-enyl)-2-oxotetrahydrofuran-3-carboxylate; With lithium hydroxide; In 1,2-dimethoxyethane; water; at 50 ℃; for 6h;

With hydrogenchloride; In water; at 20 ℃; pH=3;
DOI:10.1002/jccs.201100587