(1R,4S)-4-(5-(benzyloxy)-1-ethoxy-2-(ethoxycarbonyl)-1-oxopentan-2-yl)cyclobut-2-enecarboxylic acid

Base Information

Chemical Name:(1R,4S)-4-(5-(benzyloxy)-1-ethoxy-2-(ethoxycarbonyl)-1-oxopentan-2-yl)cyclobut-2-enecarboxylic acid
CAS No.:1399219-88-5
Molecular Formula:C₂₂H₂₈O₇
Molecular Weight:404.46
Hs Code.:

Synonyms:(1R,4S)-4-(5-(benzyloxy)-1-ethoxy-2-(ethoxycarbonyl)-1-oxopentan-2-yl)cyclobut-2-enecarboxylic acid

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Chemical Property of (1R,4S)-4-(5-(benzyloxy)-1-ethoxy-2-(ethoxycarbonyl)-1-oxopentan-2-yl)cyclobut-2-enecarboxylic acid

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Technology Process of (1R,4S)-4-(5-(benzyloxy)-1-ethoxy-2-(ethoxycarbonyl)-1-oxopentan-2-yl)cyclobut-2-enecarboxylic acid

There total 3 articles about (1R,4S)-4-(5-(benzyloxy)-1-ethoxy-2-(ethoxycarbonyl)-1-oxopentan-2-yl)cyclobut-2-enecarboxylic acid 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: 76.0%

: 82258-55-7
Ethyl 5-benzyloxy-2-(ethoxycarbonyl)pentanoate

: rac-trans-4-chlorocyclobut-2-enecarboxylic acid

: 1399219-88-5
(1R,4S)-4-(5-(benzyloxy)-1-ethoxy-2-(ethoxycarbonyl)-1-oxopentan-2-yl)cyclobut-2-enecarboxylic acid

Guidance literature:: Ethyl 5-benzyloxy-2-(ethoxycarbonyl)pentanoate; With sodium hydride; In acetonitrile; mineral oil; at 20 ℃; for 0.25h; Inert atmosphere;

With bis(η3-allyl-μ-chloropalladium(II)); (3,5-Dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-((R)-1-phenyl-ethyl)-amine; In acetonitrile; mineral oil; for 0.25h; Inert atmosphere;

rac-trans-4-chlorocyclobut-2-enecarboxylic acid; In acetonitrile; mineral oil; at 0 ℃; for 14h; optical yield given as %ee; enantioselective reaction; Inert atmosphere;
DOI:10.1002/anie.201202853

Reference yield:

: 22980-23-0
5-oxabicyclo<2.2.0>hex-2-en-6-one

: 1399219-88-5
(1R,4S)-4-(5-(benzyloxy)-1-ethoxy-2-(ethoxycarbonyl)-1-oxopentan-2-yl)cyclobut-2-enecarboxylic acid

Guidance literature:: Multi-step reaction with 2 steps

1.1: hydrogenchloride / diethyl ether / 20 h / -10 °C / Molecular sieve; Inert atmosphere

2.1: sodium hydride / acetonitrile; mineral oil / 0.25 h / 20 °C / Inert atmosphere

2.2: 0.25 h / Inert atmosphere

2.3: 14 h / 0 °C / Inert atmosphere

With hydrogenchloride; sodium hydride; In diethyl ether; acetonitrile; mineral oil;
DOI:10.1002/anie.201202853

Reference yield:

: 504-31-4
pyran-2-one

: 1399219-88-5
(1R,4S)-4-(5-(benzyloxy)-1-ethoxy-2-(ethoxycarbonyl)-1-oxopentan-2-yl)cyclobut-2-enecarboxylic acid

Guidance literature:: Multi-step reaction with 3 steps

1.1: diethyl ether / -10 °C / UV-irradiation; Inert atmosphere

2.1: hydrogenchloride / diethyl ether / 20 h / -10 °C / Molecular sieve; Inert atmosphere

3.1: sodium hydride / acetonitrile; mineral oil / 0.25 h / 20 °C / Inert atmosphere

3.2: 0.25 h / Inert atmosphere

3.3: 14 h / 0 °C / Inert atmosphere

With hydrogenchloride; sodium hydride; In diethyl ether; acetonitrile; mineral oil;
DOI:10.1002/anie.201202853