(1R,2R,3S,4S)-<3--2-bornyl>-(1S,5S)-5-vinyl-2-oxo-cyclopentanecarboxylate

Base Information

Chemical Name:(1R,2R,3S,4S)-<3--2-bornyl>-(1S,5S)-5-vinyl-2-oxo-cyclopentanecarboxylate
CAS No.:676345-39-4
Molecular Formula:C₃₂H₃₉NO₅S
Molecular Weight:549.731
Hs Code.:

(1R,2R,3S,4S)-<3-<N-benzenesulfonyl-N-(3,5-dimethylphenyl)-amino>-2-bornyl>-(1S,5S)-5-vinyl-2-oxo-cyclopentanecarboxylate

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (1R,2R,3S,4S)-<3--2-bornyl>-(1S,5S)-5-vinyl-2-oxo-cyclopentanecarboxylate

Chemical Property:

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Technology Process of (1R,2R,3S,4S)-<3--2-bornyl>-(1S,5S)-5-vinyl-2-oxo-cyclopentanecarboxylate

There total 8 articles about (1R,2R,3S,4S)-<3--2-bornyl>-(1S,5S)-5-vinyl-2-oxo-cyclopentanecarboxylate 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:

: 87360-02-9
N-(3,5-Dimethyl-phenyl)-N-((1S,2S,3R,4R)-3-hydroxy-4,7,7-trimethyl-bicyclo[2.2.1]hept-2-yl)-benzenesulfonamide

: 676345-39-4
(1R,2R,3S,4S)-<3--2-bornyl>-(1S,5S)-5-vinyl-2-oxo-cyclopentanecarboxylate

Guidance literature:: Multi-step reaction with 4 steps

1.1: C₆H₅N(CH₃)2

2.1: NaH

3.1: copper(I) cyanide; BF₃*Et₂O / diethyl ether / -80 °C

3.2: diethyl ether / 18 h / -80 - 20 °C

With boron trifluoride diethyl etherate; copper(l) cyanide; sodium hydride; N,N-dimethyl-aniline; In diethyl ether; 2.1: Michael-Arbuzov reaction / 3.2: Wittig-Horner reaction;
DOI:10.1055/s-2003-45008

Reference yield:

: 917-57-7
vinyllithium

: (E)-Hex-2-enedioic acid 1-{(1R,2R,3S,4S)-3-[benzenesulfonyl-(3,5-dimethyl-phenyl)-amino]-1,7,7-trimethyl-bicyclo[2.2.1]hept-2-yl} ester 6-methyl ester

: 676345-39-4
(1R,2R,3S,4S)-<3--2-bornyl>-(1S,5S)-5-vinyl-2-oxo-cyclopentanecarboxylate

: (1R,5S)-2-Oxo-5-vinyl-cyclopentanecarboxylic acid (1R,2R,3S,4S)-3-[benzenesulfonyl-(3,5-dimethyl-phenyl)-amino]-1,7,7-trimethyl-bicyclo[2.2.1]hept-2-yl ester

Guidance literature:: vinyllithium; With boron trifluoride diethyl etherate; copper(l) cyanide; In diethyl ether; at -80 ℃;

(E)-Hex-2-enedioic acid 1-{(1R,2R,3S,4S)-3-[benzenesulfonyl-(3,5-dimethyl-phenyl)-amino]-1,7,7-trimethyl-bicyclo[2.2.1]hept-2-yl} ester 6-methyl ester; In diethyl ether; at -80 - 20 ℃; for 18h; Title compound not separated from byproducts;
DOI:10.1055/s-2003-45008

Reference yield:

: 611-10-9
2-ethoxycarbonyl-1-cyclopentanone

: 676345-39-4
(1R,2R,3S,4S)-<3--2-bornyl>-(1S,5S)-5-vinyl-2-oxo-cyclopentanecarboxylate

Guidance literature:: Multi-step reaction with 4 steps

1: 98 percent / DMAP / toluene / 48 h / Heating

2: 41 percent / pyridine / CH₂Cl₂ / 2 h / 20 °C

3: 90 percent / mCPBA / CH₂Cl₂ / 2 h / 20 °C

4: 1.) lithium 2-thienylcyanocuprate / 1.) THF, -78 deg C, 1 h, 2.) THF, -78 deg C, 2 h

With pyridine; dmap; thien-2-yl(cyano)copper lithium; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; toluene;
DOI:10.1016/0040-4020(95)00951-5