[3R-(3a,3ab,4b,5a,6b,6ab,7R*)]-6-bromohexahydro-2-oxo-4-(trimethylsilyl)-3,5-methano-2H-cyclopenta[b]furan-7-carboxylic acid (1R)-menthyl ester

Base Information

Chemical Name:[3R-(3a,3ab,4b,5a,6b,6ab,7R*)]-6-bromohexahydro-2-oxo-4-(trimethylsilyl)-3,5-methano-2H-cyclopenta[b]furan-7-carboxylic acid (1R)-menthyl ester
CAS No.:153750-14-2
Molecular Formula:C₂₂H₃₅BrO₄Si
Molecular Weight:471.507
Hs Code.:

Synonyms:[3R-(3a,3ab,4b,5a,6b,6ab,7R*)]-6-bromohexahydro-2-oxo-4-(trimethylsilyl)-3,5-methano-2H-cyclopenta[b]furan-7-carboxylic acid (1R)-menthyl ester

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Chemical Property of [3R-(3a,3ab,4b,5a,6b,6ab,7R*)]-6-bromohexahydro-2-oxo-4-(trimethylsilyl)-3,5-methano-2H-cyclopenta[b]furan-7-carboxylic acid (1R)-menthyl ester

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Technology Process of [3R-(3a,3ab,4b,5a,6b,6ab,7R*)]-6-bromohexahydro-2-oxo-4-(trimethylsilyl)-3,5-methano-2H-cyclopenta[b]furan-7-carboxylic acid (1R)-menthyl ester

There total 3 articles about [3R-(3a,3ab,4b,5a,6b,6ab,7R*)]-6-bromohexahydro-2-oxo-4-(trimethylsilyl)-3,5-methano-2H-cyclopenta[b]furan-7-carboxylic acid (1R)-menthyl ester 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: 99.0%

: 153750-13-1
[1R-(2-endo,3-exo,7-anti)]-7-trimethylsilylbicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid di[(1R)-menthyl] ester

: 153750-14-2
[3R-(3a,3ab,4b,5a,6b,6ab,7R*)]-6-bromohexahydro-2-oxo-4-(trimethylsilyl)-3,5-methano-2H-cyclopenta[b]furan-7-carboxylic acid (1R)-menthyl ester

Guidance literature:: With bromine; In dichloromethane; at 0 - 20 ℃; Inert atmosphere;
DOI:10.1002/anie.200803284

Reference yield:

: 3559-74-8
trimethylsilylcyclopentadiene

: 153750-14-2
[3R-(3a,3ab,4b,5a,6b,6ab,7R*)]-6-bromohexahydro-2-oxo-4-(trimethylsilyl)-3,5-methano-2H-cyclopenta[b]furan-7-carboxylic acid (1R)-menthyl ester

Guidance literature:: Multi-step reaction with 2 steps

1.1: diethylaluminum chloride / toluene; hexane / 1 h / -78 °C

1.2: 90 percent / toluene; hexane / 1 h / -78 °C

2.1: 97.4 percent / bromine / CH₂Cl₂ / 72 h / 20 °C

With bromine; diethylaluminium chloride; In hexane; dichloromethane; toluene;
DOI:10.1248/cpb.52.1367

Reference yield:

: 34675-24-6
di-L-menthyl fumarate

: 153750-14-2
[3R-(3a,3ab,4b,5a,6b,6ab,7R*)]-6-bromohexahydro-2-oxo-4-(trimethylsilyl)-3,5-methano-2H-cyclopenta[b]furan-7-carboxylic acid (1R)-menthyl ester

Guidance literature:: Multi-step reaction with 2 steps

1.1: diethylaluminum chloride / toluene; hexane / 1 h / -78 °C

1.2: 90 percent / toluene; hexane / 1 h / -78 °C

2.1: 97.4 percent / bromine / CH₂Cl₂ / 72 h / 20 °C

With bromine; diethylaluminium chloride; In hexane; dichloromethane; toluene;
DOI:10.1248/cpb.52.1367