74985-54-9

Upstream product

• 74965-59-6 3-Oxo-hept-6-enoic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester 
• 2216-51-5 (-)-menthol 
• 59557-05-0 (L)-menthyl 3-oxobutyrate 
• 111594-56-0 2-oxobicyclo<3.1.0>hexane-1-carboxylic acid 
• 61996-11-0 2-oxo-bicyclo[3.1.0]hexane-1-carboxylic acid methyl ester 

Downstream Products

• 135447-02-8 (1R,3S,5S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-methylene-bicyclo[3.1.0]hexane-1-carboxylic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester 
• 32222-06-3 calcitriol 
• 101046-92-8 (1S)-1-methoxymethoxyvitamin D₃ 
• 101046-90-6 (-)-menthyl (1R,3S,5S)-3-methoxymethoxy-2-methylenebicyclo<3.1.0>hexane-1-carboxylate 
• 111594-57-1 (1R,5S)-2-Methylene-3-oxo-bicyclo[3.1.0]hexane-1-carboxylic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester 
• 101046-89-3 (1R,3S,5S)-3-Hydroxy-2-methylene-bicyclo[3.1.0]hexane-1-carboxylic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester 
• 41294-56-8 1α-hydroxyvitamin D3 
• 93489-96-4 (-)-menthyl (1R,5R)-2-methylenebicyclo<3.1.0>hexane-1-carboxylate 
• 74965-62-1 (1R,2S)-2-Methyl-5-oxo-cyclopentanecarboxylic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester 
• 93489-96-4 (1R,5R)-2-Methylene-bicyclo[3.1.0]hexane-1-carboxylic acid (1S,2R)-2-isopropyl-5-methyl-cyclohexyl ester 

Relevant academic research and scientific papers

A Stereoselective Synthesis of 1α-Hydroxyvitamin D3

A stereoslelective synthesis of 1α-hydroxyvitamin D3 (16) was achieved through the solvolysis of the 3,5-cyclovitamin D3 (14) which was prepared form (-)-(1R,3S,5S)-3-methoxymethoxy-2-methylenebicyclohexanecarbaldehyde (13) and 8-bromomethylenedes-AB-cholestane (1).

Preparation of Cyclohexanones and Cyclopentanones of High Optical Purity

Cyclization of 3, prepared from 1-menthol, led to a 1:1 mixture of 4 and 5.These diastereomeric ketones, readily separated by chromatography, are versatile intermediates for the preparation of alkylated cyclohexanones.The absolute configuration of 5 was assigned by conversion to the known hydroxy ketal 9.This approach works equally well for the cyclopentane series.Thus, alkylated cyclohexanones and cyclopentanones of known absolute configuration will for the first time be routinely available.