88908-94-5

Upstream product

• 98758-87-3 (+/-)-α-cyclohexylidenemethyl-3-methoxymethoxy-2-methylenebicyclo<3.1.0>hexane-1-methanol 
• 88908-90-1 (+/-)-methyl 3β-methoxymethoxy-2-methylenebicyclo<3.1.0>hexane-1-carboxylate 
• 61996-11-0 2-oxo-bicyclo[3.1.0]hexane-1-carboxylic acid methyl ester 
• 88908-90-1 (3S,5S)-3-Methoxymethoxy-2-methylene-bicyclo[3.1.0]hexane-1-carboxylic acid methyl ester 
• 88908-89-8 (3S,5S)-3-Hydroxy-2-methylene-bicyclo[3.1.0]hexane-1-carboxylic acid methyl ester 
• 88908-92-3 (3S,5S)-3-Methoxymethoxy-2-methylene-bicyclo[3.1.0]hexane-1-carbaldehyde 
• 88908-91-2 ((3S,5S)-3-Methoxymethoxy-2-methylene-bicyclo[3.1.0]hex-1-yl)-methanol 
• 88908-87-6 2-Methylene-bicyclo[3.1.0]hexane-1-carboxylic acid methyl ester 
• 88908-91-2 (+/-)-3β-methoxymethoxy-2-methylenebicyclo<3.1.0>hexane-1-methanol 
• 88908-89-8 (+/-)-methyl 3β-hydroxy-2-methylenebicyclo<3.1.0>hexane-1-carboxylate 
• 88908-87-6 (+/-)-methyl 2-methylenebicyclo<3.1.0>hexane-1-carboxylate 
• 88908-93-4 (+/-)-2-hydroxy-2-<(3β-methoxymethoxy-2-methylenebicyclo<3.1.0>hexane)-1>ethylidenecyclohexane 
• 88908-92-3 (+/-)-formyl-3β-methoxymethoxy-2-methylenebicyclo<3.1.0>hexane 

Downstream Products

• 88908-95-6 (+/-)-(Z)-2-(3β,5α-dihydroxy-2-methylene-cyclohexylidene)ethylidenecyclohexane 

Relevant academic research and scientific papers

A General Method for the Synthesis of 3,5-Cyclovitamin D3 and Derivatives. A Stereoselective Synthesis of Vitamin D3

A stereoselective synthesis of vitamin D3 (1) was achieved via 3,5-cyclovitamin D3 (33) which was synthesized from the chiral aldehyde (3) and the vinyl bromide (27) derived from Grundmann's ketone (25). (+/-)-(Z)-5-(2-Cyclohexylidene-ethylidene)-4-methylenecyclohexane-r-1, t-3-diol (24) as a model compound of 1α-hydroxyvitamin D3 was also stereoselectively synthesized via the solvolysis of (+/-)-α-cyclohexylidenemethyl-3β-methoxymethoxy-2-methylenebicyclohexane-1-methanol (21) which was prepared from the aldehyde (12) and the organostannane (16).

SYNTHETIC STUDIES TOWARD TO 1α-HYDROXYVITAMIN D3 --- STEREOSELECTIVE SYNTHESIS OF (+/-)-(Z)-2-(3β,5α-DIHYDROXY-2-METHYLENECYCLOHEXYLIDENE)ETHYLIDENECYCLOHEXANE

As a model experiment for a synthesis of 1α-hydroxyvitamin D3, the title compound (19) was stereoselectively synthesized via the solvolysis of (+/-)-2-hydroxy-2-hexane)-1>ethylidenecyclohexane (15).