202122-47-2

Upstream product

• 202122-36-9 (S)-4-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-pentanal 
• 156633-81-7 (2R,3S)-3,7-dimethyl-6-octene-1,2-diol 
• 76985-26-7 (2S,3R)-3,7-dimethyl-2,3-epoxy-6-octen-1-ol 
• 98-59-9 p-toluenesulfonyl chloride 
• 202122-37-0 (S)-4-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-pentan-1-ol 
• 202122-35-8 (R)-4-((S)-1,5-Dimethyl-hex-4-enyl)-2,2-dimethyl-[1,3]dioxolane 

Downstream Products

• 479484-94-1 (2R,3S,10S,5Z)-2-benzyloxy-10-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]undec-5-en-3-ol 
• 479484-93-0 (2R,3S,10S)-2-benzyloxy-10-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]undec-5-yn-3-ol 

Relevant academic research and scientific papers

Chiral synthesis of the C3-13 segment of epothilone A

Synthesis of the title compound using inexpensive geraniol as starting material in 13 steps and in 10.6% overal yield is described. Epothilone A and B are a new class of macrolides, which possess striking biological activities.1 Most importantl

Total synthesis of epothilone A through stereospecific epoxidation of the p-methoxybenzyl ether of epothilone C

The total synthesis of epothilone A is described by the coupling four segments 4 - 7a. Three of the segments, 4, 5 and 7a, have only one chiral center; all other chiral centers were introduced by simple asymmetric catalytic reactions. The key steps are the ring opening of epoxide 5 with acetylide 8 for the construction of the C12-C13 cis double bond and a practical hydrolytic kinetic resolution (HKR) developed by Jacobsen group for the introduction the chiral center at C3. Especially, the stereospecific epoxidation of 3-O-PMB epothilone C 3b through long-range effect of 3-O-PMB protecting group gave high yields of the C12 - C13 α-epoxide for the synthesis of target molecule.