147618-57-3

Upstream product

• 86462-75-1 (Z)-5-<(1,1-dimethylethyl)dimethylsilyloxy>pent-2-en-1-ol 
• 111466-32-1 (2S,3R)-4-t-butyldimethylsilyloxy-2,3-epoxy-pentan-1-ol 
• 98-59-9 p-toluenesulfonyl chloride 

Downstream Products

• 137369-78-9 (2S,3S)-4-t-butyldimethylsilyloxy-3-chloropentane-1,2-diol 1-tosylate 
• 174874-04-5 (5S,6R)-(2E)-8-t-butyldimethylsilyloxy-5,6-epoxy-2-octen-1-ol 1-benzoate 
• 174874-05-6 (5R,6R)-(2E)-1-benzoyloxy-5-bromo-2-octene-6,8-diol 8-pivaloate 
• 174874-06-7 (5R,6R)-(2E)-1-benzoyloxy-5-bromo-6-t-butyldimethylsilyloxy-2-octene-8-ol 8-pivaloate 
• 174874-09-0 (2R,3R,5R,6R)-5-bromo-6-t-butyldimethylsilyloxy-2,3-epoxy-1-p-toluenesulfonyloxyoctan-8-ol 8-pivaloate 

Relevant academic research and scientific papers

Total synthesis of (-)-dactylynes

The first total synthesis of (-)-dactylyne (1) and (-)-isodactylyne (2), which have been isolated from sea hare, is described in detail. Critical steps in the synthesis include a stereoselective construction as well as an intramolecular ring closure of 32, and the effective double elongation reactions (59 → 63 and 64, 67 → 68, and 70 → 71).

Highly Regioselective Ring Opening of 2,3-Epoxy Alcohol Methanesulfonates

Reaction of 2,3-epoxy-1-ol methanesulfonates with diethylaluminum chloride or with the mixture of diethylaluminum chloride and diethylamine hydrobromide in dichloromethane gave rise to regioselectively the corresponding 3-chloro- and 3-bromo-1,2-diol 1-methanesulfonates, respectively, in excellent yields.