265656-41-5

Upstream product

• 917-54-4 methyllithium 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 265656-39-1 2-((2R,3S,6R)-3-Benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-ethanol 
• 265656-38-0 (1R,5R,6S)-6-benzyloxy-1-methyl-2,9-dioxabicyclo[3.3.1]nonane 
• 265656-33-5 (R)-4-((S)-1-Benzyloxy-but-3-enyl)-2-phenyl-[1,3]dioxane 
• 265656-34-6 (S)-4-Benzyloxy-4-((R)-2-phenyl-[1,3]dioxan-4-yl)-butan-1-ol 
• 265656-37-9 (S)-5-Benzyloxy-5-((R)-2-phenyl-[1,3]dioxan-4-yl)-pentan-2-one 
• 265656-36-8 (1R,5R,6S)-6-benzyloxy-2,9-dioxabicyclo[3.3.1]nonane 
• 544704-58-7 (2R,3S,6R)-6-methyl-3-(phenylmethoxy)-tetrahydro-2H-pyran-2-acetaldehyde 
• 544704-44-1 2,6-anhydro-1,3,4-trideoxy-4-O-(phenylmethyl)-D-arabino-heptitol 6-methylbenzenesulfonate 
• 544704-46-3 6-methyl-3-(phenylmethoxy)-tetrahydro-2H-pyran-2-acetonitrile 
• 544704-62-3 2-((3S,6R)-3-Benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-ethanol 
• 544704-40-7 2,6-anhydro-1,3,4-trideoxy-4,6-O-(phenylmethylene)-D-arabino-heptitol 

Relevant academic research and scientific papers

Synthesis of (+)-decarestrictine L

A synthesis of (+)-decarestrictine L 1, a cholesterol biosynthesis inhibitory metabolite isolated from Penicillium simplicissimum, is described. Beginning from tri-O-acetyl-D-glucal, alkylation with trimethylaluminum introduced the axial methyl group at C-2 in a stereoselective fashion. Chain extension at the C-6 carbon was accomplished by generation of the primary tosylate, followed by displacement with cyanide anion. The synthesis of (+)-1 was completed in 13 steps and 6.3% overall yield.

Enantioselective synthesis of (+)-decarestrictine L from (2E,5E)- dibenzyloxy-2,5-heptadien-4-ol

(+)-Decarestrictine L has been synthesized in enantiomerically pure form from (3R,4S)-1-benzyloxy-6-heptene-3,4-diol, prepared from (2E,5E)-1,7- dibenzyloxy-2,5-heptadien-4-ol, employing either Me2AlCl promoted methylative cleavage of (1R,5R,6S