90898-48-9

Upstream product

• 137610-12-9 (5S)-5-hydroxymethyl-3-methyl-4,5-dihydroisoxazole 
• 75-93-4 methyl bisulfate 
• 138809-92-4 (S)-6-((S)-1-Benzyloxy-pentyl)-4-hydroxy-5,6-dihydro-pyran-2-one 
• 136850-73-2 (1S^*,6S^*)-6-(1-benzyloxypentyl)-3,4,5,6-tetrahydropyran-2,4-dione 
• 77-78-1 dimethyl sulfate 
• 141554-39-4 (6S,1'S)-6-(1'-benzyloxypentyl)-5,6-dihydropyran-2,4(3H)-dione 
• 66832-04-0 methyl 6-benzyloxy-5-hydroxy-3-oxodecanoate 
• 141554-36-1 2-(benzyloxy)hexan-1-ol 
• 110320-68-8 methyl 2-benzyloxyhexanoate 
• 68756-64-9 2-hydroxyhexanoic acid methyl ester 
• 636-36-2 rac-2-hydroxyhexanoic acid 
• 70326-39-5 α-benzyloxyhexanal 
• 90857-62-8 ((E)-1,3-Dimethoxy-buta-1,3-dienyloxy)-trimethyl-silane 
• 54620-77-8 methyl (5R, 6RS)-6-benzyloxy-5-hydroxy-2-decyonate 

Downstream Products

• 52305-12-1 (6R,1'R)-(+)-5,6-dihydro-6-(1'-hydroxypentyl)-4-methoxy-pyran-2-one 
• 34565-32-7 (6R, 1'S)-(+)-epipestalotin 
• 34565-32-7 (+/-) epi-pestalotin 
• 34565-32-7 (S)-6-((S)-1-hydroxypentyl)-4-methoxy-5,6-dihydro-2H-pyran-2-one 

Relevant academic research and scientific papers

Divergent asymmetric total synthesis of all four pestalotin diastereomers from (R)-glycidol

All four chiral pestalotin diastereomers were synthesized in a straightforward and divergent manner from common (R)-glycidol. Catalytic asymmetric Mukaiyama aldol reactions of readily-available bis(TMSO)diene (Chan’s diene) with (S)-2-benzyloxyhexanal der

High Diastereoselection in the Aldol Reaction of the Bistrimethylsilyl Enol Ether of Methyl Acetoacetate with 2-Benzyloxyhexanal: Synthesis of (-)-Pestalotin

Aldol condensation of the bistrimethylsilyl enol ether of methyl acetoacetate, compound 2, with 2-benzyloxyhexanal 3c affords highly selectively (99:1) the syn-aldol adduct 4c in the presence of titanium tetrachloride.The stereocontrolled synthesis of (-)-pestalotin 7 has been achieved.

Stereoselective Synthesis of 1,2-Diols by the Cycloadditive Strategy: Total Synthesis of (+/-)-exo-Brevicomin and (+/-)- and (-)-Pestalotin

Highly selective reductions of 5-acyl-2-isoxazolines and conversion of the resulting syn-5-hydroxyalkyl-2-isoxazolines into syn-diols are key steps in concise syntheses of (+/-)-exo-brevicomin, and (+/-)-pestalotin.With an asymmetric nitrile oxide as starting material, cycloaddition with the acrylate derivative of Oppolzer's camphor sultam leads to a synthesis of (-)-pestalotin.

A stereoselective synthesis of (±)-pestalotin

(±)-Pestalotin was synthesized by employing a stereoselective reduction of a 5-alkyltetronate derivative and a two-carbon elongation reaction of the aldehyde with ethyl diazoacetate in the presence of stannous chloride as key steps.

Highly Diastereoselective Titanium Tetrachloride-mediated Aldol Condensation of the Bistrimethylsilyl Enol Ether of Acetoacetic Ester with 2-Benzyloxyhexanal. A Synthesis of (-)-Pestalotin

Titanium tetrachloride-mediated aldol condensation of the bistrimethylsilyl enol ether of methyl acetoacetate (1) with 2-benzyloxyhexanal (3) gives highly selectively (99:1) the syn aldol adduct (5); the stereocontrolled synthesis of (-)-pestalotin (9) ha