210764-97-9

Upstream product

• 824-94-2 p-methoxybenzyl chloride 
• 222545-14-4 methyl 6-deoxy-6-iodo-2,3-di-O-(4-methoxy)benzyl-α-D-glucopyranoside 
• 222545-17-7 Dithiocarbonic acid O-[(1R,2S,5S,6R)-5,6-bis-(4-methoxy-benzyloxy)-2-(tetrahydro-pyran-2-yloxy)-cyclohex-3-enyl] ester S-methyl ester 
• 210764-95-7 (3S,4R,5R,6S)-5-acetoxy-3,4-di-(4-methoxybenzyl)oxy-6-(tetrahydropyran-2-yl)oxycyclohex-1-ene 
• 222545-16-6 (1R,2S,5S,6S)-5,6-di-(4-methoxybenzyl)oxy-2-(tetrahydropyran-2-yl)oxy-cyclohex-3-en-1-ol 
• 210764-92-4 methyl 4-O-acetyl-2,3-di-O-(4-methoxy)benzyl-α-D-xylo-hex-5-enopyranoside 
• 222545-15-5 Acetic acid (1S,2R,3S)-4-hydroxy-2,3-bis-(4-methoxy-benzyloxy)-6-oxo-cyclohexyl ester 
• 210764-94-6 (1S,4S,5R,6R)-2-acetoxy-4,5-di-(4-methoxybenzyl)oxy-cyclohex-2-en-1-ol 
• 199918-03-1 methyl 2,3-bis-O-(4-methoxybenzyl)-4,6-O-phenylmethylene-α-D-glucopyranoside 
• 222545-13-3 methyl 2,3-di-O-(4-methoxyphenylmethyl)-α-D-glucopyranoside 
• 210764-96-8 (3S,4S,6R)-3,4-di-(4-methoxybenzyl)oxy-6-(tetrahydropyran-2-yl)oxy-cyclohex-1-ene 

Downstream Products

• 210764-98-0 ethyl 2-<(1S,5S,6S)-5,6-di-(4-methoxybenzyl)oxy-cyclohex-2-en-1-yl>propionate 
• 222545-23-5 (1S,2S,3S,4R)-3-<(1E)-1,5-dimethylhexa-1,4-dien-1-yl>-4-(tert-butyldimethylsilyl)oxy-1,2-di-(4-methoxybenzyl)oxy-cyclohexane 
• 222545-22-4 (1S,2S,3S,4R)-3-<(1E)-3-chloro-1-methylprop-1-en-1-yl>-4-(tert-butyldimethylsilyl)oxy-1,2-di-(4-methoxybenzyl)oxy-cyclohexane 
• 222545-25-7 (1R,2R,3S,4S)-2-<(2R,3S)-3-(3-methyl-2-buten-1-yl)-2-methyloxiran-2-yl>-3,4-di-(4-methoxybenzyl)oxy-cyclohexan-1-ol 
• 222545-24-6 (1R,2R,3S,4S)-2-<(1E)-1,5-dimethylhexa-1,4-dien-1-yl>-1,2-di-(4-methoxybenzyl)oxy-cyclohexan-1-ol 
• 222545-27-9 (2S,3S,4S)-2-<(1E)-1,5-dimethylhexa-1,4-dien-1-yl>-1,2-di-(4-methoxybenzyl)oxy-cyclohexan-1-one 
• 222545-30-4 (1R,2R,3S,4S)-2-<(1E)-1-methylprop-1-en-1-yl>-3,4-di-(4-methoxybenzyl)oxy-cyclohexan-1-ol 
• 210765-04-1 (2E)-3-<(1S,2S,3S,6R)-6-(tert-butyldimethylsilyl)oxy-2,3-di-(4-methoxybenzyl)oxy-cyclohex-1-yl>but-2-enal 
• 103470-60-6 FR65814 
• 210765-07-4 (2E)-3-<(3R,4S,5S,6S)-5,6-di-(4-methoxybenzyl)oxy-1-oxaspiro<2.5>oct-4-yl>-1-(tert-butyldimethylsilyl)oxybut-2-ene 
• 210765-06-3 (2S,3S,4S)-2-<(1E)-3-(tert-butyldimethylsilyl)oxy-1-methylprop-1-en-1-yl>-3,4-di-(4-methoxybenzyl)oxy-cyclohexan-1-one 
• 222545-21-3 (2E)-3-<(1S,2S,3S,6R)-6-(tert-butyldimethylsilyl)oxy-2,3-di-(4-methoxybenzyl)oxy-cyclohex-1-yl>but-2-en-1-ol 
• 210765-02-9 (3R)-3-<(1S,2S,3S,6R)-6-(tert-butyldimethylsilyl)oxy-2,3-di-(4-methoxybenzyl)oxy-cyclohex-1-yl>butan-1-ol 
• 222545-32-6 (1R,2R,3S,4S)-2-<(1E)-3-(tert-butyldimethylsilyl)oxy-1-methylprop-1-en-1-yl>-3,4-di-(4-methoxybenzyl)oxy-cyclohexan-1-ol 

Relevant academic research and scientific papers

Chiral and stereoselective total synthesis of novel immunosuppressant FR65814 from D-glucose

The chiral synthesis of the immunosuppressive sesquiterpene, FR65814 1 is described. The cyclohexane ring in 1 was prepared in an optically active form from D-glucose using Ferrier's carbocyclization reaction, and the carbon side-chain in 1 was stereoselectively introduced via chirality transfer by way of Claisen rearrangement of the cyclohexenol derivative, followed by Pd- catalyzed Stille coupling. The bis-epoxide function was stereoselectively constructed by sulfur ylide chemistry and vanadium catalyzed epoxidation of a homoallyl alcohol derivative. This first total synthesis fully confirmed the proposed absolute structure of FR65814.

Total synthesis and absolute configuration of FR65814

The chiral and highly stereoselective synthesis of FR658141, a novel immunosuppressant, starting from D-glucose is described; this first total synthesis fully confirms the proposed structure of 1.