222545-27-9

Basic information

• Product Name: (2S,3S,4S)-2-<(1E)-1,5-dimethylhexa-1,4-dien-1-yl>-1,2-di-(4-methoxybenzyl)oxy-cyclohexan-1-one
• CAS NO: 222545-27-9
• Molecular Weight: 478.629
• Mol File: 222545-27-9.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (2S,3S,4S)-2-<(1E)-1,5-dimethylhexa-1,4-dien-1-yl>-1,2-di-(4-methoxybenzyl)oxy-cyclohexan-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,3S,4S)-2-<(1E)-1,5-dimethylhexa-1,4-dien-1-yl>-1,2-di-(4-methoxybenzyl)oxy-cyclohexan-1-one(222545-27-9)
• EPA Substance Registry System: (2S,3S,4S)-2-<(1E)-1,5-dimethylhexa-1,4-dien-1-yl>-1,2-di-(4-methoxybenzyl)oxy-cyclohexan-1-one(222545-27-9)

Safety Data

• Hazardous Substances Data: 222545-27-9(Hazardous Substances Data)

Upstream product

• 222545-14-4 methyl 6-deoxy-6-iodo-2,3-di-O-(4-methoxy)benzyl-α-D-glucopyranoside 
• 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 
• 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 
• 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 
• 222545-21-3 (2E)-3-<(1S,2S,3S,6R)-6-(tert-butyldimethylsilyl)oxy-2,3-di-(4-methoxybenzyl)oxy-cyclohex-1-yl>but-2-en-1-ol 
• 222545-16-6 (1R,2S,5S,6S)-5,6-di-(4-methoxybenzyl)oxy-2-(tetrahydropyran-2-yl)oxy-cyclohex-3-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 
• 210765-03-0 (3R)-3-<(1S,2S,3S,6R)-6-(tert-butyldimethylsilyl)oxy-2,3-di-(4-methoxybenzyl)oxy-cyclohex-1-yl>butanal 
• 210764-96-8 (3S,4S,6R)-3,4-di-(4-methoxybenzyl)oxy-6-(tetrahydropyran-2-yl)oxy-cyclohex-1-ene 
• 210764-98-0 ethyl 2-<(1S,5S,6S)-5,6-di-(4-methoxybenzyl)oxy-cyclohex-2-en-1-yl>propionate 
• 222545-20-2 (1R,2R,3S,4S)-3-<(1R)-1-methylprop-2-en-1-yl>-4-(tert-butyldimethylsilyl)oxy-1,2-di-(4-methoxybenzyl)oxy-cyclohexane 
• 210764-92-4 methyl 4-O-acetyl-2,3-di-O-(4-methoxy)benzyl-α-D-xylo-hex-5-enopyranoside 

Relevant articles and documents

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.