663606-00-6

Basic information

• Product Name: (2aS,5aS,7S,7aS,9S,10R,10aR,10bS,10cR)-9-(tert-Butyl-diphenyl-silanyloxy)-7,10c-dihydroxy-2a,4,4,7,10-pentamethyl-decahydro-1,3,5-trioxa-benzo[cd]cyclopenta[h]azulen-2-one
• Synonyms: (2aS,5aS,7S,7aS,9S,10R,10aR,10bS,10cR)-9-(tert-Butyl-diphenyl-silanyloxy)-7,10c-dihydroxy-2a,4,4,7,10-pentamethyl-decahydro-1,3,5-trioxa-benzo[cd]cyclopenta[h]azulen-2-one
• CAS NO: 663606-00-6
• Molecular Weight: 594.821
• Mol File: 663606-00-6.mol

Chemical Properties

• CAS DataBase Reference: (2aS,5aS,7S,7aS,9S,10R,10aR,10bS,10cR)-9-(tert-Butyl-diphenyl-silanyloxy)-7,10c-dihydroxy-2a,4,4,7,10-pentamethyl-decahydro-1,3,5-trioxa-benzo[cd]cyclopenta[h]azulen-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: (2aS,5aS,7S,7aS,9S,10R,10aR,10bS,10cR)-9-(tert-Butyl-diphenyl-silanyloxy)-7,10c-dihydroxy-2a,4,4,7,10-pentamethyl-decahydro-1,3,5-trioxa-benzo[cd]cyclopenta[h]azulen-2-one(663606-00-6)
• EPA Substance Registry System: (2aS,5aS,7S,7aS,9S,10R,10aR,10bS,10cR)-9-(tert-Butyl-diphenyl-silanyloxy)-7,10c-dihydroxy-2a,4,4,7,10-pentamethyl-decahydro-1,3,5-trioxa-benzo[cd]cyclopenta[h]azulen-2-one(663606-00-6)

Safety Data

• Hazardous Substances Data: 663606-00-6(Hazardous Substances Data)

Upstream product

• 77-76-9 2,2-dimethoxy-propane 
• 663605-99-0 (3S,3aR,4S,6S,6aS,8S,9R,9aR,9bS)-8-(tert-Butyl-diphenyl-silanyloxy)-3,3a-dihydroxy-4,6-bis-methoxymethoxy-3,6,9-trimethyl-decahydro-azuleno[4,5-b]furan-2-one 
• 950849-16-8 C₃₁H₄₂O₇Si 
• 2244-16-8 (S)-p-mentha-6,8-dien-2-one 
• 950849-15-7 2-(Diethoxy-phosphoryl)-propionic acid (1R,2S,3aS,4S,6S,8S,8aR)-2-(tert-butyl-diphenyl-silanyloxy)-4-methoxymethoxy-1,4-dimethyl-7-oxo-8-triethylsilanyloxy-decahydro-azulen-6-yl ester 
• 663605-88-7 tert-Butyl-[(1S,2R,3R,4S)-3-(4-methoxy-benzyloxymethyl)-4-(1-methoxymethoxy-1-methyl-but-3-enyl)-2-methyl-cyclopentyloxy]-diphenyl-silane 
• 663606-10-8 2-[(1S,2R,3R,4S)-4-(tert-Butyl-diphenyl-silanyloxy)-2-(4-methoxy-benzyloxymethyl)-3-methyl-cyclopentyl]-pent-4-en-2-ol 
• 663605-86-5 tert-Butyl-[(1S,2R,3S,4S)-4-isopropenyl-3-(4-methoxy-benzyloxymethyl)-2-methyl-cyclopentyloxy]-diphenyl-silane 
• 663605-87-6 1-[(1S,2R,3R,4S)-4-(tert-Butyl-diphenyl-silanyloxy)-2-(4-methoxy-benzyloxymethyl)-3-methyl-cyclopentyl]-ethanone 
• 663605-89-8 [(1R,2R,3S,5S)-3-(tert-Butyl-diphenyl-silanyloxy)-5-((S)-1-methoxymethoxy-1-methyl-but-3-enyl)-2-methyl-cyclopentyl]-methanol 
• 663606-11-9 (1R,2R,3S,5S)-3-(tert-Butyl-diphenyl-silanyloxy)-5-((S)-1-methoxymethoxy-1-methyl-but-3-enyl)-2-methyl-cyclopentanecarbaldehyde 
• 663605-85-4 (1S,2R,3S,5S)-3-(tert-Butyl-diphenyl-silanyloxy)-5-isopropenyl-2-methyl-cyclopentanecarboxylic acid methyl ester 
• 950849-05-5 [(1S,2R,3S,5S)-3-(tert-Butyl-diphenyl-silanyloxy)-5-isopropenyl-2-methyl-cyclopentyl]-methanol 
• 663606-09-5 methyl (1S,2R,3S,5S)-3-hydroxy-5-isopropenyl-2-methylcyclopentanecarboxylate 

Downstream Products

• 930280-05-0 C₃₆H₆₀O₉SeSi₃ 
• 123269-03-4 thiapsigargin 
• 50657-07-3 trilobolide 
• 136051-63-3 nortrilobolide 

Relevant articles and documents

Total synthesis of five thapsigargins: Guaianolide natural products exhibiting sub-nanomolar SERCA inhibition

Herein we describe the total synthesis of five guaianolide natural products: thapsigargin. thapsivillosin C, thapsivillosin F, trilobolide and nortrilobolide. Prodrug derivatives of thapsigargin have shown selective in vivo cytotoxicity against prostate tumours and the need for further investigation of this phenomenon highlights the importance of these total syntheses. The first absolute stereochemical assignment of thapsivillosin C is also delineated.

A Route to the Thapsigargins from (S)-Carvone Providing a Substrate-Controlled Total Synthesis of Trilobolide, Nortrilobolide, and Thapsivillosin F

An entirely substrate-controlled total synthesis of three members of the thapsigargin family (e.g. trilobolide) is achieved starting from (S)-carvone. The synthesis is linear in nature but is achieved in high yield (> 90% per step). The route permits late