136051-63-3

Basic information

• Product Name: nortrilobolide
• Synonyms: nortrilobolide
• CAS NO: 136051-63-3
• Molecular Formula: C₂₆H₃₆O₁₀
• Molecular Weight: 508.55804
• Mol File: 136051-63-3.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 596.5°Cat760mmHg
• Flash Point: 190.6°C
• Appearance: /
• Density: 1.29g/cm³
• Vapor Pressure: 1.02E-16mmHg at 25°C
• Refractive Index: 1.551
• CAS DataBase Reference: nortrilobolide(CAS DataBase Reference)
• NIST Chemistry Reference: nortrilobolide(136051-63-3)
• EPA Substance Registry System: nortrilobolide(136051-63-3)

Safety Data

• Hazardous Substances Data: 136051-63-3(Hazardous Substances Data)

Usage

InChI:InChI=1/C26H36O10/c1-8-10-19(28)34-18-12-24(6,36-15(5)27)16-11-17(33-22(29)13(3)9-2)14(4)20(16)21-26(18,32)25(7,31)23(30)35-21/h9,16-18,21,31-32H,8,10-12H2,1-7H3/b13-9-/t16-,17+,18?,21-,24+,25+,26+/m0/s1

Upstream product

• 106-31-0 butanoic acid anhydride 
• 105612-28-0 (3S,3aR,4S,6S,6aS,8R,9bS)-6-(acetyloxy)-3,3a,4-trihydroxy-3,6,9-trimethyl-2-oxo-2,3,3a,4,5,6,6a,7,8,9b-decahydroazuleno[4,5-b]furan-8-yl (2Z)-2-methylbut-2-enoate 
• 565-63-9 Angelic acid 
• 898831-15-7 (4aR,7S,8S)-8-Hydroxy-7-isopropenyl-1,4a-dimethyl-5,6,7,8-tetrahydro-4aH-naphthalen-2-one 
• 94487-74-8 (Z)-2-methyl-2-butenoic anhydride 
• 282551-65-9 6α-hydroxy-7-epi-α-cyperone 
• 898831-32-8 (R)-7-((S)-1,2-Dihydroxy-1-methyl-ethyl)-1,4a-dimethyl-5,6-dihydro-4aH-naphthalen-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 

Downstream Products

• 123269-03-4 thiapsigargin 

Relevant articles and documents

METHOD FOR PREPARATION OF INTERMEDIATES USEFUL FOR PREPARATION OF THAPSIGARGIN AND NORTRILOBOLIDE

The present invention relates to the preparation of Thapsigargin (1) and Nortrilobolide (2). The invention further relates to intermediates and preparation of said intermediates which are useful for the preparation of (1) and (2).

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.