101915-87-1

Basic information

• Product Name: 6,7-(Z)-N-PMB-15-OMe-Latrunculin B
• Synonyms: 6,7-(Z)-N-PMB-15-OMe-Latrunculin B
• CAS NO: 101915-87-1
• Molecular Weight: 529.698
• Mol File: 101915-87-1.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: 6,7-(Z)-N-PMB-15-OMe-Latrunculin B(CAS DataBase Reference)
• NIST Chemistry Reference: 6,7-(Z)-N-PMB-15-OMe-Latrunculin B(101915-87-1)
• EPA Substance Registry System: 6,7-(Z)-N-PMB-15-OMe-Latrunculin B(101915-87-1)

Safety Data

• Hazardous Substances Data: 101915-87-1(Hazardous Substances Data)

Upstream product

• 2436-90-0 (S)-(+)-dihydromyrcene 
• 1056194-62-7 (Z)-((2R,4R,6R)-2-methoxy-2-((R)-3-(4-methoxybenzyl)-2-oxothiazolidin-4-yl)-6-((S)-3-methylpent-4-enyl)-tetrahydro-2H-pyran-4-yl)-3-methylhepta-2,6-dienoate 
• 139944-42-6 (S)-4-{(2R,4S,6R)-4,6-Dihydroxy-6-[(R)-3-(4-methoxy-benzyl)-2-oxo-thiazolidin-4-yl]-tetrahydro-pyran-2-yl}-2-methyl-butyric acid (1R,2R)-2-hydroxy-1-methyl-propyl ester 
• 101860-56-4 (R)-4-[3-Hydroxy-4-((2R,3R,7R,10S)-2,3,10-trimethyl-1,4,6-trioxa-spiro[4.5]dec-7-yl)-butyryl]-3-(4-methoxy-benzyl)-thiazolidin-2-one 
• 140146-99-2 (S)-4-{(2R,4S,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-6-methoxy-6-[(R)-3-(4-methoxy-benzyl)-2-oxo-thiazolidin-4-yl]-tetrahydro-pyran-2-yl}-2-methyl-butyric acid (1R,2R)-2-(tert-butyl-dimethyl-silanyloxy)-1-methyl-propyl ester 
• 139944-35-7 (S)-4-{(2R,4S,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-6-methoxy-6-[(R)-3-(4-methoxy-benzyl)-2-oxo-thiazolidin-4-yl]-tetrahydro-pyran-2-yl}-2-methyl-butyraldehyde 
• 140146-97-0 (S)-4-{(2R,4S,6R)-4-Hydroxy-6-methoxy-6-[(R)-3-(4-methoxy-benzyl)-2-oxo-thiazolidin-4-yl]-tetrahydro-pyran-2-yl}-2-methyl-butyric acid (1R,2R)-2-hydroxy-1-methyl-propyl ester 
• 139944-43-7 (R)-4-[(2R,4S,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-6-((S)-4-hydroxy-3-methyl-butyl)-2-methoxy-tetrahydro-pyran-2-yl]-3-(4-methoxy-benzyl)-thiazolidin-2-one 
• 101860-61-1 (2Z,6Z)-(S)-10-{(2R,4S,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-6-methoxy-6-[(R)-3-(4-methoxy-benzyl)-2-oxo-thiazolidin-4-yl]-tetrahydro-pyran-2-yl}-3,8-dimethyl-deca-2,6-dienoic acid 
• 139944-44-8 (Z)-6-Iodo-3-methyl-hex-2-enoic acid 
• 51804-12-7 Methyl 6-chloro-2-hexynoate 
• 107408-69-5 6-chloro-3-methyl-2-hexanoic acid 
• 53840-30-5 (Z)-methyl 3-methyl-6-chloro-2-hexenoate 
• 14267-92-6 1-chloro-4-pentyne 

Downstream Products

• 76343-94-7 latrunculin B 
• 1114568-09-0 6,7-(Z)-N-PMB-Latrunculin B 
• 105917-28-0 6,7-(Z)-15-OMe-Latrunculin B 

Relevant articles and documents

Examination of the olefin-olefin ring closing metathesis to prepare Latrunculin B

Three subunits of the potent actin polymerization inhibitor Latrunculin B were synthesized and assembled using olefin-olefin ring closing metathesis chemistry to close the 14-membered macrocycle. Metathesis reactions of substrates with various remote protecting group patterns were examined and gave 6,7-E-lactones as the preferred products.

Cytoskeletal active compounds, compositions and use

The present invention is directed to synthetic cytoskeletal active compounds that are related to natural Latrunculin A or Latrunculin B. The present invention is also directed to pharmaceutical compositions comprising such compounds and a pharmaceutically

Total synthesis of the latrunculins

The total syntheses of (+)-latrunculin A (1) and (+)-latrunculin B (2), two architecturally novel toxins isolated from the Red Sea sponge Latrunculia magnifica (Keller), have been achieved via highly convergent and stereocontrolled routes (longest linear sequences, 16 and 12 steps, respectively). Formal syntheses of scalemic latrunculins C (3) and M (5) also derive from the construction of 2. Central features of the unified synthetic strategy include the aldol reaction of aldehyde (-)-12 with methyl ketone (-)-13, a novel acid-catalyzed reorganization-equilibration of ortho ester (-)-11, and Mitsunobu macrolide cyclization.