381665-45-8

Basic information

• Product Name: 2H-Pyran-2-one, 6-[(1E,3R,4R,6R,7Z,9Z,11E)-6-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-13 -[[(1,1-dimethylethyl)diphenylsilyl]oxy]-4-hydroxy-3-methyl-3-[(triethylsilyl) oxy]-1,7,9,11-tridecatetraenyl]-5,6-dihydro-, (6R)-
• CAS NO: 381665-45-8
• Molecular Formula: C47H72O6Si3
• Molecular Weight: 817.342
• Mol File: 381665-45-8.mol
• Article Data: 9

Chemical Properties

• CAS DataBase Reference: 2H-Pyran-2-one, 6-[(1E,3R,4R,6R,7Z,9Z,11E)-6-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-13 -[[(1,1-dimethylethyl)diphenylsilyl]oxy]-4-hydroxy-3-methyl-3-[(triethylsilyl) oxy]-1,7,9,11-tridecatetraenyl]-5,6-dihydro-, (6R)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2H-Pyran-2-one, 6-[(1E,3R,4R,6R,7Z,9Z,11E)-6-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-13 -[[(1,1-dimethylethyl)diphenylsilyl]oxy]-4-hydroxy-3-methyl-3-[(triethylsilyl) oxy]-1,7,9,11-tridecatetraenyl]-5,6-dihydro-, (6R)-(381665-45-8)
• EPA Substance Registry System: 2H-Pyran-2-one, 6-[(1E,3R,4R,6R,7Z,9Z,11E)-6-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-13 -[[(1,1-dimethylethyl)diphenylsilyl]oxy]-4-hydroxy-3-methyl-3-[(triethylsilyl) oxy]-1,7,9,11-tridecatetraenyl]-5,6-dihydro-, (6R)-(381665-45-8)

Safety Data

• Hazardous Substances Data: 381665-45-8(Hazardous Substances Data)

Upstream product

• 149401-42-3 (E)-5-(benzyloxy)pent-3-en-2-one 
• 381665-44-7 (6R)-6-[(1E,3R,4R,6R,7Z)-6-{[tert-butyl(dimethyl)silyl]oxy}-4-hydroxy-8-iodo-3-methyl-3-[(triethylsilyl)oxy]octa-1,7-dien-1-yl]-5,6-dihydro-2H-pyran-2-one 
• 1242069-85-7 (R)-5,6-dihydro-6-((1E,3R,4R,6R,7Z,9Z,11E)-3-triethylsilyloxy-6-tert-butyldimethylsilyloxy-4,13-dihydroxy-3-methyltrideca-1,7,9,11-tetraenyl)pyran-2-one 
• 58479-61-1 tert-butylchlorodiphenylsilane 
• 411242-07-4 2-[(1'Z,3'E)-5'-(tert-butyldiphenylsilyloxy)penta-1',3'-dien-1'-yl]-4,4,5,5-tetramethyl-[1,3,2]-dioxaborolane 
• 381665-52-7 (R)-6-[(E)-(3R,4R,6R)-6-(tert-Butyl-dimethyl-silanyloxy)-4-(4-methoxy-benzyloxy)-3-methyl-3-triethylsilanyloxy-8-trimethylsilanyl-oct-1-en-7-ynyl]-5,6-dihydro-pyran-2-one 
• 381665-53-8 (R)-6-[(E)-(3R,4R,6R)-6-(tert-Butyl-dimethyl-silanyloxy)-8-iodo-4-(4-methoxy-benzyloxy)-3-methyl-3-triethylsilanyloxy-oct-1-en-7-ynyl]-5,6-dihydro-pyran-2-one 
• 381665-43-6 (R)-6-[(E)-(3R,4R,6R)-6-Hydroxy-4-(4-methoxy-benzyloxy)-3-methyl-3-triethylsilanyloxy-8-trimethylsilanyl-oct-1-en-7-ynyl]-5,6-dihydro-pyran-2-one 
• 381665-42-5 (R)-6-[(E)-(3R,4R)-4-(4-Methoxy-benzyloxy)-3-methyl-6-oxo-3-triethylsilanyloxy-8-trimethylsilanyl-oct-1-en-7-ynyl]-5,6-dihydro-pyran-2-one 
• 381665-50-5 (E)-(2R,3R)-5-((2R,6R)-6-Isopropoxy-3,6-dihydro-2H-pyran-2-yl)-3-methyl-3-triethylsilanyloxy-1-(2-trimethylsilanylethynyl-[1,3]dithian-2-yl)-pent-4-en-2-ol 
• 381665-41-4 (R)-6-[(E)-(3R,4R)-4-Hydroxy-3-methyl-3-triethylsilanyloxy-5-(2-trimethylsilanylethynyl-[1,3]dithian-2-yl)-pent-1-enyl]-5,6-dihydro-pyran-2-one 
• 381665-54-9 (R)-6-((3R,4R,6R,E)-6-(tert-butyldimethylsilyloxy)-4-hydroxy-8-iodo-3-methyl-3-(triethylsilyloxy)oct-1-en-7-ynyl)-5,6-dihydro-2H-pyran-2-one 
• 381665-51-6 (R)-6-((E)-(3R,4R)-4-Hydroxy-3-methyl-6-oxo-3-triethylsilanyloxy-8-trimethylsilanyl-oct-1-en-7-ynyl)-5,6-dihydro-pyran-2-one 
• 381665-49-2 Triethyl-[(E)-(R)-3-((2R,6R)-6-isopropoxy-3,6-dihydro-2H-pyran-2-yl)-1-methyl-1-(R)-oxiranyl-allyloxy]-silane 

Downstream Products

• 500702-54-5 diallyl (1R,3R,4Z,6Z,8E)-3-{[tert-butyl(dimethyl)silyl]oxy}-10-{[tert-butyl(diphenyl)silyl]oxy}-1-{(1R)-1-methyl-3-[(2R)-6-oxo-3,6-dihydro-2H-pyran-2-yl]-1-[(triethylsilyl)oxy]allyl}deca-4,6,8-trien-1-yl phosphate 
• 381665-55-0 Phosphoric acid mono-{(4Z,6Z,8E)-(1R,3R)-3-(tert-butyl-dimethyl-silanyloxy)-10-(tert-butyl-diphenyl-silanyloxy)-1-[(E)-(R)-1-methyl-3-((R)-6-oxo-3,6-dihydro-2H-pyran-2-yl)-1-triethylsilanyloxy-allyl]-deca-4,6,8-trienyl} ester 
• 87810-56-8 (+)-fostriecin 
• 445235-79-0 Phosphorous acid (4Z,6Z,8E)-(1R,3R)-3-(tert-butyl-dimethyl-silanyloxy)-10-(tert-butyl-diphenyl-silanyloxy)-1-[(E)-(R)-1-methyl-3-((R)-6-oxo-3,6-dihydro-2H-pyran-2-yl)-1-triethylsilanyloxy-allyl]-deca-4,6,8-trienyl ester bis-(4-methoxy-benzyl) ester 
• 575456-24-5 Phosphoric acid (4Z,6Z,8E)-(1R,3R)-3-(tert-butyl-dimethyl-silanyloxy)-10-(tert-butyl-diphenyl-silanyloxy)-1-[(E)-(R)-1-methyl-3-((R)-6-oxo-3,6-dihydro-2H-pyran-2-yl)-1-triethylsilanyloxy-allyl]-deca-4,6,8-trienyl ester bis-(4-methoxy-benzyl) ester 

Relevant articles and documents

Total synthesis of fostriecin (CI-920) via a convergent route

Fostriecin, a potent and promising antitumor antibiotic, was stereoselectively synthesized via a convergent route involving a three-segement coupling procedure.

Total synthesis of fostriecin: Via a regio-and stereoselective polyene hydration, oxidation, and hydroboration sequence

A total synthesis of the fostriecin has been achieved in 24 steps from enyne 11. The lactone moiety was installed by a Leighton allylation and Grubbs ring-closing metathesis reaction. The highly reactive Z,Z,E-triene moiety was installed via a late-stage Suzuki-Miyaura cross-coupling of a remarkably stable Z-vinyl boronate. The relative and absolute stereocenters of the C-8,9,11 triol were generated with a regio-and stereoselective asymmetric hydration/oxidation sequence.

Catalyst-controlled asymmetric synthesis of fostriecin and 8-epi-fostriecin

Catalytic asymmetric synthesis of the natural antibiotic fostriecin (CI-920) and its analogue 8-epi-fostriecin and evaluation of their biological activity are described. We used four catalytic asymmetric reactions to construct all of the chiral centers of