219606-79-8

Basic information

• Product Name: 2,7-Octadienoic acid, 5-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-6-methyl-8-phenyl-, 1,1-dimethylethyl ester, (2E,5S,6R,7E)-
• CAS NO: 219606-79-8
• Molecular Formula: C25H40O3Si
• Molecular Weight: 416.676
• Mol File: 219606-79-8.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: 2,7-Octadienoic acid, 5-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-6-methyl-8-phenyl-, 1,1-dimethylethyl ester, (2E,5S,6R,7E)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2,7-Octadienoic acid, 5-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-6-methyl-8-phenyl-, 1,1-dimethylethyl ester, (2E,5S,6R,7E)-(219606-79-8)
• EPA Substance Registry System: 2,7-Octadienoic acid, 5-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-6-methyl-8-phenyl-, 1,1-dimethylethyl ester, (2E,5S,6R,7E)-(219606-79-8)

Safety Data

• Hazardous Substances Data: 219606-79-8(Hazardous Substances Data)

Upstream product

• 849619-01-8 1-(4-methoxybenzyloxy)-4-methylhex-5-en-3-ol 
• 69739-34-0 t-butyldimethylsiyl triflate 
• 219606-75-4 tert-butyl (5S,6R)-5-tert-butyldimethylsilanyloxy-7-(4-methoxybenzyloxy)-6-methylhept-2(E)-enoate 
• 219606-74-3 (3S,4R)-3-tert-butyldimethylsilanyloxy-5-(4-methoxybenzyloxy)-4-methylpentanal 
• 219606-73-2 tert-Butyl-{(S)-1-[(R)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-but-3-enyloxy}-dimethyl-silane 
• 219606-76-5 tert-butyl (5S,6R)-5-tert-butyldimethylsilanyloxy-7-hydroxy-6-methylhept-2(E)-enoate 
• 219606-77-6 tert-butyl (5S,6S)-5-tert-butyldimethylsilanyloxy-6-methyl-7-oxohept-2(E)-enoate 
• 219606-81-2 (3R,4S)-4,6-bis(tert-butyldimethylsilyloxy)-3-methylhex-1-ene 
• 203926-55-0 (2R,3S)-1-[(4-methoxyphenyl)methoxy]-2-methyl-5-hexen-3-ol 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 168777-81-9 (3S,4R)-1-[(tert-butyldimethylsilyl)oxy]-4-methylhex-5-en-3-ol 
• 86302-43-4 (tert-Butoxycarbonylmethylene)triphenylphosphorane 
• 220249-56-9 tert-butyl(((3S,4R)-1-((4-methoxybenzyl)oxy)-4-methylhex-5-en-3-yl)oxy)dimethylsilane 
• 220249-55-8 (3S,4R)-1-(4-methoxybenzyloxy)-4-(trifluoromethyl)hex-5-en-3-ol 

Downstream Products

• 155645-51-5 Cryptophycin 4 
• 162600-54-6 cryptophycin-24 
• 162600-54-6 arenastatin A 
• 124689-65-2 cryptophycin-1 
• 182486-25-5 tert-butyl (5S,6R)-5-[(2S)-2-[(2R)-3-[(2R)-2-tert-butoxycarbonylamino-3-(3-chloro-4-methoxyphenyl)propionylamino]-2-methylpropionyloxy]-4-methylpentanoyloxy]-6-methyl-8-phenylocta-2(E),7(E)-dienoate 
• 245125-92-2 tert-butyl (5S,6R)-5-[(2S)-2-[(2R)-3-[(2R)-2-tert-butoxycarbonylamino-3-(4-methoxyphenyl)-propionylamino]-2-methylpropionyloxy]-4-methylpentanoyloxy]-6-methyl-8-phenylocta-2(E),7(E)-dienoate 
• 245125-91-1 tert-butyl (5S,6R)-5-[(2S)-2-[3-[(2R)-2-(tert-butoxycarbonylamino)-3-(3-chloro-4-methoxyphenyl)propionylamino]propionyloxy]-4-methylpentanoyloxy]-6-methyl-8-phenylocta-2(E),-7(E)-dienoate 
• 162600-54-6 arenastatin A 
• 162600-54-6 (E)-(3S,10R,16S)-3-Isobutyl-10-(4-methoxy-benzyl)-16-[(S)-1-((2S,3R)-3-phenyl-oxiranyl)-ethyl]-1,4-dioxa-8,11-diaza-cyclohexadec-13-ene-2,5,9,12-tetraone 
• 162600-54-6 cryptophycin-24 
• 219606-86-7 tert-butyl (5S,6R)-5-[(2S)-2-[3-[(2R)-2-tert-butoxycarbonylamino-3-(4-methoxyphenyl)-propionylamino]propionyloxy]-4-methylpentanoyloxy]-6-methyl-8-phenylocta-2(E),7(E)-dienoate 
• 162473-78-1 desepoxyarenastatin A 
• 848044-28-0 tert-butyl (2E,5S,6R,7E)-5-[(2S)-2-{[(2R)-3-({3-chloro-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-O-methyl-D-tyrosyl}amino)-2-methylpropanoyl]oxy}-4-methylpentanoyloxy]-6-methyl-8-phenylocta-2,7-dienoate 
• 1027041-92-4 (2E,7E)-(5S,6R)-5-((S)-2-{(R)-3-[(R)-3-(3-Chloro-4-methoxy-phenyl)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionylamino]-2-methyl-propionyloxy}-4-methyl-pentanoyloxy)-6-methyl-8-phenyl-octa-2,7-dienoic acid 

Relevant articles and documents

Enantioselective synthesis of a 3'-dephenylcryptophycin synthon

An enantioselective synthesis of tert-butyl (5S,6R)-(E)-5-tert- butyldimethylsilyloxy-6-methyl-2,7-octadienoate, a precursor for the synthesis of the antimitotic macrolides cryptophycin A and arenastatin A (cryptophycin-24), is presented. The key step in the reaction sequence features a crotyl boration that sets both stereocenters that become the C16 hydroxyl and C1' methyl in the cryptophycins. Homologation of the terminal olefin via a Heck reaction is presented.

Synthesis of cryptothilone 1, the first cryptophycin-epothilone hybrid

A hybrid structure was synthesized in which one portion is characteristic of a cryptophycin and a second sector bears the signature of an epothilone. The hybrid, in contrast to parent cryptophycin and epothilone systems, showed no effect on the tubulin as

Total synthesis of cryptophycin-24 (arenastatin A) amenable to structural modifications in the C16 side chain

Two efficient protocols for the synthesis of tert-butyl (5S,6R,2E,7E)-5-[(tert-butyldimethylsilyl)-oxy]-6-methyl-8-phenyl-2,7-octadie noate, a major component of the cryptophycins, are reported. The first utilized the Noyori reduction and Frater alkylation of methyl 5-benzyloxy-3-oxopentanoate to set two stereogenic centers, which became the C16 hydroxyl and C1' methyl of the cryptophycins. The second approach started from 3-p-methoxybenzyloxypropanal and a crotyl borane reagent derived from (-)-α-pinene to set both stereocenters in a single step and provided the dephenyl analogue, tert-butyl (5S,6R,2E)-5-[(tert-butyldimethylsilyl)oxy]-6-methyl-2,7-octadienoate, in five steps. This compound was readily converted to the 8-phenyl compound via Heck coupling. The silanyloxy esters were efficiently deprotected and coupled to the C2-C10 amino acid fragment to provide desepoxyarenastatin A and its dephenyl analogue. The terminal olefin of the latter was further elaborated via Heck coupling. Epoxidation provided cryptophycin-24 (arenastatin A).