1407517-57-0

Basic information

• Product Name: (2R,3R,4R,5E)-4-(4-methoxybenzyloxy)-3,5-dimethyl-6-(2-methyloxazol-4-yl)hex-5-ene-1,2-diol
• CAS NO: 1407517-57-0
• Molecular Weight: 361.438
• Mol File: 1407517-57-0.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (2R,3R,4R,5E)-4-(4-methoxybenzyloxy)-3,5-dimethyl-6-(2-methyloxazol-4-yl)hex-5-ene-1,2-diol(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3R,4R,5E)-4-(4-methoxybenzyloxy)-3,5-dimethyl-6-(2-methyloxazol-4-yl)hex-5-ene-1,2-diol(1407517-57-0)
• EPA Substance Registry System: (2R,3R,4R,5E)-4-(4-methoxybenzyloxy)-3,5-dimethyl-6-(2-methyloxazol-4-yl)hex-5-ene-1,2-diol(1407517-57-0)

Safety Data

• Hazardous Substances Data: 1407517-57-0(Hazardous Substances Data)

Upstream product

• 391208-58-5 4-[(3R,4R,1E)-3-(4-methoxybenzyloxy)-2,4-dimethylhexa-1,5-dienyl]-2-methyloxazole 
• 391208-57-4 (3R),(4R),(1E)-2,4-dimethyl-1-(2-methyloxazol-4-yl)hexa-1,5-dien-3-ol 
• 139630-91-4 (E)-2-methyl-3-(2-methyloxazol-4-yl)acrylaldehyde 
• 113732-84-6 2-methyl-1,3-oxazole-4-carbaldehyde 
• 85806-67-3 2-methyl-oxazole-4-carboxylic acid methyl ester 

Relevant articles and documents

Total synthesis of the marine toxin phorboxazole A using palladium(ii)-mediated intramolecular alkoxycarbonylation for tetrahydropyran synthesis

The potent antitumor agent phorboxazole A was synthesized from six subunits comprising C1-C2 (115), C3-C8 (98), C9-C19 (74), C20-C32 (52), C33-C41 (84) and C42-C46 (85). Tetrahydropyrans B and C containing cis-2,6-disubstitution were fabricated via palladium(ii)-mediated intramolecular alkoxycarbonylation which, in the case of tetrahydropyran C, was carried out with catalytic palladium(ii) and p-benzoquinone as the stoichiometric re-oxidant. Tetrahydropyran D was obtained by a stereoselective tin(iv)-catalyzed coupling of a C9 aldehyde with an allylsilane, and the C19-C20 connection was made using a completely stereoselective Wittig-Schlosser (E) olefination. Coupling of the oxazole C32 methyl substituent with the intact C33-C46 δ-lactone 3 was accompanied by elimination of the vinyl bromide to a terminal alkyne, but the C32-C33 linkage was implemented successfully with 83 and C33-C41 lactone 84. The C42-C46 segment of the side chain was then appended via Julia-Kocienski olefination. The macrolide portion of phorboxazole A was completed by means of an Ando-Still-Gennari intramolecular (Z)-selective olefination at C2-C3 which required placement of a (dimethoxyphosphinyl)acetate moiety at C24. Final deprotection led to phorboxazole A via a route in which the longest linear sequence is 37 steps and the overall yield is 0.36%.