391208-74-5

Basic information

• Product Name: (1R,3R)-3-(tert-butyldiphenylsilanyloxy)-1-(2-((E)-3-((2R,3S,4S,5S,6R)-3,5-dimethyl-6-((E)-2-(2-methyloxazol-4-yl)prop-1-en-2-yl)-4-(triisopropylsilanyloxy)tetrahydro-2H-pyran-2-yl)prop-1-enyl)oxazol-4-yl)hex-5-en-1-ol
• Synonyms: (1R,3R)-3-(tert-butyldiphenylsilanyloxy)-1-(2-((E)-3-((2R,3S,4S,5S,6R)-3,5-dimethyl-6-((E)-2-(2-methyloxazol-4-yl)prop-1-en-2-yl)-4-(triisopropylsilanyloxy)tetrahydro-2H-pyran-2-yl)prop-1-enyl)oxazol-4-yl)hex-5-en-1-ol
• CAS NO: 391208-74-5
• Molecular Weight: 867.329
• Mol File: 391208-74-5.mol

Chemical Properties

• CAS DataBase Reference: (1R,3R)-3-(tert-butyldiphenylsilanyloxy)-1-(2-((E)-3-((2R,3S,4S,5S,6R)-3,5-dimethyl-6-((E)-2-(2-methyloxazol-4-yl)prop-1-en-2-yl)-4-(triisopropylsilanyloxy)tetrahydro-2H-pyran-2-yl)prop-1-enyl)oxazol-4-yl)hex-5-en-1-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,3R)-3-(tert-butyldiphenylsilanyloxy)-1-(2-((E)-3-((2R,3S,4S,5S,6R)-3,5-dimethyl-6-((E)-2-(2-methyloxazol-4-yl)prop-1-en-2-yl)-4-(triisopropylsilanyloxy)tetrahydro-2H-pyran-2-yl)prop-1-enyl)oxazol-4-yl)hex-5-en-1-ol(391208-74-5)
• EPA Substance Registry System: (1R,3R)-3-(tert-butyldiphenylsilanyloxy)-1-(2-((E)-3-((2R,3S,4S,5S,6R)-3,5-dimethyl-6-((E)-2-(2-methyloxazol-4-yl)prop-1-en-2-yl)-4-(triisopropylsilanyloxy)tetrahydro-2H-pyran-2-yl)prop-1-enyl)oxazol-4-yl)hex-5-en-1-ol(391208-74-5)

Safety Data

• Hazardous Substances Data: 391208-74-5(Hazardous Substances Data)

Upstream product

• 391208-70-1 (4R,6R)-6-(2-chloromethyloxazol-4-yl)-6-tert-butyldimethylsilanyloxy-4-hydroxyhex-1-ene 
• 391208-72-3 (4R),(6R)-6-(2-chloromethyloxazol-4-yl)-6-hydroxy-4-tert-butyldiphenylsilanyloxyhex-1-ene 
• 391208-65-4 (2R,3S,4S,5S,6R)-3,5-dimethyl-6-[(1E)-1-methyl-2-(2-methyloxazol-4-yl)vinyl]-4-triisopropylsilanyloxytetrahydropyran-2-ylethanol 
• 391208-71-2 (4R),(6R)-6-(2-chloromethyloxazol-4-yl)-6-tert-butyldimethylsilanyloxy-4-tert-butyldiphenylsilanyloxyhex-1-ene 
• 391208-62-1 4-[(3R),(4S),(5S),(6S),(1E)-3-(4-methoxybenzyloxy)-2,4,6-triisopropylsilanyloxyocta-1,7-dienyl]-2-methyloxazole 
• 391208-64-3 2-(2R,3S,4S,5S,6R)-3,5-dimethyl-6-[(1E)-1-methyl-2-(2-methyloxazol-4-yl)vinyl]-4-triisopropylsilanyloxytetrahydropyran-2-yl-acetic acid methyl ester 
• 391208-58-5 4-[(3R,4R,1E)-3-(4-methoxybenzyloxy)-2,4-dimethylhexa-1,5-dienyl]-2-methyloxazole 
• 391208-60-9 (2S,3R,4E)-3-(4-methoxybenzyloxy)-2,4-dimethyl-5-(2-methyloxazol-4-yl)pent-4-enal 
• 391208-68-7 (4R)-4-(chloromethyloxazol-4-yl)-4-tert-butyldimethylsilanyloxybut-1-ene 
• 391208-69-8 (3R)-3-(2-chloromethyloxazol-4-yl)-3-tert-butyldimethylsilanyloxypropanal 
• 391208-57-4 (3R),(4R),(1E)-2,4-dimethyl-1-(2-methyloxazol-4-yl)hexa-1,5-dien-3-ol 
• 391208-67-6 (3R)-3-(2-chloromethyloxazol-4-yl)-3-hydroxybut-1-ene 
• 154136-85-3 2-chloromethyloxazole-4-carboxaldehide 
• 208465-72-9 methyl 2-(chloromethyl)-1,3-oxazole-4-carboxylate 

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%.

Intramolecular palladium(II)-mediated alkoxy carbonylation as a route to functionalized tetrahydropyrans. synthesis of the C9-C32 segment of phorboxazole A

matrix presented Hydroxy alkene 12, synthesized stereoselectively from 2-methyloxazole-4-carboxaldehyde, underwent intramolecular methoxy carbonylation in the presence of palladium(II) acetate to give 13 in which all five stereogenic centers around the tetrahydropyran correspond to those in ring C of phorboxazole A. Aldehyde 15, derived from 13, was linked to hydroxy alkene 23 via a Wittig coupling, and the composite 25 was subjected to a second palladium(II) acetate mediated methoxy carbonylation to yield 26, accompanied by acetoxy ester 27.