920018-52-6

Basic information

• Product Name: 4,8-Dioxa-3,9-disilaundecane, 9,9-diethyl-2,2-dimethyl-3,3-diphenyl-7-(2-propyn-1-yl)-, (7R)-
• CAS NO: 920018-52-6
• Molecular Formula: C28H42O2Si2
• Molecular Weight: 466.811
• Mol File: 920018-52-6.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: 4,8-Dioxa-3,9-disilaundecane, 9,9-diethyl-2,2-dimethyl-3,3-diphenyl-7-(2-propyn-1-yl)-, (7R)-(CAS DataBase Reference)
• NIST Chemistry Reference: 4,8-Dioxa-3,9-disilaundecane, 9,9-diethyl-2,2-dimethyl-3,3-diphenyl-7-(2-propyn-1-yl)-, (7R)-(920018-52-6)
• EPA Substance Registry System: 4,8-Dioxa-3,9-disilaundecane, 9,9-diethyl-2,2-dimethyl-3,3-diphenyl-7-(2-propyn-1-yl)-, (7R)-(920018-52-6)

Safety Data

• Hazardous Substances Data: 920018-52-6(Hazardous Substances Data)

Upstream product

• 920018-51-5 (S)-5-(tert-butyldiphenylsilanyloxy)-3-(triethylsilanyloxy)pentanal 
• 90965-06-3 dimethyl 1-(1-diazo-2-oxopropyl)phosphonate 
• 920018-70-8 C₂₈H₄₄O₂Si₂ 
• 127047-71-6 3-(tert-butyldiphenylsilyloxy)propan-1-ol 
• 112897-09-3 (3R)-1-(tert-butyldiphenylsilyloxy)hex-5-en-3-ol 
• 112897-03-7 3-(tert-butyldiphenylsilyloxy)-1-propanal 
• 79271-56-0 triethylsilyl trifluoromethyl sulfonate 

Downstream Products

• 920018-53-7 (S)-5-bromo-1-(tert-butyl-diphenyl-silanyloxy)-hex-5-en-3-ol 
• 920018-73-1 C₂₈H₄₃BrO₂Si₂ 
• 920034-32-8 (R)-8-(tert-butyldiphenylsilanyloxy)-1-((2R,4R,6R)-4-(tert-butyldiphenylsilanyloxy)-6-(2-(chloromethyl)oxazol-4-yl)tetrahydro-2H-pyran-2-yl)-4-methylene-6-(triethylsilanyloxy)octan-2-ol 
• 920018-72-0 (R)-9,9-diethyl-2,2-dimethyl-3,3-diphenyl-7-(prop-2-ynyl)-4,8-dioxa-3,9-disilaundecane 

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%.