657389-53-2

Basic information

• Product Name: (2R,3R,4R,5R,6S)-2-(2-oxoethyl)-6-((S)-1-tert-butyldimethylsilanyloxyethyl)-4-(4-methoxy-benzyloxy)-3,5-dimethyltetrahydropyran
• Synonyms: (2R,3R,4R,5R,6S)-2-(2-oxoethyl)-6-((S)-1-tert-butyldimethylsilanyloxyethyl)-4-(4-methoxy-benzyloxy)-3,5-dimethyltetrahydropyran
• CAS NO: 657389-53-2
• Molecular Weight: 450.691
• Mol File: 657389-53-2.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (2R,3R,4R,5R,6S)-2-(2-oxoethyl)-6-((S)-1-tert-butyldimethylsilanyloxyethyl)-4-(4-methoxy-benzyloxy)-3,5-dimethyltetrahydropyran(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3R,4R,5R,6S)-2-(2-oxoethyl)-6-((S)-1-tert-butyldimethylsilanyloxyethyl)-4-(4-methoxy-benzyloxy)-3,5-dimethyltetrahydropyran(657389-53-2)
• EPA Substance Registry System: (2R,3R,4R,5R,6S)-2-(2-oxoethyl)-6-((S)-1-tert-butyldimethylsilanyloxyethyl)-4-(4-methoxy-benzyloxy)-3,5-dimethyltetrahydropyran(657389-53-2)

Safety Data

• Hazardous Substances Data: 657389-53-2(Hazardous Substances Data)

Upstream product

• 657389-88-3 (2R,3R,4R,5R,6S)-2-allyl-6-((S)-1-tert-butyldimethylsilanyloxyethyl)-4-(4-methoxy-benzyloxy)-3,5-dimethyltetrahydropyran 
• 657389-52-1 (2R,3R,4R,5R,6S)-2-allyl-6-((S)-1-hydroxyethyl)-4-(4-methoxy-benzyloxy)-3,5-dimethyltetrahydropyran 
• 69739-34-0 t-butyldimethylsiyl triflate 

Downstream Products

• 657389-95-2 2-{6-[6-(2-{3-[6-[1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-(4-methoxy-benzyloxy)-3,5-dimethyl-tetrahydro-pyran-2-yl]-propenyl}-oxazol-4-yl)-4-triisopropylsilanyloxy-tetrahydro-pyran-2-ylmethyl]-4-methylene-tetrahydro-pyran-2-yl}-ethanol 
• 552850-11-0 C₅₅H₉₀BrNO₁₁Si₂ 
• 552850-01-8 C₅₃H₈₄BrNO₁₀Si₂ 
• 552850-00-7 6-[9-bromo-1-(tert-butyl-dimethyl-silanyloxy)-6-methoxy-3-methyl-nona-2,4,8-trienyl]-2-(4-{2-[6-(2,2-dimethoxy-ethyl)-4-(4-methoxy-benzyloxy)-3,5-dimethyl-tetrahydro-pyran-2-yl]-propenyl}-oxazol-2-ylmethyl)-4-methoxy-tetrahydro-pyran-2-ol 
• 552849-99-7 4-{(E)-2-[(2R,3R,4S,5S,6R)-6-(2,2-Dimethoxy-ethyl)-4-(4-methoxy-benzyloxy)-3,5-dimethyl-tetrahydro-pyran-2-yl]-propenyl}-2-methyl-oxazole 
• 552849-97-5 (2R,3R,4R,5R,6R)-2-(2-dimethoxyethylacetal)-6-(1-oxoethyl)-4-(4-methoxy-benzyloxy)-3,5-dimethyltetrahydropyran 
• 657389-66-7 C₅₇H₉₅NO₁₀Si₂ 
• 657389-54-3 (S)-1-[(2R,3R,4S,5S,6R)-6-(2,2-Dimethoxy-ethyl)-4-(4-methoxy-benzyloxy)-3,5-dimethyl-tetrahydro-pyran-2-yl]-ethanol 

Relevant articles and documents

Total synthesis of (+)-phorboxazole A, a potent cytostatic agent from the sponge Phorbas sp.

A convergent total synthesis of phorboxazole A (1a), from the C(3-19), C(20-27) and C(33-46) fragments 5, 4 and 91, respectively, concentrating on stereocontrolled formation of the bonds at C(2-3), C(19-20) and C(27-28), is described. Although a coupling reaction between a macrolide ketone and the side chain substituted sulfone, at C(27-28) was not successful, a Wadsworth-Emmons olefination involving the oxane methyl ketone 4 and an oxazole produced the oxane 90 which was next coupled to 91 leading to the C(20-46) unit 100. A further coupling of 100 to 71c at C(19-20) then led to 105, ultimately, and the synthesis was completed by a macrocyclisation reaction from 105, at the C(2-3) alkene bond, followed by deprotection of 106.