247200-05-1

Basic information

• Product Name: Toluene-4-sulfonic acid (E)-(1S,2R)-1-[(3R,4R)-7-benzyloxy-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-heptyl]-2-methoxymethoxy-dodec-3-enyl ester
• Synonyms: Toluene-4-sulfonic acid (E)-(1S,2R)-1-[(3R,4R)-7-benzyloxy-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-heptyl]-2-methoxymethoxy-dodec-3-enyl ester
• CAS NO: 247200-05-1
• Molecular Weight: 863.4
• Mol File: 247200-05-1.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: Toluene-4-sulfonic acid (E)-(1S,2R)-1-[(3R,4R)-7-benzyloxy-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-heptyl]-2-methoxymethoxy-dodec-3-enyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Toluene-4-sulfonic acid (E)-(1S,2R)-1-[(3R,4R)-7-benzyloxy-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-heptyl]-2-methoxymethoxy-dodec-3-enyl ester(247200-05-1)
• EPA Substance Registry System: Toluene-4-sulfonic acid (E)-(1S,2R)-1-[(3R,4R)-7-benzyloxy-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-heptyl]-2-methoxymethoxy-dodec-3-enyl ester(247200-05-1)

Safety Data

• Hazardous Substances Data: 247200-05-1(Hazardous Substances Data)

Upstream product

• 204572-66-7 (4R,5R)-8-Benzyloxy-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-octanal 
• 98-59-9 p-toluenesulfonyl chloride 
• 247200-04-0 (E)-(4R,5R,8S,9R)-1-Benzyloxy-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-9-methoxymethoxy-nonadec-10-en-8-ol 

Downstream Products

• 102989-24-2 (+)-asimicin 
• 156162-01-5 asimin 
• 247200-07-3 Toluene-4-sulfonic acid (1S,2R)-1-[(3R,4R)-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-7-oxo-heptyl]-2-methoxymethoxy-dodecyl ester 
• 507480-62-8 Toluene-4-sulfonic acid (E)-(1S,4R,5R,8S,9R)-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-8-hydroxy-9-methoxymethoxy-1-((R)-1-methoxymethoxy-undecyl)-hexadec-10-en-15-ynyl ester 
• 507480-63-9 C₅₇H₉₈O₁₂S₂Si₂ 
• 507480-66-2 Toluene-4-sulfonic acid (E)-(1S,4R,5R,8S,9R,14S)-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-14-(tert-butyl-diphenyl-silanyloxy)-8-hydroxy-9-methoxymethoxy-1-((R)-1-methoxymethoxy-undecyl)-hexadec-10-en-15-ynyl ester 
• 507480-67-3 (E,11R,12S,15R,16R,19S,20R)-15,16-di(tert-butyldimethylsilyloxy)-25-(tert-butyldiphenylsilyloxy)-11,20-di(methoxymethoxy)-12,19-di(p-toluenesulfonoxy)-21-heptacosen-26-yne 
• 247200-10-8 C₆₂H₁₀₄O₁₃S₂Si₂ 
• 247200-09-5 Toluene-4-sulfonic acid (E)-(1S,4R,5R,8S,9R)-14-benzyloxy-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-8-hydroxy-9-methoxymethoxy-1-((R)-1-methoxymethoxy-undecyl)-tetradec-10-enyl ester 
• 247200-11-9 (2R,5R,2'R,5'R)-5-((E)-(R)-6-Benzyloxy-1-methoxymethoxy-hex-2-enyl)-5'-((R)-1-methoxymethoxy-undecyl)-octahydro-[2,2']bifuranyl 
• 247200-06-2 Toluene-4-sulfonic acid (1S,2R)-1-[(3R,4R)-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-7-hydroxy-heptyl]-2-methoxymethoxy-dodecyl ester 

Relevant articles and documents

Total synthesis of the cytotoxic threo, trans, threo, trans, threo annonaceous acetogenin asimin and its C-10 epimer: Unambiguous confirmation of absolute stereochemistry

A convergent synthesis of asimin (1) and its C-10 epimer 33 is reported. The essential features of this synthesis include (a) the addition of an enantioenriched γ-OMOM allylic indium reagent to a core C-23 aldehyde precursor to install the C-24-C-34 segment with concomitant introduction of the C-24 and C-23 stereocenters; (b) the addition of an enantioenriched γ- OMOM allylic indium reagent to a core C-16 aldehyde to install the C-10-C-15 segment with formation of the C-15 and C-16 stereocenters, (c) the addition of a dialkyl zinc reagent, catalyzed by a Chiral triflamide-Ti(O-i-Pr)4 complex, to introduce the C-1-C-9 segment with creation of either the 10(R) or 10(S) stereocenters; and (d) aldol condensation of the foregoing C-1-C-34 segment with OTBS-protected lactic aldehyde to incorporate the C-35-C-37 butenolide segment. Removal of the three MOM protecting groups was achieved with aqueous HCl in THF. The 10(R) diastereomer was found to correspond to natural asimin.