350580-88-0

Basic information

• Product Name: Methanesulfonic acid (S)-2-(tert-butyl-dimethyl-silanyloxy)-1-[(2aS,3R,6R,7aS,7bR)-2,2-diisopropyl-6-((1S,2R)-2-phenyl-cyclohexyloxy)-hexahydro-1,4,5-trioxa-4a-aza-2-sila-cyclopenta[cd]inden-3-yl]-ethyl ester
• Synonyms: Methanesulfonic acid (S)-2-(tert-butyl-dimethyl-silanyloxy)-1-[(2aS,3R,6R,7aS,7bR)-2,2-diisopropyl-6-((1S,2R)-2-phenyl-cyclohexyloxy)-hexahydro-1,4,5-trioxa-4a-aza-2-sila-cyclopenta[cd]inden-3-yl]-ethyl ester
• CAS NO: 350580-88-0
• Molecular Weight: 684.054
• Mol File: 350580-88-0.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: Methanesulfonic acid (S)-2-(tert-butyl-dimethyl-silanyloxy)-1-[(2aS,3R,6R,7aS,7bR)-2,2-diisopropyl-6-((1S,2R)-2-phenyl-cyclohexyloxy)-hexahydro-1,4,5-trioxa-4a-aza-2-sila-cyclopenta[cd]inden-3-yl]-ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Methanesulfonic acid (S)-2-(tert-butyl-dimethyl-silanyloxy)-1-[(2aS,3R,6R,7aS,7bR)-2,2-diisopropyl-6-((1S,2R)-2-phenyl-cyclohexyloxy)-hexahydro-1,4,5-trioxa-4a-aza-2-sila-cyclopenta[cd]inden-3-yl]-ethyl ester(350580-88-0)
• EPA Substance Registry System: Methanesulfonic acid (S)-2-(tert-butyl-dimethyl-silanyloxy)-1-[(2aS,3R,6R,7aS,7bR)-2,2-diisopropyl-6-((1S,2R)-2-phenyl-cyclohexyloxy)-hexahydro-1,4,5-trioxa-4a-aza-2-sila-cyclopenta[cd]inden-3-yl]-ethyl ester(350580-88-0)

Safety Data

• Hazardous Substances Data: 350580-88-0(Hazardous Substances Data)

Upstream product

• 350580-97-1 [2aS,3R(1S),6R(1S,2R),7aS,7bR]-hexahydro-2,2-bis(1-methylethyl)-3-(S)-[2-[((1,1-dimethylethyl)dimethylsilyl)oxy]-1-hydroxyethyl]-6-[(2-phenylcyclohexyl)oxy]-2H-1,4,5-trioxy-4a-aza-2-silacyclopent[cd]indene 
• 7143-01-3 Methanesulfonic anhydride 
• 69739-34-0 t-butyldimethylsiyl triflate 

Downstream Products

• 34281-92-0 (1S,2R)-trans-2-phenyl-1-cyclohexanol 

Relevant articles and documents

Synthesis of (+)-1-epiaustraline

A highly efficient total synthesis of (+)-1-epiaustraline ((+)-1), a tetrahydroxypyrrolizidine alkaloid of the alexine/australine subclass, is described. The key step is a tandem intramolecular [4 + 2]/intermolecular [3 + 2] nitroalkene cycloaddition involving dienylsilyloxy nitroalkene 3 and chiral vinyl ether 4, which establishes four of the five stereocenters present. The final center was installed by a diastereoselective dihydroxylation. Hydrogenolytic unmasking of the nitroso acetal tosylate 17 containing the silyl ether linkage was thwarted by a slow alkylation and an undesired Peterson-type elimination. Prior removal of the silicon moiety by Tamao-Fleming oxidation proceeded in excellent yield and provided a substrate suitable for hydrogenolysis and deprotection. The complete synthesis required only 10 steps to deliver the (+)-1-epiaustraline in 7.0% overall yield.