1352577-42-4

Basic information

• Product Name: (5S)-3-(2-((1S,4R,5S,6S,7R)-4-(tert-butyldimethylsilyloxy)-1-methyl-7-((1E,3E)-3-methylpenta-1,3-dienyl)-8-oxabicyclo[3.2.1]octan-6-yl)-1-hydroxyethyl)-5-isobutyl-1-(phenylcarbonyl)pyrrolidin-2-one
• Synonyms: (5S)-3-(2-((1S,4R,5S,6S,7R)-4-(tert-butyldimethylsilyloxy)-1-methyl-7-((1E,3E)-3-methylpenta-1,3-dienyl)-8-oxabicyclo[3.2.1]octan-6-yl)-1-hydroxyethyl)-5-isobutyl-1-(phenylcarbonyl)pyrrolidin-2-one
• CAS NO: 1352577-42-4
• Molecular Weight: 623.949
• Mol File: 1352577-42-4.mol

Chemical Properties

• CAS DataBase Reference: (5S)-3-(2-((1S,4R,5S,6S,7R)-4-(tert-butyldimethylsilyloxy)-1-methyl-7-((1E,3E)-3-methylpenta-1,3-dienyl)-8-oxabicyclo[3.2.1]octan-6-yl)-1-hydroxyethyl)-5-isobutyl-1-(phenylcarbonyl)pyrrolidin-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: (5S)-3-(2-((1S,4R,5S,6S,7R)-4-(tert-butyldimethylsilyloxy)-1-methyl-7-((1E,3E)-3-methylpenta-1,3-dienyl)-8-oxabicyclo[3.2.1]octan-6-yl)-1-hydroxyethyl)-5-isobutyl-1-(phenylcarbonyl)pyrrolidin-2-one(1352577-42-4)
• EPA Substance Registry System: (5S)-3-(2-((1S,4R,5S,6S,7R)-4-(tert-butyldimethylsilyloxy)-1-methyl-7-((1E,3E)-3-methylpenta-1,3-dienyl)-8-oxabicyclo[3.2.1]octan-6-yl)-1-hydroxyethyl)-5-isobutyl-1-(phenylcarbonyl)pyrrolidin-2-one(1352577-42-4)

Safety Data

• Hazardous Substances Data: 1352577-42-4(Hazardous Substances Data)

Upstream product

• 197006-11-4 (R)-tert-butyl 2-isobutyl-5-oxopyrrolidine-1-carboxylate 
• 98-88-4 benzoyl chloride 
• 1352577-35-5 (1S,2R,5S,6S,7S)-2-(tert-butyldimethylsilyloxy)-7-(2-hydroxyethyl)-5-methyl-8-oxabicyclo[3.2.1]octane-6-carbaldehyde 
• 1352577-33-3 (1S,2R,5S,6S,7S)-2-(tert-butyldimethylsilyloxy)-7-(2-(tert-butyldiphenylsilyloxy)ethyl)-5-methyl-8-oxabicyclo[3.2.1]octane-6-carbaldehyde 
• 1352577-32-2 (S,Z)-5-((2S,5R,6R)-5-(tert-butyldimethylsilyloxy)-6-methoxy-2-methyltetrahydro-2H-pyran-2-yl)-2,2,3,3,12,12-hexamethyl-11,11-diphenyl-4,10-dioxa-3,11-disilatridec-6-ene 
• 1352577-47-9 (S)-5-((2S,5R,6R)-5-(tert-butyldimethylsilyloxy)-6-methoxy-2-methyltetrahydro-2H-pyran-2-yl)-2,2,3,3,12,12-hexamethyl-11,11-diphenyl-4,10-dioxa-3,11-disilatridec-6-yne 
• 1352577-31-1 (S)-1-(2S,5R,6R-5-(tert-butyldimethylsilyloxy)-6-methoxy-2-methyltetrahydro-2H-pyran-2-yl)-5-(tert-butyldiphenylsilyloxy)pent-2-yn-1-ol 
• 1352577-41-3 2-((1S,4R,5S,6S,7R)-4-(tert-butyldimethylsilyloxy)-1-methyl-7-((1E,3E)-3-methylpenta-1,3-dienyl)-8-oxabicyclo[3.2.1]octan-6-yl)ethanal 
• 124575-36-6 (5R)-1-benzoyl-5-(2-methylpropyl)pyrrolidin-2-one 
• 1352577-50-4 2-((1S,4R,5S,6S,7R)-4-(tert-butyldimethylsilyloxy)-1-methyl-7-((1E,3E)-3-methylpenta-1,3-dienyl)-8-oxabicyclo[3.2.1]octan-6-yl)ethanol 
• 1352577-40-2 tert-butyl((2-(1S,4R,5S,6S,7R)-4-(tert-butyldimethylsilyloxy)-1-methyl-7-((1E,3E)-3-methylpenta-1,3-dienyl)-8-oxabicyclo[3.2.1]octan-6-yl)ethoxy)diphenylsilane 
• 1352577-39-9 tert-butyl((2-(1S,4R,5S,6S,7S)-4-(tert-butyldimethylsilyloxy)-7-((E)-2-iodovinyl)-1-methyl-8-oxabicyclo[3.2.1]octan-6-yl)ethoxy)diphenylsilane 
• 1352577-34-4 (1S,2R,5S,6R,7S)-2-(tert-butyldimethylsilyloxy)-7-(2-(tert-butyldiphenylsilyloxy)ethyl)-5-methyl-8-oxabicyclo[3.2.1]octane-6-carbaldehyde 
• 1352577-38-8 ((1S,2R,5S,6S,7S)-2-(tert-butyldimethylsilyloxy)-7-(2-(tert-butyldiphenylsilyloxy)ethyl)-5-methyl-8-oxabicyclo[3.2.1]octan-6-yl)methanol 

Downstream Products

• 1352577-43-5 (5S)-3-(2-((1S,4R,5S,6S,7R)-4-(tert-butyldimethylsilyloxy)-1-methyl-7-((1E,3E)-3-methylpenta-1,3-dienyl)-8-oxabicyclo[3.2.1]octan-6-yl)ethanoyl)-5-isobutyl-1-(phenylcarbonyl)pyrrolidin-2-one 
• 1352577-44-6 (5S)-3-(2-((1S,4R,5S,6S,7R)-4-(tert-butyldimethylsilyloxy)-1-methyl-7-((1E,3E)-3-methylpenta-1,3-dienyl)-8-oxabicyclo[3.2.1]octan-6-yl)ethanoyl)-5-isobutyl-1-(phenylcarbonyl)-3-(phenylselanyl)pyrrolidin-2-one 
• 1352577-45-7 N-benzoyl-O-tert-butyldimethylsilyl-aspergillin PZ 

Relevant articles and documents

Identification of an unexpected 2-oxonia[3,3]sigmatropic rearrangement/aldol pathway in the formation of oxacyclic rings. Total synthesis of (+)-aspergillin PZ

This paper reports the first unambiguous evidence that the cascade synthesis of tetrahydrofuran-containing oxacyclic molecules depicted in Scheme 12 can take place by a 2-oxonia[3,3]sigmatropic/aldol mechanism rather than by a Prins cyclization/pinacol rearrangement sequence. The 8-oxabicyclo[3.2.1]octyl aldehyde products of this reaction, 20 and 29, were employed to complete the first total synthesis of the structurally remarkable isoindolone alkaloid (+)-aspergillin PZ (1). The lack of activity seen in two tumor cell lines for synthetic (+)-aspergillin PZ calls into question the suggestion that aspergillin PZ, like many aspochalasin diterpenes, might exhibit useful antitumor properties.