189246-61-5

Basic information

• Product Name: Silane, (1,1-dimethylethyl)[[(1S,2E)-9-(2-hexyl-1,3-dioxolan-2-yl)-1-[(1S)-2-[(4- methoxyphenyl)diphenylmethoxy]-1-(phenylmethoxy)ethyl]-2-nonenyl]oxy ]dimethyl-
• CAS NO: 189246-61-5
• Molecular Formula: C53H74O6Si
• Molecular Weight: 835.252
• Mol File: 189246-61-5.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: Silane, (1,1-dimethylethyl)[[(1S,2E)-9-(2-hexyl-1,3-dioxolan-2-yl)-1-[(1S)-2-[(4- methoxyphenyl)diphenylmethoxy]-1-(phenylmethoxy)ethyl]-2-nonenyl]oxy ]dimethyl-(CAS DataBase Reference)
• NIST Chemistry Reference: Silane, (1,1-dimethylethyl)[[(1S,2E)-9-(2-hexyl-1,3-dioxolan-2-yl)-1-[(1S)-2-[(4- methoxyphenyl)diphenylmethoxy]-1-(phenylmethoxy)ethyl]-2-nonenyl]oxy ]dimethyl-(189246-61-5)
• EPA Substance Registry System: Silane, (1,1-dimethylethyl)[[(1S,2E)-9-(2-hexyl-1,3-dioxolan-2-yl)-1-[(1S)-2-[(4- methoxyphenyl)diphenylmethoxy]-1-(phenylmethoxy)ethyl]-2-nonenyl]oxy ]dimethyl-(189246-61-5)

Safety Data

• Hazardous Substances Data: 189246-61-5(Hazardous Substances Data)

Upstream product

• 189246-53-5 1-bromo-7-methoxymethoxytridecane 
• 189246-54-6 (7RS)-1-bromo-7-tridecanol 
• 111-71-7 heptanal 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 189246-60-4 (16S,17S)-17-benzyloxy-16,18-dihydroxyoctadec-14-yne-7-one ethylene acetal 
• 181495-46-5 (4R,5R)-5-benzyloxy-4-(2-trimethylsilylethynyl)-2,2-dimethyl-1,3-dioxane 
• 181434-88-8 (2S,3S)-2-benzyloxy-5-trimethylsilylpent-4-yne-1,3-diol 
• 181434-87-7 phenyl (2R,3S)-2-benzyloxy-3-hydroxy-5-trimethylsilylpent-4-ynoate 
• 189246-56-8 (4R,5S,9'RS)-5-benzyloxy-2,2-dimethyl-4-(9'-trimethylsiloxypentadec-1'-ynyl)-1,3-dioxane 
• 189246-58-0 (4S,5S)-5-benzyloxy-2,2-dimethyl-4-(9'-oxopentadec-1'-ynyl)-1,3-dioxane 
• 189246-57-9 (4S,5S,9'RS)-5-benzyloxy-2,2-dimethyl-4-(9'-trimethylsiloxypentadec-1'-ynyl)-1,3-dioxane 
• 189246-59-1 (16S,17S)-17-benzyloxy-16,18-dihydroxyoctadec-14-yne-7-one 
• 181434-86-6 (4S,5S)-5-benzyloxy-4-ethynyl-2,2-dimethyl-1,3-dioxane 
• 189246-52-4 (3RS)-ethyl-3-hydroxynonanethioate 

Downstream Products

• 145401-48-5 sphingofungin F 
• 189246-63-7 (2R,3S)-2-benzyloxy-3-(tert-butyldimethylsiloxy)-12-oxooctadec-4-enal 
• 189246-66-0 (2S,3S,4R,5S)-2-amino-4-benzyloxy-2-methyl-3,5-dihydroxy-14-oxoeicos-6-enoic acid 
• 189246-65-9 (1'S,4'S,16S,17S,18R)-17-benzyloxy-18-(3',6'-diethoxy-1',4'-dimethyl-4'H-2',5'-diazyl)-16,18-dihydroxyoctadec-14-ene-7-one 
• 189246-64-8 (1'S,4'S,16S,17S,18R)-17-benzyloxy-16-(tert-butyldimethylsiloxy)-18-(3',6'-diethoxy-1',4'-dimethyl-4'H-2',5'-diazyl)-18-hydroxyoctadec-14-ene-7-one 
• 189246-62-6 (16S,17S)-17-benzyloxy-16-(tert-butyldimethylsiloxy)-18-hydroxyoctadec-14-ene-7-one 

Relevant articles and documents

Catalytic asymmetric syntheses of antifungal sphingofungins and their biological activity as potent inhibitors of serine palmitoyltransferase (SPT)

Unambiguous synthetic routes to sphingofungins B and F and to their stereoisomers have been developed based on the tin(II)-catalyzed asymmetric aldol reaction (Chiral Lewis Acid-Controlled Synthesis (CLAC Synthesis)). Efficient enantioselective synthesis using a catalytic amount of a chiral source as well as the effectiveness of this strategy for the synthesis of the sphingofungin family have been successfully demonstrated. Using the stereoisomers of sphingofungin B synthesized, the relevance of its stereochemistry to its SPT inhibitory activity has been revealed.

The Asymmetric Synthesis of Sphingofungin F and the Determination of Its Stereochemistry

The asymmetric synthesis of sphingofungin F has been achieved and its stereochemistry has been determined. Its structure, including the absolute configuration of the chiral centers, was found to be similar to that of sphingofungin B or myriocin. The synth