187527-24-8

Basic information

• Product Name: (2S,3S,4R,7S)-1-benzyloxy-7,9-bis(tert-butyldimethylsilyloxy)-3-hydroxy-2,4,6,6-tetramethylnonan-5-one
• Synonyms: (2S,3S,4R,7S)-1-benzyloxy-7,9-bis(tert-butyldimethylsilyloxy)-3-hydroxy-2,4,6,6-tetramethylnonan-5-one
• CAS NO: 187527-24-8
• Molecular Weight: 580.996
• Mol File: 187527-24-8.mol

Chemical Properties

• CAS DataBase Reference: (2S,3S,4R,7S)-1-benzyloxy-7,9-bis(tert-butyldimethylsilyloxy)-3-hydroxy-2,4,6,6-tetramethylnonan-5-one(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,3S,4R,7S)-1-benzyloxy-7,9-bis(tert-butyldimethylsilyloxy)-3-hydroxy-2,4,6,6-tetramethylnonan-5-one(187527-24-8)
• EPA Substance Registry System: (2S,3S,4R,7S)-1-benzyloxy-7,9-bis(tert-butyldimethylsilyloxy)-3-hydroxy-2,4,6,6-tetramethylnonan-5-one(187527-24-8)

Safety Data

• Hazardous Substances Data: 187527-24-8(Hazardous Substances Data)

Upstream product

• 79027-28-4 (2S)-3-(benzyloxy)-2-methylpropanal 
• 187527-25-9 (-)-(5S)-5,7-bis{[tert-butyl(dimethyl)silyl]oxy}-4,4-dimethylheptan-3-one 
• 121352-87-2 (E)-5-(benzyloxy)-4,4-dimethylpent-2-en-1-ol 
• 255398-79-9 (-)-(5S)-5,7-bis(tert-butyldimethylsilyloxy)-4,4-dimethylheptan-3-ol 
• 121352-86-1 ethyl (E)-5-(benzyloxy)-4,4-dimethylpent-2-enoate 
• 187527-29-3 [(S)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2,2-dimethyl-pentyloxymethyl]-benzene 
• 152426-82-9 (3S)-3,5-bis-(tert-butyldimethylsilyloxy)-2,2-dimethylpentanal 
• 187527-30-6 (3S)-3,5-bis{[tert-butyl(dimethyl)silyl]oxy}-2,2-dimethylpentan-1-ol 
• 152426-81-8 (3S)-1-benzyloxy-2,2-dimethylpentane-3,5-diol 
• 126-30-7 2,2-Dimethyl-1,3-propanediol 
• 121352-88-3 [(2R,3R)-3-(2-Benzyloxy-1,1-dimethyl-ethyl)-oxiranyl]-methanol 
• 38216-93-2 3-benzyloxypivalic aldehyde 
• 66582-32-9 3-(benzyloxy)-2,2-dimethylpropan-1-ol 

Downstream Products

• 187527-27-1 (3S,6R,7S,8S)-9-benzyloxy-1,3,7-trihydroxy-4,4,6,8-tetramethylnonan-5-one 

Relevant articles and documents

The formal total synthesis of epothilone A

The formal total synthesis of epothilone A is described. The key steps in the synthesis of the northern hemisphere are a Z-selective ten-membered ring-closing metathesis reaction (RCM) and the diastereoselective alkylation at C8. Aldehyde 3 is formed by introduction of the thiazole moiety by a Wittig reaction and subsequent functional group transformation. An efficient route to keto acid 5 is described.

Synthesis of the C1-C9 segment of epothilons

The C1-C9 segment of epothilons was generated by an aldol reaction between chiral aldehyde 3 and ethyl ketone 4. Removal of the TBS protecting groups and debenzylation generated spiro ketal 13 which was analyzed by X-ray crystallography.