187527-29-3

Basic information

• Product Name: [(S)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2,2-dimethyl-pentyloxymethyl]-benzene
• Synonyms: [(S)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2,2-dimethyl-pentyloxymethyl]-benzene
• CAS NO: 187527-29-3
• Molecular Weight: 466.852
• Mol File: 187527-29-3.mol

Chemical Properties

• CAS DataBase Reference: [(S)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2,2-dimethyl-pentyloxymethyl]-benzene(CAS DataBase Reference)
• NIST Chemistry Reference: [(S)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2,2-dimethyl-pentyloxymethyl]-benzene(187527-29-3)
• EPA Substance Registry System: [(S)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2,2-dimethyl-pentyloxymethyl]-benzene(187527-29-3)

Safety Data

• Hazardous Substances Data: 187527-29-3(Hazardous Substances Data)

Upstream product

• 121352-86-1 ethyl (E)-5-(benzyloxy)-4,4-dimethylpent-2-enoate 
• 126-30-7 2,2-Dimethyl-1,3-propanediol 
• 100-44-7 benzyl chloride 
• 121352-88-3 [(2R,3R)-3-(2-Benzyloxy-1,1-dimethyl-ethyl)-oxiranyl]-methanol 
• 121352-87-2 (E)-5-(benzyloxy)-4,4-dimethylpent-2-en-1-ol 
• 38216-93-2 3-benzyloxypivalic aldehyde 
• 66582-32-9 3-(benzyloxy)-2,2-dimethylpropan-1-ol 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 152426-81-8 (3S)-1-benzyloxy-2,2-dimethylpentane-3,5-diol 

Downstream Products

• 297135-61-6 (6R,7S,10R)-4-[(2S,4S)-5-[2-((2S,6R)-6-Benzyloxymethyl-4,4-dimethoxy-tetrahydro-pyran-2-ylmethyl)-[1,3]dithian-2-yl]-4-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-5-methyl-hexyl]-7-isopropyl-10-methyl-1,5-dioxa-spiro[5.5]undec-3-en-2-one 
• 152426-93-2 {(4R,6R)-6-[(S)-3-[2-((2S,6R)-6-Benzyloxymethyl-4-oxo-tetrahydro-pyran-2-ylmethyl)-[1,3]dithian-2-yl]-2-(tert-butyl-dimethyl-silanyloxy)-3-methyl-butyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-acetic acid ethyl ester 
• 152426-92-1 (5S,7S)-8-[2-((2S,6R)-6-Benzyloxymethyl-4,4-dimethoxy-tetrahydro-pyran-2-ylmethyl)-[1,3]dithian-2-yl]-7-(tert-butyl-dimethyl-silanyloxy)-5-hydroxy-8-methyl-3-oxo-nonanoic acid ethyl ester 
• 152426-88-5 (2R,6S)-2-Benzyloxymethyl-6-{2-[(S)-2,4-bis-(tert-butyl-dimethyl-silanyloxy)-1,1-dimethyl-butyl]-[1,3]dithian-2-ylmethyl}-4,4-dimethoxy-tetrahydro-pyran 
• 152426-90-9 (S)-4-[2-((2S,6R)-6-Benzyloxymethyl-4,4-dimethoxy-tetrahydro-pyran-2-ylmethyl)-[1,3]dithian-2-yl]-3-(tert-butyl-dimethyl-silanyloxy)-4-methyl-pentanal 
• 152426-89-6 (S)-4-[2-((2S,6R)-6-Benzyloxymethyl-4,4-dimethoxy-tetrahydro-pyran-2-ylmethyl)-[1,3]dithian-2-yl]-3-(tert-butyl-dimethyl-silanyloxy)-4-methyl-pentan-1-ol 
• 187527-24-8 (2S,3S,4R,7S)-1-benzyloxy-7,9-bis(tert-butyldimethylsilyloxy)-3-hydroxy-2,4,6,6-tetramethylnonan-5-one 
• 187527-27-1 (3S,6R,7S,8S)-9-benzyloxy-1,3,7-trihydroxy-4,4,6,8-tetramethylnonan-5-one 
• 187527-25-9 (-)-(5S)-5,7-bis{[tert-butyl(dimethyl)silyl]oxy}-4,4-dimethylheptan-3-one 

Relevant articles and documents

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.

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.

Synthetic studies on bryostatins, antineoplastic metabolites: Convergent synthesis of the C1-C16 fragment shared by all of the bryostatin family

The C1-C16 fragment of bryostatins could successfully be synthesized by tandem connection of the appropriate three fragments and effective introduction of the α,β-unsaturated esters at the C13 position.