71908-06-0

Basic information

• Product Name: erythro-S-(1,1-dimethylethyl) 3-hydroxy-2-methyl-3-phenylpropanethioate
• CAS NO: 71908-06-0
• Molecular Weight: 252.378
• Mol File: 71908-06-0.mol

Chemical Properties

• CAS DataBase Reference: erythro-S-(1,1-dimethylethyl) 3-hydroxy-2-methyl-3-phenylpropanethioate(CAS DataBase Reference)
• NIST Chemistry Reference: erythro-S-(1,1-dimethylethyl) 3-hydroxy-2-methyl-3-phenylpropanethioate(71908-06-0)
• EPA Substance Registry System: erythro-S-(1,1-dimethylethyl) 3-hydroxy-2-methyl-3-phenylpropanethioate(71908-06-0)

Safety Data

• Hazardous Substances Data: 71908-06-0(Hazardous Substances Data)

Upstream product

• 1247747-90-5 S-t-butylphenyl α-iodothiopropionate 
• 100-52-7 benzaldehyde 
• 97250-85-6 2-((Z)-1-tert-Butylsulfanyl-propenyloxy)-[1,3,2]dioxaborolane 
• 76943-94-7 (Z)-1-(tert-butylthio)-1-trimethylsilyloxyprop-1-ene 
• 76943-95-8 (E)-1-(tert-butylthio)-1-trimethylsilyloxyprop-1-ene 
• 61540-13-4 tert-butyl thiopropionate 
• 6004-44-0 prop-1-en-1-one 
• 75-66-1 2-methylpropan-2-thiol 
• 120425-01-6 (Z/E)-1-tert-butylthio-1-trimethylsililoxy-1-propene 
• 102146-11-2 1-tert-butylthio-1-(tert-butyldimethylsilyloxy)prop-1-ene 
• 97250-84-5 tert-Butyl-((E)-1-tert-butylsulfanyl-propenyloxy)-dimethyl-silane 
• 43143-00-6 C₁₂H₂₇BS 

Relevant articles and documents

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A mild method for the diastereoselective Mukaiyama aldol reaction is reported. By using a low loading of the gallium(III) triflate catalyst (down to 0.01 mol-%), the transformation proceeds efficiently to afford the corresponding β-hydroxy ketones in yields up to 92a€‰%. To the best of our knowledge, this is the first report of a metal triflate acting as a safe, bench-stable, and slow-releasing source of triflic acid for the Mukaiyama aldol reaction. A diastereoselective Mukaiyama aldol reaction was performed under mild conditions with a low loading of the gallium(III) triflate catalyst (down to 0.01 mol-%). The transformation proceeded efficiently to afford the corresponding β-hydroxy ketones in yields up to 92a€‰%. Copyright

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Method for Performing Aldol Reaction in Water

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O-(Silacyclobutyl) ketene acetals derived from esters, thiol esters, and amides underwent facile aldol addition with a variety of aldehydes at room temperature without the need for catalysts. The uncatalyzed aldol addition reaction of O-(silacyclobutyl) ketene acetals displayed the following characteristics: (1) the rate of reaction was highly dependent on the spectator substituent on silicon and the geometry of the ketene acetal, (2) the O,O-ketene acetal of E configuration afforded the syn aldol products with high diastereoselectivity (93/7 to 99/1), (3) conjugated aldehydes reacted more rapidly than aliphatic aldehydes, and (4) the reaction was mildly sensitive to solvent. In addition, the aldol reaction was found to be efficiently catalyzed by metal alkoxides. Labeling experiments revealed that the thermal aldol reaction proceeds by direct intramolecular silicon group transfer, while the alkoxide-catalyzed version probably proceeds via in situ generated metal enolates. Computational modeling of the transition states suggests that the boat transition structures are preferred, supporting the observed syn selectivity of the thermal aldol reaction. Both thermal and alkoxide-catalyzed Michael additions were investigated, revealing a competition between 1,2- and 1,4-addition favoring the former.

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