6330-43-4

Usage

InChI:InChI=1/C8H16OS/c1-5-6-7(9)10-8(2,3)4/h5-6H2,1-4H3

Upstream product

• 75-66-1 2-methylpropan-2-thiol 
• 141-75-3 butyryl chloride 
• 115975-22-9 C₁₂H₁₃BrO₃ 
• 107-92-6 butyric acid 

Downstream Products

• 110361-95-0 3-tert-Butylsulfanylcarbonyl-2-((R)-1-phenyl-ethylamino)-pentanoic acid ethyl ester 

Relevant academic research and scientific papers

A Catalyst Designed for the Enantioselective Construction of Methyl- and Alkyl-Substituted Tertiary Stereocenters

Tertiary methyl-substituted stereocenters are present in numerous biologically active natural products. Reported herein is a catalytic enantioselective method for accessing these chiral building blocks using the Mukaiyama-Michael reaction between silyl ketene thioacetals and acrolein. To enable remote enantioface control on the nucleophile, a new iminium catalyst, optimized by three-parameter tuning and by identifying substituent effects on enantioselectivity, was designed. The catalytic process allows rapid access to chiral thioesters, amides, aldehydes, and ketones bearing an α-methyl stereocenter with excellent enantioselectivities, and allowed rapid access to the C4-C13 segment of (-)-bistramide A. DFT calculations rationalized the observed sense and level of enantioselectivity.

Synthesis of thiol esters by the reaction of ricinoleic acid with thiols under solvent-free conditions

The synthesis of several ricinoleic acid thiol esters starting from cis-(R)-12-hydroxyoctadec-9-enoic acid and thiols in the presence of N,N'-dicyclohexylcarbodiimide (DCC) is described. The method is efficient for aromatic and aliphatic thiols, selective

Total synthesis of (-)-ebelactone A and B

The β-lactone enzyme inhibitors (-)-ebelactone A (1) and (-)-ebelactone B (2) have been prepared in 12 steps from diethyl ketone (4 and 3% overall yield, respectively). The synthetic strategy adopted for the ebelactones demonstrates the use of reagent- and substrate-derived stereocontrol and requires the minimal use of protecting groups. The stereocenters at C2, C3, C8, C10, and C11 were constructed using boron aldol methodology. An asymmetric syn aldol addition of diethyl ketone to 2-ethylacrolein gave adduct 8 in 86% ee, followed by a diastereoselective syn aldol reaction to give 11. Subsequently, an Ireland-Claisen rearrangement was used to relay 1,2-syn into 1,5-syn relative stereochemistry, as in 12 → 14. In the anti aldol construction of the C2-C3 bond, the use of either a propionate or butyrate thioester enolate allowed for a divergent approach from aldehyde 17 to both (-)-ebelactone A and B. Several novel analogues of ebelactone A and B were also prepared with inverted stereochemistry at C2, C3, or C12.

Chelation-Controlled Enantioselective Synthesis of Key Intermediates for the Preparation of Carbapenem Antibiotics PS-5 and 1β-Methyl-PS-5

Reaction of the E silyl ketene acetal derived from (1S,2R)-N-methylephedrine butyrate (7) with TiCl4 and β-alkoxy aldehyde 5 gave the aldol product in 75percent yield as a 78:11:11 mixture of stereoisomers.In agreement with a chelated transition structure

ACTIVATION OF MIXED CARBOXILIC α-BROMOTOLUOYL ANHYDRIDES BY SILVER TETRAFLUOROBORATE. SYNTHESIS OF ESTERS AND THIOL ESTERS

Mixed carboxylic α-bromotoluoyl anhydrides were activated by silver tetrafluoroborate through intramolecular cyclization and reacted with alcohols or thiols giving the corresponding esters or thiol esters in good yields with the elimination of phtalide.

THE FACILE AND EFFICIENT PREPARATION OF PHENOLIC AND THIOL ESTERS

Phenolic and thiol esters are prepared efficiently in a facile process which involves heating the desired acyl halide and thiol or phenol as a neat mixture.Distillation after HX (X = Cl or Br) gas evolution ceases provides the title compounds in 75-96percent yields.