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Molbank 2018, 2018(3), M1010; https://doi.org/10.3390/M1010

Benzyl (R)-2-(Acetylthio)Propanoate: A Promising Sulfur Isoster of (R)-Lactic Acid and Ester Precursors

Department of Chemistry, School of Science and Technology, Kwansei Gakuin University, 2-1 Gakuen, Sanda, Hyogo 669-1337, Japan
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Received: 6 July 2018 / Revised: 22 July 2018 / Accepted: 24 July 2018 / Published: 29 July 2018
(This article belongs to the Section Organic Synthesis)
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Abstract

In this paper, an accessible chiral pool synthesis of benzyl (R)-2-(acetylthio)propanoate (acetylthiolactate), which is less odorous than the methyl or ethyl analogue, was performed through a clean SN2 displacement reaction using available AcSK with tris[2-(2-methoxyethoxy)]ethylamine (TDA-1), starting from commercially available benzyl (S)-lactate in 76%, 94% ee (2 steps). Deprotection of the acetyl group using N,N-dimethylethylenediamine afforded benzyl (R)-2-sulfanylpropanoate in 93% yield with 90% ee. These two sulfur-containing benzyl esters were sufficiently odorless to be purified by column chromatography. Direct HPLC analysis was applied to determine the enantiomeric excess without thiazolidin-4-one derivatizations. A complementary debenzylation of benzyl (R)-2-(acetylthio)propanoate was also performed using HBr/AcOH to afford (R)-2-(acetylthio)propanoic acid without critical racemization in 92% yield with 92% ee. View Full-Text
Keywords: thiolactic ester; benzyl (S)-lactate; (R)-2-(acetylthio)propanoate; SN2 displacement; potassium thioacetate; benzyl (R)-2-sulfanylpropanoate; HPLC analysis; odorless thiolactic ester; benzyl (S)-lactate; (R)-2-(acetylthio)propanoate; SN2 displacement; potassium thioacetate; benzyl (R)-2-sulfanylpropanoate; HPLC analysis; odorless
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Sasaki, R.; Kawamoto, M.; Tanabe, Y. Benzyl (R)-2-(Acetylthio)Propanoate: A Promising Sulfur Isoster of (R)-Lactic Acid and Ester Precursors. Molbank 2018, 2018, M1010.

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