Next Article in Journal
2-{[(4-Hydroxy-3,5-dimethoxyphenyl)methylidene]hydrazinylidene}-4-oxo-1,3-thiazolidin-5-yl Acetic Acid
Previous Article in Journal
N-[2-(1H-Indol-3-yl)-1-(5-thioxo-4,5-dihydro-1,3,4-oxadiazol-2-yl)ethyl]-4-methylbenzenesulfonamide
Communication

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
*
Author to whom correspondence should be addressed.
Molbank 2018, 2018(3), M1010; https://doi.org/10.3390/M1010
Received: 6 July 2018 / Revised: 22 July 2018 / Accepted: 24 July 2018 / Published: 29 July 2018
(This article belongs to the Section Organic Synthesis)
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
Show Figures

Figure 1

MDPI and ACS Style

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. https://doi.org/10.3390/M1010

AMA Style

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(3):M1010. https://doi.org/10.3390/M1010

Chicago/Turabian Style

Sasaki, Ryosuke, Momoyo Kawamoto, and Yoo Tanabe. 2018. "Benzyl (R)-2-(Acetylthio)Propanoate: A Promising Sulfur Isoster of (R)-Lactic Acid and Ester Precursors" Molbank 2018, no. 3: M1010. https://doi.org/10.3390/M1010

Find Other Styles
Note that from the first issue of 2016, MDPI journals use article numbers instead of page numbers. See further details here.

Article Access Map by Country/Region

1
Back to TopTop