2003
DOI: 10.1248/cpb.51.448
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Application of Modified Mosher's Method for Primary Alcohols with a Methyl Group at C2 Position.

Abstract: Modified Mosher's method using a-methoxy-a-trifluoromethylphenylacetyl (MTPA) esters has been recognized as a useful and reliable method for determination of absolute configurations of secondary alcohols and primary amines. [1][2][3] The absolute configurations at such methine carbons could be determined by the regular arrangement: positive and negative chemical shift differences [Dd(d S Ϫd R )] of the protons can be found on the right and left sides of the MTPA plane, respectively. Nevertheless, it is difficu… Show more

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Cited by 41 publications
(27 citation statements)
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“…52 The absolute configuration of the 3-position in 1,3-dihydroxy ketones can be assigned on the basis of its MTPA derivative. In this case, it is possible to almost exclusively derivatize the primary hydroxyl group and use data from known compounds to assign the configuration of the unknown.…”
Section: Primary Alcoholsmentioning
confidence: 99%
“…52 The absolute configuration of the 3-position in 1,3-dihydroxy ketones can be assigned on the basis of its MTPA derivative. In this case, it is possible to almost exclusively derivatize the primary hydroxyl group and use data from known compounds to assign the configuration of the unknown.…”
Section: Primary Alcoholsmentioning
confidence: 99%
“…On the other hand, the major isomer of (S)-MTPA ester (S)-2 (64:36 ratio) indicated overlapping methylene signals both for H-1 (d 4.34, Dd = 0) and Table 1). 7 Since the opposite phenomenon was observed for the oxymethylene protons (H-16) of (R)-2 (Dd = 0.17) and (S)-2 (Dd = 0.03) (Table 1), the (15R)-configuration of a1 1 was determined.…”
Section: Resultsmentioning
confidence: 98%
“…The mixture was allowed to stand at room temperature for 30 min, diluted with pyridine-d 5 (400 ml), and the 1 H-NMR spectrum was recorded. The spectrum showed complete formation of the (R)-MTPA ester (5) 6 Hz, H-7, Me-6).…”
Section: Extraction and Isolationmentioning
confidence: 99%
“…Hydrolysis of 7 and 8 afforded 2(S)-and 2(R)-2, 7) respectively, the absolute configuration of which was confirmed by the MTPA method: (R)-MTPA ester (9) of 2(S)-2 shows an overlapped AB pattern of H 2 -1, while (R)-MTPA ester (10) of 2(R)-2 shows a well-separated AB pattern (Experimental). Interestingly, the 6 Hz, Me-6). These chemical shifts are the same with those of the methyl protons of (1R,2R)-2ACyclo-COOH ester of 6(S)-methyloctan-1-ol, 10) leading to the 6(S)-configuration of 3.…”
mentioning
confidence: 98%
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