1994
DOI: 10.1021/jo00101a023
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Tetra-O-benzoylglucosylation: A New 1H Nuclear Magnetic Resonance Method for Determination of the Absolute Configuration of Secondary Alcohols

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Cited by 37 publications
(19 citation statements)
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“…The organic layer was dried over Na 2 SO 4 , and concentrated in vacuo. The residue was purified by silica gel column chromatography (n-hexane/EtOAc = 2:1) and preparative TLC ( (18). To a solution of 17 (67.0 mg, 96.1 mmol) in MeOH (1.0 ml) was added NaOMe (25.8 mg, 0.478 mmol) at 0 C, and the mixture was stirred for 4 h at rt under an argon atmosphere.…”
Section: Methodsmentioning
confidence: 99%
“…The organic layer was dried over Na 2 SO 4 , and concentrated in vacuo. The residue was purified by silica gel column chromatography (n-hexane/EtOAc = 2:1) and preparative TLC ( (18). To a solution of 17 (67.0 mg, 96.1 mmol) in MeOH (1.0 ml) was added NaOMe (25.8 mg, 0.478 mmol) at 0 C, and the mixture was stirred for 4 h at rt under an argon atmosphere.…”
Section: Methodsmentioning
confidence: 99%
“…1 -4 These methods are based on the interpretation of 1 H NMR shift changes of esterified 1 -3 or glucosylated 4 alcohols that are induced by anisotropic effects.…”
Section: Introductionmentioning
confidence: 99%
“…The structural elucidation of natural products has always been a problem that puzzles chemists, although new methods are constantly being developed. At present, a tricky problem is the assignment of the relative configuration in such conformational flexible 1-oxygenated 1,2-diarylpropan-3-ols containing two adjacent stereogenic centers. There are several common methods enabling a relative configuration elucidation, including applying derivatization with chiral reagents, using J -based configuration analysis, examining the intensity of the nuclear Overhauser effect, and relying on quantum-chemical calculations or X-ray crystallographic analysis. Among these, the NMR technique is a convenient and useful procedure for the determination of a relative configuration of organic molecules.…”
mentioning
confidence: 99%