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

Trujillo, Mar; Morales, Ezequiel Q.; Vázquez, Jesús T.

doi:10.1021/jo00101a023

Cited by 37 publications

(19 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…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%

Synthesis and Bioactivity of Potassium β-D-Glucopyranosyl 12-Hydroxy Jasmonate and Related Compounds

Nakamura

Miyatake

Inomata

2008

Bioscience, Biotechnology, and Biochemistry

View full text Add to dashboard Cite

Albizzia saman, a leguminous plant, is known to open its leaves in the daytime and sleep at night with the leaves folded. -D-Glucopyranosyl 12-hydroxyjasmonate (1) was isolated as an endogenous chemical factor controlling this leafmovement. We developed a concise synthesis of optically pure (À)-1 in 9 steps from (+)-2 with a total yield of 58%. Similarly, such analogs of 1 as epi-LCF (13), enantiomer (14), and galactoside (19) were synthesized for a structure activity relationship (SAR) study. The results of this SAR study strongly suggest that the mechanism for the leaf-closing activity of 1 would be different from that of methyl jasmonate, and also suggest the involvement of a different kind of target protein which recognizes the trans-isomer of a jasmonate derivative.

show abstract

Section: Methodsmentioning

confidence: 99%

Synthesis and Bioactivity of Potassium β-D-Glucopyranosyl 12-Hydroxy Jasmonate and Related Compounds

Nakamura

Miyatake

Inomata

2008

Bioscience, Biotechnology, and Biochemistry

View full text Add to dashboard Cite

show abstract

“…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%

Monosaccharides as internal probes for the determination of the absolute configuration of 2-butanol

et al. 2006

View full text Add to dashboard Cite

D-Glucose, D-mannose and L-rhamnose were reacted with a racemic mixture of 2-butanol, and the resulting alpha-glycosides were analyzed by 1H NMR with COSY and NOESY experiments. Conformational analysis of alpha-glycosidic bonds performed with molecular modeling and appropriate heteronuclear long-range coupling measurements and combined with analysis of dipolar couplings observed in NOESY spectra allowed the assignment of absolute configuration in the aglycones of elucidated alpha-glycosides.

show abstract

“…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%

Rapid Approaches for Assignment of the Relative Configuration in 1-Oxygenated 1,2-Diarylpropan-3-ols by ¹H NMR Spectroscopy

et al. 2021

View full text Add to dashboard Cite

The structural elucidation of chiral molecules with more than one stereocenter is usually a tricky problem. In this paper, efficient 1H NMR spectroscopic approaches for assigning the erythro and threo configurations of 1-oxygenated 1,2-diarylpropan-3-ols were developed. By analysis of the chemical shift differences of diastereotopic methylene H2-3 (Δδ3) in CDCl3 or the chemical shift differences of H-1 and H-2 (Δδ1,2) in methanol-d 4, deuterated dimethyl sulfoxide, and acetone-d 6, the configurations of 1-oxygenated 1,2-diarylpropan-3-ols can be rapidly and conveniently determined.

show abstract

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

Cited by 37 publications

References 0 publications

Synthesis and Bioactivity of Potassium β-D-Glucopyranosyl 12-Hydroxy Jasmonate and Related Compounds

Synthesis and Bioactivity of Potassium β-D-Glucopyranosyl 12-Hydroxy Jasmonate and Related Compounds

Monosaccharides as internal probes for the determination of the absolute configuration of 2-butanol

Rapid Approaches for Assignment of the Relative Configuration in 1-Oxygenated 1,2-Diarylpropan-3-ols by ¹H NMR Spectroscopy

Contact Info

Product

Resources

About

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

Cited by 37 publications

References 0 publications

Synthesis and Bioactivity of Potassium β-D-Glucopyranosyl 12-Hydroxy Jasmonate and Related Compounds

Synthesis and Bioactivity of Potassium β-D-Glucopyranosyl 12-Hydroxy Jasmonate and Related Compounds

Monosaccharides as internal probes for the determination of the absolute configuration of 2-butanol

Rapid Approaches for Assignment of the Relative Configuration in 1-Oxygenated 1,2-Diarylpropan-3-ols by 1H NMR Spectroscopy

Contact Info

Product

Resources

About

Rapid Approaches for Assignment of the Relative Configuration in 1-Oxygenated 1,2-Diarylpropan-3-ols by ¹H NMR Spectroscopy