Chiral Brønsted Acid Mediated Glycosylation with Recognition of Alcohol Chirality | Zendy

Kimura Tomoya | Zendy; Sekine Maiko | Zendy; Takahashi Daisuke | Zendy; Toshima Kazunobu | Zendy

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Chiral Brønsted Acid Mediated Glycosylation with Recognition of Alcohol Chirality

Author(s) -

Kimura Tomoya,

Sekine Maiko,

Takahashi Daisuke,

Toshima Kazunobu

Publication year - 2013

Publication title -

angewandte chemie international edition

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 5.831

H-Index - 550

eISSN - 1521-3773

pISSN - 1433-7851

DOI - 10.1002/anie.201304830

Subject(s) - chemistry , glycosylation , chirality (physics) , glycoside , enantiomer , alcohol , phosphoric acid , yield (engineering) , sugar , stereochemistry , organic chemistry , biochemistry , chiral symmetry , materials science , physics , quantum mechanics , nambu–jona lasinio model , quark , metallurgy

Sugar sugar : In the glycosylation of racemic alcohols with 1 using the chiral phosphoric acid 2 as an activator, one enantiomer of the racemic alcohol selectively reacts with 1 to give the corresponding glycoside with good to excellent α/β‐stereo‐ and diastereoselectivity in high yield. The reaction was successfully applied to the synthesis of a chiral natural flavan glycoside using a racemic aglycon.

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