Open AccessFrom d - to l -Monosaccharide Derivatives via Photodecarboxylation–Alkylation
Author(s) -
Ieng Chim Wan,
Martin D. Witte,
Adriaan J. Minnaard
Publication year - 2019
Publication title -
organic letters
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.94
H-Index - 239
eISSN - 1523-7060
pISSN - 1523-7052
DOI - 10.1021/acs.orglett.9b03016
Subject(s) - chemistry , monosaccharide , alkylation , yield (engineering) , stereochemistry , organic chemistry , catalysis , materials science , metallurgy
Photodecarboxylation-alkylation of conformationally locked monosaccharides leads to inversion of stereochemistry at C5. This allows the synthesis of l-sugars from their readily available d-counterparts. Via this strategy, methyl l-guloside was synthesized from methyl d-mannoside in 21% yield over six steps.
Accelerating Research
Robert Robinson Avenue,
Oxford Science Park, Oxford
OX4 4GP, United Kingdom
Address
John Eccles HouseRobert Robinson Avenue,
Oxford Science Park, Oxford
OX4 4GP, United Kingdom