Joining Hydroxyazobenzene and Mannose under Mitsunobu Conditions

• Published in: Israel journal of chemistry Vol. 55; no. 3-4; pp. 383 - 386
• Main Authors: Hain, Julia, Chandrasekaran, Vijayanand, Lindhorst, Thisbe K.
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 01.04.2015; WILEY‐VCH Verlag; Wiley Subscription Services, Inc
• Subjects: Adhesion; azobenzene glycosides; Bacteria; carbohydrates; Derivatives; glycoconjugates; Glycosides; Mannose; Mitsunobu reaction; photoswitchable glycoconjugates; Sweets; Switches; Switching
• ISSN: 0021-2148; 1869-5868
• DOI: 10.1002/ijch.201400211

The Mitsunobu reaction has been revisited to join hydroxyazobenzene and mannose derivatives to supply photoswitchable glycoconjugates. These are suited to modulating and controlling carbohydrate‐lectin interactions, as well as to switching bacterial adhesion to surfaces. Employing hydroxyazobenzene in a Mitsunobu protocol, free mannose led to a mixture of azobenzene pyranosides and furanosides. Protected reducing mannose derivatives can give good yields of azobenzene β‐D‐mannopyranoside, and unprotected alkyl α‐D‐mannosides can be converted to 6‐O‐azobenzene‐modified glycosides in a single step. Thus, valuable “sweet switches” can be obtained under Mitsunobu conditions, requiring a minimum (or no) protecting group chemistry.