Stereodivergent De Novo Synthesis of Branched Amino Sugars by Lewis Acid Promoted Rearrangement of 1,2‐Oxazines | Zendy

Pfrengle Fabian | Zendy; Lentz Dieter | Zendy; Reißig HansUlrich | Zendy

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Stereodivergent De Novo Synthesis of Branched Amino Sugars by Lewis Acid Promoted Rearrangement of 1,2‐Oxazines

Author(s) -

Pfrengle Fabian,

Lentz Dieter,

Reißig HansUlrich

Publication year - 2009

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.200805724

Subject(s) - oxazines , chemistry , sugar , lewis acids and bases , bicyclic molecule , amino acid , stereochemistry , organic chemistry , catalysis , biochemistry

Well concealed : 1,2‐oxazines such as 1 rearrange under Lewis acidic conditions to bicyclic products of type 2 , which can be incorporated into oligosaccharides as protected amino sugar equivalents. Subsequent reductive steps provide unusual oligosaccharides 3 having C2‐branched 4‐amino sugar units. Most of the reactions proceed with excellent stereocontrol and allow the synthesis of a collection of stereoisomers.

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