Photochemical Synthesis of an  L ‐Erythrose Building Block and Its use in the Preparation of Methyl 2,3, O ‐Isopropylidene‐β‐ L ‐apio‐ L ‐furanoside | Zendy

Nehrings Alfred | Zendy; Scharf HansDieter | Zendy; Runsink Jan | Zendy

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Photochemical Synthesis of an L ‐Erythrose Building Block and Its use in the Preparation of Methyl 2,3, O ‐Isopropylidene‐β‐ L ‐apio‐ L ‐furanoside

Author(s) -

Nehrings Alfred,

Scharf HansDieter,

Runsink Jan

Publication year - 1985

Publication title -

angewandte chemie international edition in english

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 5.831

H-Index - 550

eISSN - 1521-3773

pISSN - 0570-0833

DOI - 10.1002/anie.198508771

Subject(s) - cycloaddition , block (permutation group theory) , chemistry , stereochemistry , combinatorial chemistry , medicinal chemistry , catalysis , organic chemistry , combinatorics , mathematics

The synthesis of branched carbohydrates , e.g., the title compound 2 , from nonsugar building blocks is achieved by a chirally controlled photoaldol reaction. [2+2] Cycloaddition of (−)‐8‐phenylmenthyl phenylglyoxylate PhCOCO 2 R * to 2,2‐dimethyl‐1,3‐dioxole leads in exo fashion diastereoselectively to 1 , one of four possible oxetanes; 1 is then converted in several steps into 2 .

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