Straighforward Synthesis of a Novel Chiron and its Application to the Synthesis of (+)‐1,4‐Dideoxymannojirimycin and Further Polyoxygenated 2‐Pyperidones | Zendy

Ramírez Elsie | Zendy; MezaLeón Rosa L. | Zendy; Quintero Leticia | Zendy; Höpfl Herbert | Zendy; CruzGregorio Silvano | Zendy; SartilloPiscil Fernando | Zendy

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Straighforward Synthesis of a Novel Chiron and its Application to the Synthesis of (+)‐1,4‐Dideoxymannojirimycin and Further Polyoxygenated 2‐Pyperidones

Author(s) -

Ramírez Elsie,

MezaLeón Rosa L.,

Quintero Leticia,

Höpfl Herbert,

CruzGregorio Silvano,

SartilloPiscil Fernando

Publication year - 2017

Publication title -

chemistryselect

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.437

H-Index - 34

ISSN - 2365-6549

DOI - 10.1002/slct.201602048

Subject(s) - chemistry , moiety , enantiopure drug , stereoselectivity , hydrolysis , stereochemistry , wittig reaction , bond cleavage , amine gas treating , oxidative cleavage , derivative (finance) , total synthesis , organic chemistry , catalysis , enantioselective synthesis , financial economics , economics

The total synthesis of (+)‐1,4‐dideoxymannojimycin and the enantiopure synthesis of three polyoxygenated piperidin‐2‐ones from a novel chiron is reported. Starting from 3‐deoxy‐3‐amine‐D‐glucose, by means of the stereoselective aqueous SHOWO protocol (Sequential‐Hydrolysis‐Oxidation‐Wittig Olefination), the unsaturated‐7,3‐lactam‐D‐xylofuranose derivative was prepared, which depending on the oxidative C−C bond cleavage reaction conditions for the furanose moiety, is transformed into either (+)‐1,4‐dideoxymannojirimycin or polyoxygenated piperidin‐2‐ones.

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