Stereospecific Synthesis of (-)-allo-Muscarine from D-Glucose: Novel Routes to the Key Chiral Synthon

[img]PDF - Authorized users only
Language: English
47Kb
Title:Stereospecific Synthesis of (-)-allo-Muscarine from D-Glucose: Novel Routes to the Key Chiral Synthon
Creators:
Popsavin, Velimir
Beric, Ostoja
Popsavin, Mirjana
Csanádi, János
Lajšic, Stevan
Miljković, Dušan
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 62, 5, pp. 809-815
Uncontrolled Keywords:2,5-Anhydro sugars, (-)-<i>allo</i>-Muscarine, 3,6-Thioanhydro sugars, D-Glucose

Abstract

The key chiral synthon in a novel synthesis of (-)-<i>allo</i>-muscarine from D-glucose has been prepared by three independent routes. The most efficient one includes a four-step conversion <i>via</i> the 4-<i>O</i>-benzoyl derivatives of starting 2,5-anhydro-3,5-di-<i>O</i>-methanesulfonyl-L-idose ethylene acetal (<strong>2a</strong>) into 2,5-anhydro-3,6-dideoxy-L-<i>lyxo-</i>hexose ethylene acetal (<strong>4b</strong>). The intermediate <strong>4b</strong> was efficiently converted into the chiral synthon 2,5-anhydro-4-<i>O</i>-benzoyl-3,6-dideoxy-L-<i>arabino</i>-hexose (<strong>4c</strong>) by Mitsunobu reaction.

Title:Stereospecific Synthesis of (-)-allo-Muscarine from D-Glucose: Novel Routes to the Key Chiral Synthon
Creators:
Popsavin, Velimir
Beric, Ostoja
Popsavin, Mirjana
Csanádi, János
Lajšic, Stevan
Miljković, Dušan
Uncontrolled Keywords:2,5-Anhydro sugars, (-)-<i>allo</i>-Muscarine, 3,6-Thioanhydro sugars, D-Glucose
Divisions:Life and Chemical Sciences > Institute of Organic Chemistry and Biochemistry > Collection of Czechoslovak Chemical Communications
Journal or Publication Title:Collection of Czechoslovak Chemical Communications
Volume:62
Number:5
Page Range:pp. 809-815
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc19970809UNSPECIFIED
ID Code:1162
Item Type:Article
Deposited On:06 Feb 2009 17:07
Last Modified:06 Feb 2009 16:07

Citation

Popsavin, Velimir; Beric, Ostoja; Popsavin, Mirjana; Csanádi, János; Lajšic, Stevan; Miljković, Dušan (1997) Stereospecific Synthesis of (-)-allo-Muscarine from D-Glucose: Novel Routes to the Key Chiral Synthon. Collection of Czechoslovak Chemical Communications, 62 (5). pp. 809-815. ISSN 0010-0765

Repository Staff Only: item control page