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Synthesis of optically active seven-membered 1,5-anhydrocarbasugars and 1,4,5-tribenzoyloxy-2-ethoxy cycloheptanes via [5+2] cycloaddition

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Title Synthesis of optically active seven-membered 1,5-anhydrocarbasugars and 1,4,5-tribenzoyloxy-2-ethoxy cycloheptanes via [5+2] cycloaddition
 
Creator YADAV, AA
SARANG, PS
SAU, M
THIRUMALAIRAJAN, S
TRIVEDI, GK
SALUNKHE, MM
 
Subject Carbasugar
Cyclitol
3-Oxidopyrylium ylide
Cycloaddition
Stereocontrol
CATALYZED ASYMMETRIC DIHYDROXYLATION
RING-CLOSING METATHESIS
STEREOSELECTIVE-SYNTHESIS
ENANTIOMERICALLY PURE
ANALOGS
3-OXIDOPYRYLIUM
POLYCYCLITOLS
CONDURITOLS
DERIVATIVES
GLYCOSIDASES
 
Description [5+2] Cycloaddition followed by asymmetric dihydroxylation procedure have been utilized to prepare novel cyclitols. Accordingly, rac-2 alpha-hydroxy-6 alpha-ethoxy-1,5-anhydro cyclohept-3-ene, 10 derived from [5+2] cycloaddition of 3-oxidopyrylium ylide and vinyl ether has been recognized as a seven-membered carbasugar equivalent and elaborated to 1,4,5-tribenzoyloxy-2-ethoxy cycloheptanes through a flexible, regio- and stereoselective strategy involving Sharpless asymmetric dihydroxylation conditions to resolve the compounds obtained. The structures and relative configurations of newly synthesized (+)-2 alpha-acetoxy-6 alpha-ethoxy-3 beta,4 beta-dihydroxy-1,5-anhydro cycloheptane ((+)-12)); (-)-1 beta,4 beta,5 beta-tribenzoyloxy-6 alpha-ethoxy cycloheptane ((-)-17) and (+)-1 alpha,4 alpha,5 alpha-tribenzoyloxy-6 beta-ethoxy cycloheptane ((+)-17) are unambiguously established by single crystal X-ray analysis and duly supported by H-1 and C-13 NMR spectroscopy data. (C) 2012 Elsevier Ltd. All rights reserved.
 
Publisher PERGAMON-ELSEVIER SCIENCE LTD
 
Date 2014-10-14T12:41:26Z
2014-10-14T12:41:26Z
2012
 
Type Article
 
Identifier TETRAHEDRON LETTERS, 53(28)3599-3602
http://dx.doi.org/10.1016/j.tetlet.2012.05.014
http://dspace.library.iitb.ac.in/jspui/handle/100/14431
 
Language en