In:
Helvetica Chimica Acta, Wiley, Vol. 64, No. 3 ( 1981-04-29), p. 775-786
Abstract:
Stereoselective Hydride Reduction of Tetronic Acid Derivatives, Synthesis of Branched‐Chain Tetrofuranoses The 3‐methoxymethyl derivatives of 2‐methyl‐ D , L ‐threofuranose ( 10a ) and 2‐deoxy‐2‐methyl‐ D , L ‐erythrofuranose ( 11a ) are prepared starting from 2‐methyl‐tetronic acid ( 1 ). The key step is the stereoselective reduction of the 3‐oxo‐function of 2‐chloro‐2‐methyl‐3‐oxo‐γ‐butyrolacton ( 2 ) by sodiumborohydride, which proceeds predominantly anti with respect to the C,Cl‐bond. The configuration of the reduction products has been established by 1 H‐ and 13 C‐NMR.‐spectroscopy.
Type of Medium:
Online Resource
ISSN:
0018-019X
,
1522-2675
DOI:
10.1002/hlca.19810640317
Language:
English
Publisher:
Wiley
Publication Date:
1981
detail.hit.zdb_id:
74-7
detail.hit.zdb_id:
1475013-2