TY - JOUR
T1 - A facile method for preparation of 3-thio-sugars and 3-thio-glycals. synthesis of 3′-mercapto-3′-deamino-doxorubicin
AU - Priebe, Waldemar
AU - Grynkiewicz, Grzegorz
AU - Neamati, Nouri
AU - Perez-Soler, Roman
N1 - Copyright:
Copyright 2014 Elsevier B.V., All rights reserved.
PY - 1991/7/8
Y1 - 1991/7/8
N2 - General method for the preparation of synthetically useful 3-thio-glycals and biologically important 3-thio-sugars is described. The 3-thio-2,3,6-trideoxy-L-hexopyranoses (13, 14) and corresponding 3-S-acetyl-1,5-anhydro-3-thio-L-hex-1-enitols (15-18) were synthesized using 3,4-di-O-acetyl-L-fucal (1) and 3,4-di-O-acetyl-L-rhamnal (2) as substrates. The 3-thio-glycals were successfully employed for the synthesis of 3′-mercapto-3′-deamino-doxorubicin and its analogues.
AB - General method for the preparation of synthetically useful 3-thio-glycals and biologically important 3-thio-sugars is described. The 3-thio-2,3,6-trideoxy-L-hexopyranoses (13, 14) and corresponding 3-S-acetyl-1,5-anhydro-3-thio-L-hex-1-enitols (15-18) were synthesized using 3,4-di-O-acetyl-L-fucal (1) and 3,4-di-O-acetyl-L-rhamnal (2) as substrates. The 3-thio-glycals were successfully employed for the synthesis of 3′-mercapto-3′-deamino-doxorubicin and its analogues.
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U2 - 10.1016/S0040-4039(00)92694-7
DO - 10.1016/S0040-4039(00)92694-7
M3 - Article
AN - SCOPUS:0025829055
SN - 0040-4039
VL - 32
SP - 3313
EP - 3316
JO - Tetrahedron Letters
JF - Tetrahedron Letters
IS - 28
ER -