A facile method for preparation of 3-thio-sugars and 3-thio-glycals. synthesis of 3′-mercapto-3′-deamino-doxorubicin

Waldemar Priebe, Grzegorz Grynkiewicz, Nouri Neamati, Roman Perez-Soler

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

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.

Original languageEnglish (US)
Pages (from-to)3313-3316
Number of pages4
JournalTetrahedron Letters
Volume32
Issue number28
DOIs
StatePublished - Jul 8 1991
Externally publishedYes

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Thiosugars
Doxorubicin
Substrates

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

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A facile method for preparation of 3-thio-sugars and 3-thio-glycals. synthesis of 3′-mercapto-3′-deamino-doxorubicin. / Priebe, Waldemar; Grynkiewicz, Grzegorz; Neamati, Nouri; Perez-Soler, Roman.

In: Tetrahedron Letters, Vol. 32, No. 28, 08.07.1991, p. 3313-3316.

Research output: Contribution to journalArticle

Priebe, Waldemar ; Grynkiewicz, Grzegorz ; Neamati, Nouri ; Perez-Soler, Roman. / A facile method for preparation of 3-thio-sugars and 3-thio-glycals. synthesis of 3′-mercapto-3′-deamino-doxorubicin. In: Tetrahedron Letters. 1991 ; Vol. 32, No. 28. pp. 3313-3316.
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