Synthesis of L-enantiomers of 4'-thioarabinofuranosyl pyrimidine nucleosides.
L-Enantiomers of 4'-thioarabinofuranosyl pyrimidine nucleosides were synthesized from D-xylose. Methyl 2,3,5-tri-O-benzyl-D-xylofuranoside 6 was converted to the corresponding xylitol 7, which was treated with MsCl and then Na2S to give 1,4-anhydro-L-4-thioarabitol 8. As previously reported, Pummerer rearrangement of 8 followed by glycosylation with a silylated thymine and N4-acetylcytosine derivative and deprotection gave the corresponding alpha- and beta-L-4'-thioarabinofuranosyl pyrimidine nucleosides.
Satoh
H
H
Biochemicals Division, Yamasa Corporation, Chiba, Japan.
Yoshimura
Y
Y
Sakata
S
S
Miura
S
S
Machida
H
H
Matsuda
A
A
D000964:Antimetabolites, Antineoplastic / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D001087:Arabinonucleosides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D002470:Cell Survival / Q000187:drug effects; D006031:Glycosylation; D018259:Herpesvirus 1, Human / Q000187:drug effects; D018258:Herpesvirus 2, Human / Q000187:drug effects; D006801:Humans; D007202:Indicators and Reagents; D015458:Leukemia, T-Cell; D008968:Molecular Conformation; D009904:Optical Rotation; D011741:Pyrimidine Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D014407:Tumor Cells, Cultured; D014994:Xylose
D000964:Antimetabolites, Antineoplastic; D000998:Antiviral Agents; D001087:Arabinonucleosides; D007202:Indicators and Reagents; D011741:Pyrimidine Nucleosides; D014994:Xylose