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Synthesis of α‐Arabinose Nucleosides from 6‐Substituted Uracils
Author(s) -
Jørgensen Per T.,
ElBarbary Ahmed A.,
Pedersen Erik B.
Publication year - 1993
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.199319930102
Subject(s) - chemistry , arabinose , uracil , combinatorial chemistry , stereochemistry , organic chemistry , biochemistry , xylose , dna , fermentation
The reaction of silylated 6‐substituted uracils 5 with methyl 2,3,5‐tri‐ O ‐benzoyl‐α‐ D ‐arabinofuranoside ( 3 ) in the presence of trimethylsilyl trifluoromethanesulfonate (TMS triflate) afforded a mixture of the corresponding protected N 1 , N 3 ‐bis(arabinofuranosyl)uracils 6 and the 6‐substituted 2,3,5‐tri‐ O ‐benzoyl‐α‐ D ‐arabinofuranosyluracils 8 . Deprotection of 6 and 8 gave the corresponding α nucleosides 7 and 9 . The reaction of silylated 6‐ethyl‐ and 6‐methylthiouracil with 3 afforded a mixture of S‐ and N 3 ‐glycosides 10 and 11 . The glycosides 10 were deblocked by treatment with methanolic ammonia to obtain the deprotected α nucleosides 12 .