A facile and practical synthesis of peracylated 4-thio-D-ribofuranoses from D-glucose.
A practical synthesis of a peracylated 4-thio-D-ribofuranose 14 starting from inexpensive d-glucose is described. The C2-C6 portion of D-glucose was utilized, in which sulfur was introduced to C5 in two consecutive displacement reactions with net retention of configuration under mild conditions.
Sun
Zhi-Hua
ZH
Department of Chemistry, Fudan University, 220 Handan Road, Shanghai 200433, China wangbing@fudan.edu.cn.
Wang
Bing
B
D000085:Acetates / Q000138:chemical synthesis; D000215:Acylation; D001565:Benzoates / Q000138:chemical synthesis; D005663:Furans / Q000138:chemical synthesis*; D005947:Glucose / Q000737:chemistry*; D012266:Ribose / Q000031:analogs & derivatives* / Q000737:chemistry
D000085:Acetates; D001565:Benzoates; D005663:Furans; D012266:Ribose; D005947:Glucose