title: A neighboring group participation strategy: direct and highly diastereoselective synthesis of 2-substituted and 2,2-bisubstituted perhydrofuro[2,3-b]pyran derivatives.
abstract: Treatment of methyl 2-C-formylmethyl-2-deoxy-β-D-glucopyranoside (5) or methyl 2-C-acetylmethyl-2-deoxy-β-D-glucopyranoside (1) with H2SO4–HOAc–Ac2O gave 2-acetoxyl-4,5-bis(benzyloxy)-6-[(benzyloxy)methyl]hexahydrofuro[2,3-b]pyran (6) and acetyl 2-C-acetylmethyl-2-deoxy-α-D-glucopyranoside (7) respectively, which were further reacted with nucleophiles in the presence of TMSOTf and offered a series of 2-substituted and 2,2-disubstituted perhydrofuro[2,3-b]pyran derivatives in high yield with excellent diastereoselectivity.
authors.affiliation: Natural Products Research Center, Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu 610041, China. shaohw@cib.ac.cn.
authors.forename: Xiaofeng
authors.initials: X
authors.lastname: Ma
authors.forename: Qin
authors.initials: Q
authors.lastname: Tang
authors.forename: Jun
authors.initials: J
authors.lastname: Ke
authors.forename: Jichao
authors.initials: J
authors.lastname: Zhang
authors.forename: Xinglong
authors.initials: X
authors.lastname: Yang
authors.forename: Xudong
authors.initials: X
authors.lastname: Shen
authors.forename: Huawu
authors.initials: H
authors.lastname: Shao
mesh_terms: D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis* / Q000737:chemistry; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D011714:Pyrans / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D019086:Bridged Bicyclo Compounds, Heterocyclic; D005663:Furans; D011714:Pyrans