title: Rapid access to 6″-functionalized α-galactosyl ceramides by using 2-naphthylmethyl ether as the permanent protecting group.
abstract: A versatile strategy for the synthesis of 6″-functionalized α-GalCers by using NAP ether group for permanent hydroxyl protection was developed, which provide the flexibility necessary for the incorporation of a wide range of functional groups in target molecules including alkyne, azide, thiol that are intolerant to Pd-catalyzed hydrogenolysis as well as other functionalities like carboxylic acid and amine. This strategy is also adaptable to other glycoconjugate synthesis especially those containing clickable tags and unsaturated functionalities.
authors.affiliation: Department of Medicinal Chemistry, School of Pharmacy, Fudan University, Shanghai 201203, China.
authors.forename: Yichu
authors.initials: Y
authors.lastname: Liu
authors.affiliation: China State Institute of Pharmaceutical Industry, Shanghai 201203, China.
authors.forename: Xiaoyan
authors.initials: X
authors.lastname: Xu
authors.affiliation: China State Institute of Pharmaceutical Industry, Shanghai 201203, China.
authors.forename: Qi
authors.initials: Q
authors.lastname: Gao
authors.affiliation: Department of Medicinal Chemistry, School of Pharmacy, Fudan University, Shanghai 201203, China.
authors.forename: Shiqiang
authors.initials: S
authors.lastname: Yan
authors.affiliation: Department of Medicinal Chemistry, School of Pharmacy, Fudan University, Shanghai 201203, China.
authors.forename: Yingxia
authors.initials: Y
authors.lastname: Li
authors.affiliation: Department of Medicinal Chemistry, School of Pharmacy, Fudan University, Shanghai 201203, China. Electronic address: dingning@fudan.edu.cn.
authors.forename: Ning
authors.initials: N
authors.lastname: Ding
mesh_terms: D000276:Adjuvants, Immunologic / Q000138:chemical synthesis* / Q000737:chemistry; D000480:Alkynes / Q000138:chemical synthesis / Q000737:chemistry; D001386:Azides / Q000138:chemical synthesis / Q000737:chemistry; D002384:Catalysis; D057930:Click Chemistry; D004987:Ethers / Q000737:chemistry; D005699:Galactosylceramides / Q000138:chemical synthesis* / Q000737:chemistry; D008745:Methylation; D010165:Palladium / Q000737:chemistry; D013438:Sulfhydryl Compounds / Q000138:chemical synthesis / Q000737:chemistry
chemical_list: D000276:Adjuvants, Immunologic; D000480:Alkynes; D001386:Azides; D004987:Ethers; D005699:Galactosylceramides; D013438:Sulfhydryl Compounds; C493154:alpha-galactosylceramide; D010165:Palladium; C103873:KRN 7000
keywords: Clickable tag; Glycolipid; Naphthylmethyl ether; Self-adjuvanting vaccine; α-GalCers