A comparison of benzyl and 2-naphthylmethyl ethers as permanent hydroxyl protecting groups in the synthesis of α-galactoglycosphingolipids KRN7000 and PBS-57. Issue 4 (13th June 2017)

• Record Type: Journal Article
• Authors: Yao, Dongming; Liu, Yichu; Gao, Qi; Sui, Qiang; Liu, Xiaoping; Ding, Ning
• Is Part Of: Journal of carbohydrate chemistry. Volume 36:Issue 4/6(2017)
• Page Start: 173
• Page End: 188
• Publication Date: 2017-06-13
• Subjects: α-GalGSLs -- KRN7000 -- 2-naphthylmethyl -- catalytic hydrogenolysis -- PBS-57; Carbohydrates -- Periodicals; 547.78
• DOI: 10.1080/07328303.2017.1375114
• Languages: English
• ISSNs: 0732-8303

Abstract

GRAPHICAL ABSTRACT: ABSTRACT: Due to the interest in the biological properties of marine derived α-galactoglycosphingolipids (α-GalGSLs), a lot of work has focused on the development of their synthesis. Here we conducted the direct comparison of benzyl and 2-naphthylmethyl (Nap) ethers as permanent hydroxyl protecting groups for the synthesis of KRN7000, as well as the practical synthesis of a biologically active α-GalGSLs PBS-57. This work further revealed the advantages of Nap ether over benzyl ether for permanent hydroxyl protection in the synthesis of α-GalGSLs.