132842-19-4Relevant articles and documents
Total Synthesis of (2S,3S,4R)-2--16-methylheptadecane-1,3,4-triol 3,4-dibenzoate, a Partially Protected Ceramide Part of Sponge Cerebrosides
Nakashima, Hideki,Hirata, Norihiko,Iwamura, Takeru,Yamagiwa, Yoshiro,Kamikawa, Tadao
, p. 2849 - 2858 (2007/10/02)
(2S,3S,4R)-2--16-methylheptadecane-1,3,4-triol 3,4-dibenzoate 32, apertially protected ceramide part of a cerebroside from the marine sponge Halichondria japonica, has been synthesized from L-ascorbic acid, and its absolute stereochemistry has been determined.The key steps in the synthesis include the regioselective ring opening of chiral epoxide 5 with a 2-alkyl-2-lithio-1,3-dithiane and the introduction of a hydroxymethylene synthon using Dondoni's protocol to assemble C(1) and C(2) functionality.