17673-74-4Relevant articles and documents
Total synthesis of sulfated glycosphingolipid SM1a, a kind of human epithelial carcinoma antigen
Zhang, Pengtao,Wang, Kun,Zhang, Jun,Li, Chunxia,Guan, Huashi
, p. 570 - 583 (2015/01/30)
A highly efficient and practical total synthesis of the sulfated ganglioside SM1a, a kind of human epithelial carcinoma antigen identified in mammalian kidney, has been accomplished for the first time. The characteristic sequence of SM1a, β-D-Galp-(1→3)-β
A NOVEL ROUTE TO D-erythro-SPHINGOSINE AND RELATED COMPOUNDS FROM MONO-O-ISOPROPYLIDENE-D-XYLOSE OR -D-GALACTOSE
Kiso, Makoto,Nakamura, Akemi,Tomita, Yoshimi,Hasegawa, Akira
, p. 101 - 112 (2007/10/02)
An efficient synthesis of D-erythro-sphingosine and -ceramide from D-xylose or D-galactose is described.A mixture of 2,4-O-isopropylidene-D-threose and its formate, which is available in one step from 3,5-O-isopropylidene-D-xylofuranose or 4,6-O-isopropylidene-D-galactopyranose, was subjected to the Wittig alkenation with triphenylphosphonio-tetra- and -hexa-decylid.The resulting 1,3-O-isopropylidenated C18 and C20 alkenes were each transformed, by introduction of an azido group at C-2, and selective reduction of the azide, into the corresponding 1,3-O-protected sphingosines that have the 2(S),3(R)-D-erythro configuration, from which a variety of ceramides were prepared by the sequence of N-acylation with the stearoyl or lignoceroyl group, and hydrolytic removal of the isopropylidene group.Some ceramides were also obtained by direct N-acylations of the corresponding sphingosines.