A flexible approach to construct three contiguous chiral centers of sphingolipids, and asymmetric synthesis of D-ribo-phytosphingosine and its derivatives

作者：Xarnod Cholmen; Huang Wei; Ren Rong Guo; Liu Ru Cheng; Wei Bang Guo^*

来源：Tetrahedron, 2012, 68(33): 6688-6695.

DOI：10.1016/j.tet.2012.05.120

• alpha-Galactosylceramide
• Ceramide
• Sphingolipid
• Asymmetric synthesis
• Phytosphingosine

An efficient approach to build the three contiguous stereogenic centers of sphingosine unit starting from cheap glutamic acid is described. The key step of this approach is the SmI2-mediated cross-coupling of chiral N-tert-butanesulfinyl imine 11 with sterically hindered aliphatic aldehyde 9 or 21 to construct hydroxymethyl beta-amino alcohol 10 or 22 in high diastereoselectivity (>99%, de). The utility of this flexible method has been demonstrated in the synthesis of D-ribo-phytosphingosine 1, its two derivatives 18 and 29. Moreover, a practicable synthetic route for synthesis of various sphingolipids, ceramides, alpha-galactosylceramides and their derivatives is also described.

• 出版日期2012-8-19
• 单位复旦大学