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Stereoselective synthesis of beta-amino alcohols: practical preparation of all four stereomers of N-PMB-protected sphingosine from L- and D-serine SCIE SCOPUS
- Title
- Stereoselective synthesis of beta-amino alcohols: practical preparation of all four stereomers of N-PMB-protected sphingosine from L- and D-serine
- Date Issued
- 1999-04-23
- Publisher
- PERGAMON-ELSEVIER SCIENCE LTD
- Abstract
- Serine was efficiently converted to the N-p-methoxybenzyl (PMB) protected alpha'-amino enone derivative 6, which was reduced with Zn(BH4)(2) to the corresponding anti-beta-amino alcohol in >96% de. On the other hand, N-PMB-N-Boc-protected alpha'-amino enone derivative 8 was reduced by NaBH4 to syn-product with a diastereoselectivity of ca. 90%. (C) 1999 Elsevier Science Ltd. All rights reserved.
- Keywords
- D-ERYTHRO-SPHINGOSINE; D-THREO-SPHINGOSINE; ASYMMETRIC SYNTHESES; ORGANIC-SYNTHESIS; EMMONS REACTION; CELL-ADHESION; ACIDS; ALPHA; REDUCTION; ALDEHYDES
- ISSN
- 0957-4166
- Article Type
- Article
- Citation
- TETRAHEDRON-ASYMMETRY, vol. 10, no. 8, page. 1441 - 1444, 1999-04-23
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