Serine as chiral educt for the practical synthesis of enantiopure N-protected beta-hydroxyvaline.
Serine as chiral educt for the practical synthesis of enantiopure N-protected beta-hydroxyvaline.
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丝氨酸作为手性离析物，用于对映体纯 N-保护的 β-羟基缬氨酸的实际合成。
DOI：
10.1021/jo026260b
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发表时间：
2003
期刊：
影响因子：
--
通讯作者：
W. Lubell
中科院分区：
文献类型：
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作者：
J. E. Dettwiler;W. Lubell
以N-保护的丝氨酸甲酯2a和2b为原料，经两步反应合成了对映体纯的N-叔丁氧羰基-和N-苯磺酰基-β-羟基缬氨酸1a和1b。将CH（3）MgBr加入到2a和2b中，分别以83%和81%的产率得到作为主要产物的二醇3a和3b。使用克里思、NaClO（2）、NaOCl混合物进行二醇3a和3b的选择性氧化，产率分别为96%和93%。该两步法有效地提供了数克量的对映体纯N-Boc-β-羟基缬氨酸1a。
N-tert-Butyloxycarbonyl- and N-benzenesulfonyl-beta-hydroxyvalines 1a and 1b were, respectively, synthesized in enantiomerically pure form by a two-step protocol from their enantiomeric N-protected serine methyl esters 2a and 2b. The addition of CH(3)MgBr to 2a and 2b provided diols 3a and 3b, respectively as major products in 83% and 81% yields. Selective oxidation of diols 3a and 3b was performed using a TEMPO, NaClO(2), NaOCl cocktail in 96% and 93% respective yields. This two-step process effectively furnished multigram amounts of enantiopure N-Boc-beta-hydroxyvaline 1a.