ABSOLUTE-CONFIGURATION OF (2-AMINO-1-HYDROXYETHYL)PHOSPHONIC ACID FROM ACANTHAMOEBA-CASTELLANII (NEFF) - PREPARATION OF PHOSPHONIC ACID ANALOGS OF (+)-SERINE AND (-)-SERINE
ABSOLUTE-CONFIGURATION OF (2-AMINO-1-HYDROXYETHYL)PHOSPHONIC ACID FROM ACANTHAMOEBA-CASTELLANII (NEFF) - PREPARATION OF PHOSPHONIC ACID ANALOGS OF (+)-SERINE AND (-)-SERINE
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DOI：
10.1002/jlac.1989198901101
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发表时间：
1989-06-01
期刊：
影响因子：
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通讯作者：
VOLLENKLE, H
中科院分区：
文献类型：
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作者：
HAMMERSCHMIDT, F;VOLLENKLE, H
[（2-（苄氧基）-1-羟乙基）膦酸二甲酯] [rac-（7）]用二聚内半缩醛（+）-8衍生，得到色谱可分离的非对映异构体9和10。在酸性条件下除去手性助剂，得到对映体膦酸酯（-）-和（+-）-7，e.e.≥百分之九十八基于氨基甲酸酯12的X射线分析，膦酸酯（+）-7具有（S）-构型。（+）-和（-）-7转化为（2-氨基-1-羟乙基）膦酸（+）-和（-）-（1）。后者也是从卡氏阿米巴（Neff）中分离得到的，具有（R）-构型。（+）-和（-）-7用三苯基膦/DEAD/HN_3处理，得到叠氮膦酸酯（-）-和（+）-16，其经催化还原和去封闭后得到丝氨酸的膦酸类似物（+）-和（-）-4。
Dimethyl [(2-(benzyloxy)-1-hydroxyethyl)phosphonate] [rac-(7)] was derivatised with dimeric lactol (+)-8 to give the chromatographically separable diastereomers 9 and 10. By removing the chiral auxiliary under acidic conditions, the enantiomeric phosphonates (-)- and (+-)-7 were obtained with e.e. .gtoreq. 98%. On the basis of an X-ray analysis of urethane 12 the phosphonate (+)-7 has (S)-configuration. (+)- and (-)-7 were transformed into (2-amino-1-hydroxyethyl)phosphonic acids (+)- and (-)-(1). The latter was also isolated from Acanthamoeba castellanii (Neff) and has (R)-configuration. (+)- and (-)-7 were treated with triphenylphosphane/DEAD/HN3 to give azidophosphonates (-)- and (+)-16, which after catalytic reduction and deblocking gave the phosphonic acid analogues (+)- and (-)-4 of serine.