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Volumn , Issue 10, 1997, Pages 1146-1150

Convenient procedures for the synthesis of N-BOC-D-serinal acetonide from L-serine

Author keywords

(R) Garner's aldehyde; Interconversion of functional groups; L serine; N protected amino aldehydes; Stereocontrolled organic synthesis

Indexed keywords

ALPHA AMINO ACID; N BOC SERINAL ACETONIDE; SERINE; SERINE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0030818943     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-3186     Document Type: Article
Times cited : (30)

References (42)
  • 4
    • 0030583508 scopus 로고    scopus 로고
    • For several examples on asymmetric reactions with L-serinal (1), see: Michael-type addition (stereocontrolled sequential functionalization): Hanessian, S.; Wang, W.; Gai, Y. Tetrahedron Lett. 1996, 37, 7477.
    • (1996) Tetrahedron Lett. , vol.37 , pp. 7477
    • Hanessian, S.1    Wang, W.2    Gai, Y.3
  • 19
  • 35
    • 34547391096 scopus 로고    scopus 로고
    • note
    • 3.
  • 36
    • 34547390196 scopus 로고    scopus 로고
    • note
    • Another protective group (tert-butyldimethylsilyl) for the hydroxy substituent of L-serine (3) was tested. This group could not be used in the total synthesis of 2 since it caused several problems in the formation of the oxazolidine ring due to the action of an acid medium, which produced hydrolysis of the O-Si bond.
  • 42
    • 34547390233 scopus 로고    scopus 로고
    • note
    • Duplication of some signals in the NMR spectra was observed due to nitrogen inversion.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.