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Volumn , Issue 11, 1996, Pages 1801-1810

Synthesis of protected enantiopure erythrulose derivatives

Author keywords

Ascorbic acid as chiron; Erythrulose, protected derivatives; Isoascorbic acid as chiron; Monosaccharides

Indexed keywords


EID: 33748899259     PISSN: 09473440     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article
Times cited : (29)

References (59)
  • 1
    • 3843090366 scopus 로고
    • (Ed.: R. Scheffold), Salle & Sauerländer Verlag, Frankfurt
    • [1a] A. Vasella in Modern Synthetic Methods 1980 (Ed.: R. Scheffold), Salle & Sauerländer Verlag, Frankfurt, 1980, p. 173-267.
    • (1980) Modern Synthetic Methods 1980 , pp. 173-267
    • Vasella, A.1
  • 4
    • 0021689546 scopus 로고
    • [1d] T. D. Inch, Tetrahedron 1984, 40, 3161-3213.
    • (1984) Tetrahedron , vol.40 , pp. 3161-3213
    • Inch, T.D.1
  • 41
    • 33748893276 scopus 로고    scopus 로고
    • note
    • [7a]. For this reason, all erythrulose derivatives prepared subsequently, including the D series, always carried the TBDPS group.
  • 48
    • 33748913785 scopus 로고    scopus 로고
    • note
    • Erythrulose derivatives are prone to a slow epimerization with the consequent loss of optical purity. We therefore prepared them just prior to use by oxidation of the appropriate precursor.
  • 51
    • 33748901705 scopus 로고    scopus 로고
    • note
    • One could envisage in principle to perform the same reaction sequences on 8 as the starting material. However, in the course of these reactions C-5 of 7 becomes eventually the carbonyl group of the target L-erythrulose derivative. Consequently, since 7 and 8 only differ in the configuration at C-5, the reaction sequences would afford in both cases L-erythrulose derivatives.
  • 58
    • 33748908272 scopus 로고    scopus 로고
    • note
    • [14] had to be used here, as the Swern method gave low yields and partial decomposition.
  • 59
    • 33748913966 scopus 로고    scopus 로고
    • note
    • With the signal-to-noise ratio observed in the NMR measurements, even 1% of the diastereomeric ketone would have been detected.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.