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Volumn 54, Issue 32, 1998, Pages 9341-9356

Enzymatic desymmetrization of prochiral 2-benzyl-1,3-propanediol derivatives: A practical chemoenzymatic synthesis of novel phosphorylated tyrosine analogues

Author keywords

Amino acids and derivatives; Asymmetric synthesis; Enzymes and enzymatic reaction; Phosphonic acid and derivatives

Indexed keywords

PHENYLALANINE DERIVATIVE; PHOSPHONIC ACID DERIVATIVE; TYROSINE DERIVATIVE;

EID: 0032491025     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)00586-9     Document Type: Article
Times cited : (32)

References (45)
  • 25
    • 0024464541 scopus 로고
    • 11. Recent examples for lipase-catalyzed desymmetrization of prochiral 2-substituted 1,3-propanediols: a)Tsuji, K.; Terao, Y.; Achiwa, K. Tetrahedron Lett. 1989, 30, 6189.
    • (1989) Tetrahedron Lett. , vol.30 , pp. 6189
    • Tsuji, K.1    Terao, Y.2    Achiwa, K.3
  • 32
    • 0010456807 scopus 로고    scopus 로고
    • note
    • 9c However, the method was not available for the preparation in multi-gram scale due to the unpredictable exothermic reaction. This alternative method allows us to prepare 9b in a multi-gram scale, readily.
  • 34
    • 0010455389 scopus 로고    scopus 로고
    • note
    • 17 The coupling patterns of the methylene signals α to the MTPA esters are consistent with the arguments of Yamaguchi.
  • 36
    • 0010452048 scopus 로고    scopus 로고
    • note
    • 18. Over-hydrolysis products 4a,b were usually produced in 10-20% yield. To prevent the over-hydrolysis, enantioselective hydrolysis with various lipases including PPL, CCL and CHIRAZYME®s L-1∼L-4 (Boehringer Mannheim) were examined. However, lipase PS was found to be the best catalyst for this transformation with respect to enantioselectivity and yield. The authors wish to thank Dr. K. Tateno of Boehringer Mannheim Japan for the generous gift of the CHIRAZYME®s.
  • 39
    • 0010524118 scopus 로고    scopus 로고
    • note
    • 21. Since the Curtius rearrangements of 11a,b with 2-methyl-2-propanol under the conditions gave 13a,b in low yield, the transcarbamation reactions were necessary to obtain a good yield of 13a,b.
  • 40
    • 0010455390 scopus 로고    scopus 로고
    • note
    • 3) analysis of the corresponding MTPA esters derived from (R)- and (S)-MTPA.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.