메뉴 건너뛰기




Volumn 15, Issue 1, 2011, Pages 249-257

Scale-up of a chemo-biocatalytic route to (2 R,4 R)- and (2 S,4 S)-monatin

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOADDITION REACTION; DIASTEREOMERIC; ENANTIOPURE; MONATIN; NATURAL SWEETENER; SCALE-UP;

EID: 79251486667     PISSN: 10836160     EISSN: 1520586X     Source Type: Journal    
DOI: 10.1021/op1001947     Document Type: Article
Times cited : (17)

References (27)
  • 19
    • 0004235357 scopus 로고
    • 2nd ed.; John Wiley and Sons, Inc.: London,; Collective
    • In Organic Syntheses, 2nd ed.; Gillman, H.; Blatt, A. H., Eds., John Wiley and Sons, Inc.: London, 1958; Collective Vol. 1.
    • (1958) Organic Syntheses , vol.1
    • Gillman, H.1    Blatt, A.H.2
  • 20
    • 79251500078 scopus 로고    scopus 로고
    • Merck, AR grade, containing 0.03% (m/m) water.
    • Merck, AR grade, containing 0.03% (m/m) water.
  • 21
    • 33845550921 scopus 로고
    • Ethyl 2-chloro-2-(hydroxyimino)acetate (8) is commercially available in bulk from a number of suppliers; however, costs associated with the purchase and shipping of (8) (US $400-700/kg) prompted us to synthesise the material in-house.
    • Kozikowski, P.; Adamczyk, M. J. Org. Chem. 1983, 48, 366-372 Ethyl 2-chloro-2-(hydroxyimino)acetate (8) is commercially available in bulk from a number of suppliers; however, costs associated with the purchase and shipping of (8) (US $400-700/kg) prompted us to synthesise the material in-house.
    • (1983) J. Org. Chem. , vol.48 , pp. 366-372
    • Kozikowski, P.1    Adamczyk, M.2
  • 22
    • 79251516839 scopus 로고    scopus 로고
    • note
    • The yield of (8) on 150 g scale or less was found to be slightly higher, at an average of 56%. However, all reactions carried out at a scale of 200-500 g afforded lower yields of (8), with an average yield of 43% obtained on this scale.
  • 25
    • 0037023419 scopus 로고    scopus 로고
    • note
    • Personal communication with J. Lalonde, Y. Yao, and Y. Wang of Altus Biologics Inc., who selected the enzyme for this resolution, see ref 7a. The ChiroCLEC-BL was supplied by Altus Biologics from a single batch, and the resolution was run five times on this scale. Although ChiroCLEC-BL is no longer commercially available on this scale, the nonimmobilized form of the enzyme, alcalase, which is commercially available, performed equally well in this transformation on laboratory scale. For another example of the use of the ChiroCLEC-BL in synthesis see: Ema, T.; Jittani, M.; Furuie, K.; Utaka, M.; Sakai, T. J. Org. Chem. 2002, 67, 2144-2151
    • (2002) J. Org. Chem. , vol.67 , pp. 2144-2151
    • Ema, T.1    Jittani, M.2    Furuie, K.3    Utaka, M.4    Sakai, T.5
  • 26
    • 79251509333 scopus 로고    scopus 로고
    • note
    • 1H NMR spectrum was no longer present.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.