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Volumn 1996, Issue 12, 1996, Pages 1176-1178

Baker's Yeast Mediated Biohydrogenation of 2-Substituted Allyl Alcohols: Synthesis of Enantiomerically Pure (2S)-3-Benzyloxy-2-methyl-1-propanol

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EID: 0003290522     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5708     Document Type: Article
Times cited : (10)

References (23)
  • 4
    • 1542678493 scopus 로고    scopus 로고
    • note
    • We also carried out an alternative synthesis of the silyl ether 3b starting from commercially available glycerol acetonide. This relatively trivial approch was quite satisfactory and proceeded in 4 steps with 35% yield. We decided to explore also the relatively new and more intriguing elaboration of DHAD that holds promises of future developments.
  • 6
    • 0017889042 scopus 로고
    • For instance, the DHA monoacetate is long known and its preparation (30% yield) requires careful experimental conditions; see: Gettys, G. A.; Gutsche, C. D. Bioorg. Chem. 1978, 7, 141.
    • (1978) Bioorg. Chem. , vol.7 , pp. 141
    • Gettys, G.A.1    Gutsche, C.D.2
  • 8
    • 1542783847 scopus 로고    scopus 로고
    • note
    • We were able to prepare the monoester 4b by controlled esterification of DHA or hydrolysis of the dibenzoate 4c, thus lowering the yield of the process.
  • 9
    • 1542468995 scopus 로고    scopus 로고
    • note
    • The selective preparation of a monosilyl ether of 4a would allow the preparation of the compound 3b as an intermediate of the benzyl ether 2a. However, the monosilylation of 4a as well as the hydrolysis of 4d to a monosilyl derivative were unsatisfactory.
  • 12
    • 1542573561 scopus 로고    scopus 로고
    • note
    • 2=C), 7.40-7.60 (m, 5 H, Ar).
  • 18
    • 0028067680 scopus 로고
    • Compound 7c is obtained as a mixture of cis- and trans-isomers that could be separated by column chromatography. Similarly, it has been possible to isolate the single isomers of acetal 7b and determine their structure by X-ray chrystallography (Waagen, V.; Barua, T. K.; Anthonsen, H. W.; Hansen, L. K.; Fossli, D.-J.; Hough, E.; Anthonsen, T. Tetrahedron 1994, 50, 10055). For the next hydrolytic step, however, the isomeric mixture of 7c was directly used as such.
    • (1994) Tetrahedron , vol.50 , pp. 10055
    • Waagen, V.1    Barua, T.K.2    Anthonsen, H.W.3    Hansen, L.K.4    Fossli, D.-J.5    Hough, E.6    Anthonsen, T.7
  • 19
    • 1542468994 scopus 로고    scopus 로고
    • note
    • 2O), 7.30-7.60 (m, 5 H, Ar).
  • 20
    • 1542468997 scopus 로고    scopus 로고
    • note
    • D +2.95 (c 2.2 in ethanol). The chemico-physical properties are as reported in the Ref. 2.
  • 21
    • 1542573560 scopus 로고    scopus 로고
    • note
    • When the incubation was carried out for a longer time (21 days) we isolated also (2R)-3-benzyloxy-2-methyl-propanoic acid. The configuration and enantiomeric excess (96%) of this compound was established by its reduction to the optically pure (25)-alcohol.
  • 22
    • 1542678492 scopus 로고    scopus 로고
    • note
    • 2OCO appeared as three groups of signals at 4.23-4.27, 4.27-4.34 and 4.34-4.39 ppm (1:2:1 ratio) in the racemic compound. In the spectrum of the optically active 1a the signals betwen 4.27 and 4.34 ppm were not detectable.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.