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Volumn 639, Issue , 1996, Pages 105-116

Efficient Synthetic Routes to Chiral 6-Deoxy-6,6,6-trifluorosugars via Intramolecular 1,2-O,O-Silyl Migration

Author keywords

[No Author keywords available]

Indexed keywords


EID: 1842421272     PISSN: 00976156     EISSN: None     Source Type: Book Series    
DOI: 10.1021/bk-1996-0639.ch008     Document Type: Article
Times cited : (3)

References (73)
  • 9
    • 85088543459 scopus 로고    scopus 로고
    • note
    • 3 derivatives with almost complete retention of configuration as well as high chemoselectivity. See, the references 10 and 11.
  • 40
    • 1842436047 scopus 로고    scopus 로고
    • note
    • Calculations were performed by MOPAC v 6.10 (AM1) implemented in CAChe Worksystem (SONY/Tektronix Corporation) for the conformers obtained from the rigid search method followed by the optimization by the eigenvector following minimization (EF) method with the extra keyword "PRECISE", final gradient norm being less than 0.01 kcal/Å.
  • 41
    • 1842436048 scopus 로고    scopus 로고
    • note
    • - (MNDO: 1.735 Å, AM1: 1.654 Å, PM3: 1.918 Å), to the one obtained by ab initio calculations (HF/3-21G: 1.523 Å, HF/6-31G*: 1.529 Å, MP2/6-31G*: 1.529 Å). MOPAC, in the calculation of this alkoxide, tends to give longer and shorter bond lengths for C-C and C-O with the difference of 0.13∼0.39 Å and 0.04∼0.06 Å, respectively.
  • 47
    • 1842488366 scopus 로고    scopus 로고
    • note
    • Reaction temperature would also be the important factor because, as shown in the text, LAH reduction was conducted at 0°C, while the mixture was cooled to -78°C for DIBALH reduction.
  • 58
    • 1842488365 scopus 로고    scopus 로고
    • Sugar numbering system was used
    • Sugar numbering system was used.
  • 70
    • 1842540386 scopus 로고    scopus 로고
    • unpublished data. The details will be published elsewhere
    • Yamazaki, T.; Oniki, T.; Kitazume,T. unpublished data. The details will be published elsewhere.
    • Yamazaki, T.1    Oniki, T.2    Kitazume, T.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.