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Volumn , Issue 3, 2004, Pages 493-496

Simple and Efficient Routes to Optically Active chiro- and allo-Inositol Derivatives from myo-Inositol

Author keywords

Carbohydrates; Cyclitols; Inhibitors; Inositols; Regioselectivity

Indexed keywords

1,2:4,5 DI O ISOPROPYLIDENE INOSITOL; 1,6:3,4 DI O ISOPROPYLIDENE INOSITOL; CARBAMIC ACID; INOSITOL DERIVATIVE; UNCLASSIFIED DRUG;

EID: 1442286556     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-815443     Document Type: Article
Times cited : (11)

References (50)
  • 7
    • 0031008911 scopus 로고    scopus 로고
    • and references cited therein
    • (c) Chida, N.; Ogawa, S. Chem. Commun. 1997, 807; and references cited therein.
    • (1997) Chem. Commun. , pp. 807
    • Chida, N.1    Ogawa, S.2
  • 33
    • 0035917329 scopus 로고    scopus 로고
    • Although optically active inositol derivatives can be made from sugar derivatives via Ferrier type cyclization, the yield of such C-C coupling is known to vary greatly. Also synthetic steps become too lengthy. But recently an elegant synthesis of all inositol derivatives in optically pure form via Ferrier cyclization followed by stereoselective reduction was reported, see: (a) Takahashi, H.; Kittaka, H.; Ikegami, S. J. Org. Chem. 2001, 66, 2705. (b) Takahashi, H.; Kittaka, H.; Ikegami, S. Tetrahedron Lett. 1998, 39, 9707.
    • (2001) J. Org. Chem. , vol.66 , pp. 2705
    • Takahashi, H.1    Kittaka, H.2    Ikegami, S.3
  • 34
    • 0032564589 scopus 로고    scopus 로고
    • Although optically active inositol derivatives can be made from sugar derivatives via Ferrier type cyclization, the yield of such C-C coupling is known to vary greatly. Also synthetic steps become too lengthy. But recently an elegant synthesis of all inositol derivatives in optically pure form via Ferrier cyclization followed by stereoselective reduction was reported, see: (a) Takahashi, H.; Kittaka, H.; Ikegami, S. J. Org. Chem. 2001, 66, 2705. (b) Takahashi, H.; Kittaka, H.; Ikegami, S. Tetrahedron Lett. 1998, 39, 9707.
    • (1998) Tetrahedron Lett. , vol.39 , pp. 9707
    • Takahashi, H.1    Kittaka, H.2    Ikegami, S.3
  • 48
    • 1442318912 scopus 로고    scopus 로고
    • note
    • This compound did not melt on heating but charred in the temperature range 110-130°C.
  • 50
    • 1442269740 scopus 로고    scopus 로고
    • note
    • 4) and evaporated. The crude mixture of 3D and 4D thus obtained was dissolved in DMA (7 mL) and reacted with KOAc (500 mg, 5 mmol) at 70-80°C for 5 h. DMA was evaporated and usual work-up of the residue followed by column chromatography yielded 5L (124 mg, 41%) and 8D (186 mg, 54%).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.