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Volumn 52, Issue 23, 2011, Pages 3045-3047

An unexpected migration of O-silyl group under Mitsunobu reaction conditions

Author keywords

1,4 O O Silyl migration; Amino alcohols; Carbohydrates; N Nucleophiles; Nucleophilic substitution

Indexed keywords

1,2:3,4 DI O ISOPROPYLIDENE DEXTRO PSICOFURANOSE; 2 HYDROXYETHYL TRIALKYLSILYLETHER DERIVATIVE; ALCOHOL; ALKENE; ANTIDIABETIC AGENT; ETHER DERIVATIVE; FRUCTOSE; IMINOSUGAR; NUCLEOPHILE; PHTHALIMIDE; PHYTOSPHINGOSINE; UNCLASSIFIED DRUG;

EID: 79955665845     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.04.015     Document Type: Article
Times cited : (14)

References (50)
  • 36
    • 79955674974 scopus 로고    scopus 로고
    • The numbers were assigned based on the starting material fructose
    • The numbers were assigned based on the starting material fructose.
  • 37
    • 79955660673 scopus 로고    scopus 로고
    • note under CCDC refno. 801190 and 801191, respectively
    • 3, Z = 4, Mo Kα radiation (λ = 0.71073 ), T = 100(2) K; R1 = 0.0626, wR2 = 0.1556 (I >2σ(I)); R1 = 0.0667, wR2 = 0.1589 (all data). The CIF file for the crystal data of compound 8 and 16 is available from the Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif under CCDC ref no. 801190 and 801191, respectively.
  • 38
    • 79955656656 scopus 로고    scopus 로고
    • Hydrogen atoms were removed for clarity of the structure
    • Hydrogen atoms were removed for clarity of the structure.
  • 39
    • 0033529819 scopus 로고    scopus 로고
    • A similar kind of intermediate has been found in the azidation of 1,2 and 1,3-diols by azidotrimethylsilane via a Mitsunobu reaction to give C-2 and C-3 azides, respectively. It is also noticed that the selectivity depends on the surrounding sterichindrance of the C-2 or C-3 alcohol. L. He, M. Wanunu, H.-S. Byun, and R. Bittmann J. Org. Chem. 64 1999 6049
    • (1999) J. Org. Chem. , vol.64 , pp. 6049
    • He, L.1    Wanunu, M.2    Byun, H.-S.3    Bittmann, R.4
  • 41
    • 79955650191 scopus 로고    scopus 로고
    • note
    • 3P and 6a in THF with water. This intermediate was further confirmed by observing a downfield shift of C1 protons in the corresponding C1-O-acetylated derivative. Where as a downfield shift of C2 proton was observed in C2-O-acetylated derivative of compound 6a.
  • 50
    • 79955667717 scopus 로고    scopus 로고
    • note
    • 3P (781.6 mg, 2.98 mmol) and phthalimide (175.3 mg, 1.19 mmol) in dry THF (8 mL) at 0 °C was injected DIAD (602 mg, 2.98 mmol) dropwise. The reaction mixture was allowed to stir at 25 °C for 6 h. After completion of reaction (by TLC) the mixture was concentrated and the product was purified by column chromatography using ethyl acetate: hexane (1:9) to give compound 8 (322 mg, 75%) as a colorless liquid.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.