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Volumn 71, Issue 24, 2006, Pages 9045-9050

Aqueous phosphoric acid as a mild reagent for deprotection of tert-butyl carbamates, esters, and ethers

Author keywords

[No Author keywords available]

Indexed keywords

ESTERS; ETHERS; KETONES; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

EID: 33751571632     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo061377b     Document Type: Article
Times cited : (85)

References (62)
  • 3
    • 85088189214 scopus 로고    scopus 로고
    • Facts and Figures for the Chemical Industry
    • Facts and Figures for the Chemical Industry. Chem. Eng. News 2003, 81, 25.
    • (2003) Chem. Eng. News , vol.81 , pp. 25
  • 5
    • 0003601534 scopus 로고    scopus 로고
    • Budavari, S., O'Neil, M. J., Smith, A., Heckelman, P., Kinneary, J. F., Eds.; Merck & Co., Inc.: Whitehouse Station, NJ
    • The Merck Index, 12th ed.; Budavari, S., O'Neil, M. J., Smith, A., Heckelman, P., Kinneary, J. F., Eds.; Merck & Co., Inc.: Whitehouse Station, NJ, 1996.
    • (1996) The Merck Index, 12th Ed.
  • 17
    • 33947466828 scopus 로고
    • Aqueous 80 wt% phosphoric acid effectively hydrated 4-isoprenephenol: Bader, A. R.; Bean, W. C. J. Am. Chem. Soc. 1958, 3073.
    • (1958) J. Am. Chem. Soc. , pp. 3073
    • Bader, A.R.1    Bean, W.C.2
  • 32
    • 33751578565 scopus 로고    scopus 로고
    • note
    • For the reaction workup, the reaction mixture was reversely quenched into a mixture of TEA/water/2-MeTHF. This was done to avoid polymerization of the product observed using the forward quench method.
  • 36
    • 33751580362 scopus 로고    scopus 로고
    • note
    • Use of anhydrous hydrogenolysis conditions did not work well for this deprotection.
  • 37
    • 33751575136 scopus 로고    scopus 로고
    • note
    • t intermediate was observed. Nonetheless, the reaction was quenched after the completion of the cladinose hydrolysis due to formation of other impurities (i.e., cleavage of the desosamine sugar).
  • 39
    • 33751555955 scopus 로고    scopus 로고
    • note
    • 4 reaction condition with limited exceptions, although we also found few exceptions.
  • 53
    • 33751554931 scopus 로고    scopus 로고
    • note
    • 4 at room temperature.
  • 60
    • 33751558864 scopus 로고    scopus 로고
    • note
    • 4 were used so that adequate stirring of the mixture could be ensured.
  • 61
    • 33751563956 scopus 로고    scopus 로고
    • note
    • 4 (15 equiv) was needed.
  • 62
    • 14644419027 scopus 로고    scopus 로고
    • 2 appears to be another economical option when no other acid-sensitive groups are present: Strazzolini, P.; Misuri, N.; Polese, P. Tetrahedron Lett. 2005, 46, 2075-2078.
    • (2005) Tetrahedron Lett. , vol.46 , pp. 2075-2078
    • Strazzolini, P.1    Misuri, N.2    Polese, P.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.