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Volumn 46, Issue 9, 2010, Pages 1514-1516

Facilitated photochemical cleavage of benzylic C-O bond. Application to photolabile hydroxyl-protecting group design

Author keywords

[No Author keywords available]

Indexed keywords

BENZILIC ACID; CARBON; DIMETHYLAMINE; HYDROXYL GROUP; OXYGEN; TRITYL DERIVATIVE;

EID: 76949098298     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b922021f     Document Type: Article
Times cited : (25)

References (42)
  • 5
    • 68049115101 scopus 로고    scopus 로고
    • ed., M. Goeldner and R. S. Givens, Wiley-VCH, Weinheim, Germany
    • Dynamic Studies in Biology, ed., M. Goeldner, and, R. S. Givens, Wiley-VCH, Weinheim, Germany, 2005
    • (2005) Dynamic Studies in Biology
  • 27
    • 76949084727 scopus 로고    scopus 로고
    • note
    • It is known that the 9-phenylxanthen-9-yl (pixyl) group and 9-phenylthioxanthyl (S-pixyl) are photochemically removable to release primary alcohols and nucleosides; 9b-c
  • 30
    • 0003463148 scopus 로고    scopus 로고
    • ed., T. W. Greene and P. G. M. Wuts, Wiley-Interscience, New York, Quantum yields were determined by chemical actinometry
    • Protective Groups in Organic Synthesis, ed., T. W. Greene, and, P. G. M. Wuts, Wiley-Interscience, New York, 1999
    • (1999) Protective Groups in Organic Synthesis
  • 32
    • 76949105590 scopus 로고    scopus 로고
    • note
    • 2O (2:3) (cell 3). The monochromatic light centres at 285 nm and was opaque above 325 nm and below 250 nm 11c
  • 35
    • 76949105734 scopus 로고    scopus 로고
    • note
    • Photoreactions of 8 have been carried out in different solvents such as MeCN, MeCN/water, DMSO/water, acetone/water, benzene/water, chloroform, chloroform/water, and methanol. The reactions in methanol and MeCN/water (9:1) seemed to provide better results Irradiation of 6 in MeOH (5 mM) with 0.5% (v/v) chloroform for 20 min with the Pyrex-filtered light resulted in complete removal of the MMTr group. Under the same reaction conditions, the Tr group could not be removed from 5, even after increasing chloroform in methanol to 10%. However, deprotection of Tr was observed after 20 min irradiation with a 3-phenylpropanol/5 ratio of 0.06:1 in MeOH/chloroform (1:1) and 0.15:1 in MeOH/chloroform (1:9). When these irradiated reaction solutions were kept in dark, the deprotection reactions gradually reached completion overnight, which clearly indicates the existance of photogenerated acidic substance(s) catalyzing the reactions. Furthermore, in control experiments, there was no sign of photoreactions when 5 and 6 were irradiated with the Pyrex-filtered light in MeOH, MeCN/water, chloroform, or MeCN/chloroform Utilization of photogenerated acids from sensitizers in protecting group installation have been recently reported, albeit the identity of some acids are not clear; 15b-c


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.