A practical synthesis of 2-deoxy-2-fluoro-D-arabinofuranose derivatives.
Тип публикации: Journal Article
Дата публикации: 1975-07-01
SCImago Q2
WOS Q2
БС2
SJR: 0.483
CiteScore: 4
Impact factor: 2.5
ISSN: 00086215, 1873426X
PubMed ID:
1139559
Organic Chemistry
Biochemistry
General Medicine
Analytical Chemistry
Краткое описание
A seven-step synthesis of 1,3-di-O-acetyl-5-O-benzoyl-2-deoxy-2-fluoro-D-arabinofuranose, a versatile intermediate in the synthesis of chemotherapeutically important nucleosides, was achieved from 1,2:5,6-di-O-isopropylidene-3-O-tosyl-alpha-D-allofuranose. The crucial steps were the fluorination by use of potassium fluoride in acetamide and the conversion of 6-O-benzoyl-3-deoxy-3-fluoro-D-glucofuranose into 5-O-benzoyl-2-deoxy-2-fluoro-3-O-formyl-D-arabinofuranose by periodate oxidation. Also described is the synthesis of 1-(2-deoxy-2-fluoro-beta-D-arabinofuranosyl)cytosine. This procedure affords good overall yields of products without formation of undesirable, isomeric intermediates and is suitable for large-scale preparations.
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Метрики
72
Всего цитирований:
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ГОСТ
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Reichman U., Watanabe K. A., FOX J. J. A practical synthesis of 2-deoxy-2-fluoro-D-arabinofuranose derivatives. // Carbohydrate Research. 1975. Vol. 42. No. 2. pp. 233-240.
ГОСТ со всеми авторами (до 50)
Скопировать
Reichman U., Watanabe K. A., FOX J. J. A practical synthesis of 2-deoxy-2-fluoro-D-arabinofuranose derivatives. // Carbohydrate Research. 1975. Vol. 42. No. 2. pp. 233-240.
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RIS
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TY - JOUR
DO - 10.1016/S0008-6215(00)84265-2
UR - https://doi.org/10.1016/S0008-6215(00)84265-2
TI - A practical synthesis of 2-deoxy-2-fluoro-D-arabinofuranose derivatives.
T2 - Carbohydrate Research
AU - Reichman, Uri
AU - Watanabe, Kyoichi A.
AU - FOX, Jack J.
PY - 1975
DA - 1975/07/01
PB - Elsevier
SP - 233-240
IS - 2
VL - 42
PMID - 1139559
SN - 0008-6215
SN - 1873-426X
ER -
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BibTex (до 50 авторов)
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@article{1975_Reichman,
author = {Uri Reichman and Kyoichi A. Watanabe and Jack J. FOX},
title = {A practical synthesis of 2-deoxy-2-fluoro-D-arabinofuranose derivatives.},
journal = {Carbohydrate Research},
year = {1975},
volume = {42},
publisher = {Elsevier},
month = {jul},
url = {https://doi.org/10.1016/S0008-6215(00)84265-2},
number = {2},
pages = {233--240},
doi = {10.1016/S0008-6215(00)84265-2}
}
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MLA
Скопировать
Reichman, Uri, et al. “A practical synthesis of 2-deoxy-2-fluoro-D-arabinofuranose derivatives..” Carbohydrate Research, vol. 42, no. 2, Jul. 1975, pp. 233-240. https://doi.org/10.1016/S0008-6215(00)84265-2.
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