23202-81-5Relevant articles and documents
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Collins
, p. 403 (1968)
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A Novel Method for the Deoxygenation of Acetylated Sugars
Sano, Hiroshi,Takeda, Toshimitsu,Migita, Toshihiko
, p. 402 - 403 (1988)
The conversion of acetylated sugars 1 to deoxy sugars 2 by the action of triphenylsilane under homolytic conditions is reported.Both furanoses and pyranoses bearing an acetylated primary or seondary alcohol are effectively deoxygenated.
Synthesis of 1,2,3-tri-O-acetyl-5-deoxy-D-ribofuranose from D-ribose
Sairam, Pothukuchi,Puranik, Ramachandra,Sreenivasa Rao, Bhatraju,Veerabhadra Swamy, Ponnapalli,Chandra, Sharad
, p. 303 - 306 (2003)
A practical route towards the synthesis of 1,2,3-tri-O-acetyl-5-deoxy-D-ribofuranose from D-ribose is described. The key steps include deoxygenation of methyl 2,3-O-isopropylidene-5-O-sulfonyloxy-β-D-ribofuranoside by reductive displacement employing hydride reagents. Subsequent total hydrolysis followed by acetylation led to the title compound in 56% overall yield from D-ribose. The sequence is simple, inexpensive, high yielding and clearly suitable for multi-gram preparations.
Preparation method of high-purity capecitabine key intermediate
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, (2019/03/06)
The invention discloses a preparation method of a high-purity capecitabine key intermediate. The preparation method comprises the following steps: taking D-ribose as an initial raw material, performing hydroxyl protection, 5-site tosylation, reduction, deprotection and acetylation to obtain high-purity 1,2,3-O-triacetyl-5-deoxo-D-ribose, wherein the 5-site tosylation reaction is carried out in anorganic solvent 1 by adopting inorganic base 1. Meanwhile, the acetylation reaction is carried in the presence of alkali 2 by taking water as a reaction solvent and taking 4-dimethylamiopryidine as acatalyst. The preparation method disclosed by the invention is mild in reaction conditions, high in yield, economic and effective, the purity of the prepared 1,2,3-O-triacetyl-5-deoxo-D-ribose can reach 99.0%, the alpha-isomer is small in content even is not detected, and the preparation method is applicable to large-scale industrial production.
Synthesis of Nucleosides through Direct Glycosylation of Nucleobases with 5-O-Monoprotected or 5-Modified Ribose: Improved Protocol, Scope, and Mechanism
Downey, A. Michael,Pohl, Radek,Roithová, Jana,Hocek, Michal
, p. 3910 - 3917 (2017/03/27)
Simplifying access to synthetic nucleosides is of interest due to their widespread use as biochemical or anticancer and antiviral agents. Herein, a direct stereoselective method to access an expansive range of both natural and synthetic nucleosides up to a gram scale, through direct glycosylation of nucleobases with 5-O-tritylribose and other C5-modified ribose derivatives, is discussed in detail. The reaction proceeds through nucleophilic epoxide ring opening of an in situ formed 1,2-anhydrosugar (termed “anhydrose”) under modified Mitsunobu reaction conditions. The scope of the reaction in the synthesis of diverse nucleosides and other 1-substituted riboside derivatives is described. In addition, a mechanistic insight into the formation of this key glycosyl donor intermediate is provided.