- A mild and rapid glycosylation reaction between pyrimidine bases and 2-deoxyribofuranosyl N,N,N',N'-tetramethylphosphoroamidates
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A trimethylsilyl triflate-mediated coupling reaction to produce protected 2′-deoxynucleosides has been developed by using N,N,N',N'-tetramethylphosphoroamidate as a leaving group. In this reaction, employment of a 3,4,5-trimethoxybenzoyl group as the 3-hydroxyl protective group in the sugar moiety improved the β-stereoselectivity via a novel 1,3-participation.
- Iimori, Takamasa,Kobayashi, Hiroshi,Hashimoto, Shun-Ichi,Ikegami, Shiro
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p. 485 - 488
(2007/10/03)
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- Stereoselective synthesis of α-linked 2-deoxysaccharides and furanosaccharides by the use of 2-deoxy 2-pyridyl-1-thio pyrano- and furanosides as donors and methyl iodide as an activator
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A practical and highly stereoselective glycosidation methodology is described, where anomeric mixture of 2-deoxy 2-pyridyl-1-thiopyranoside donors (1-3,27) have been coupled with several sugar alcohols (4-8,29,31) on activation by methyl iodide to obtain axially linked 2-deoxysaccharides (9-17,30,32,33). Application of this method for the synthesis of disaccharide fragment 28 of avermectin is also described. Utility of this method is also shown by use of 2-pyridyl-1-thiofuranosides (34-36) as donors to prepare α-linked furanosides (42-51).
- Mereyala,Kulkarni,Ravi,Sharma,Rao,Reddy
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p. 545 - 562
(2007/10/02)
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- Improved procedure for the regiospecific synthesis of 2'-deoxyribonucleosides
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2'-Deoxyribonucleosides are regiospecifically synthesized in high yields by catalyzing with KI-dibenzo-18-crown-6 PTC the condensation between unprotected silylated purines and pyrimidines and the appropriate easily available 2-deoxy-ribofuranosyl or pyranosyl sugar derivatives.
- Baud,Chavis,Lucas,Imbach
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p. 4437 - 4440
(2007/10/02)
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- 5(S), 6(R)-5, 7-DIBENZOYLOXY-6-HYDROXYHEPTANOATE ESTER : IMPROVED SYNTHESIS OF A LEUKOTRIENE INTERMEDIATE
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The title compound, a key intermediate in the synthesis of leukotriene A4, was prepared by a convenient procedure from 2-deoxy-D-ribose.
- Marriott, D. P.,Bantick, J. R.
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p. 3657 - 3658
(2007/10/02)
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