- Synthesis of Deoxyglycosides by Desulfurization under UV Light
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This study was performed to develop a highly efficient method whereby desulfurization could be completed in 0.5 h under ultraviolet light, at room temperature, and in the presence of trialkylphosphine. Using this method, deoxyglycosides could be produced from sulfur-containing glycosides in almost quantitative yields. The much higher reactivity of desulfurization with triethylphosphine versus that with triethylphosphite is also discussed.
- Ge, Jian-Tao,Li, Ying-Ying,Tian, Jun,Liao, Rong-Zhen,Dong, Hai
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p. 7008 - 7014
(2017/07/15)
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- From glycoside hydrolases to thioglycoligases: The synthesis of thioglycosides
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The treatment of various glycosyl acceptors, each containing a reactive thiol group, with the appropriate glycosyl donor and a glycoside hydrolase or glycosynthase, failed to yield any thioglycosides - only the products of O-glycosylation were formed. However, thioglycosides were formed when a thioglycoligase was used to mediate the reaction between acceptor and donor. In fact, pyranose acceptors possessing a thiol group at C3, C4 or C6 (but not C2) were all capable of conversion into thioglycosides. Some comment is given regarding the mechanism of the various processes.
- Stick, Robert V.,Stubbs, Keith A.
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p. 321 - 335
(2007/10/03)
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- TOTAL ASYMMETRIC SYNTHESES OF 3- AND 4-DEOXY-HEXOSES AND DERIVATIVES.
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(1S,4S)-7-Oxabicyclohept-5-en-2-one ((-)-5, a "naked sugar") has been converted to (-)-(1R,4S,6S)-6-endo-benzyloxy-2-bromo-7-oxabicyclohept-2-ene ((-)-12) in a highly stereoselective fashion.Double hydroxylation of the C=C double bond of (-)
- Fattori, Daniela,Vogel, Pierre
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p. 10587 - 10602
(2007/10/02)
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- SYNTHESIS OF SOME DEOXY, UNSATURATED, AND DIDEOXY SUGARS VIA REGIOSELECTIVE THIOACYLATION OF GLYCOPYRANOSIDES BY THE DIBUTYLTIN OXIDE METHOD
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Treatment of non-protected glycopyranosides (Me α-D-Glc, Me β-D-Glc, Me α-D-Xyl, and Me β-D-Xyl) with dibutyltin oxide followed by thioacylation with phenoxythiocarbonyl chloride gave the mono-thionocarbonates regioselectively in high yields.Acetylation o
- Haque, Md. Ekramul,Kikuchi, Tohoru,Kanemitsu, Kimihiro,Tsuda, Yoshisuke
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p. 430 - 433
(2007/10/02)
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- SYNTHESIS OF 4-DEOXY-D-xylo-HEXOSE AND 4-AZIDO-4-DEOXY-D-GLUCOSE AND THEIR EFFECTS ON LACTOSE SYNTHASE
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Syntheses are reported of 4-deoxy-D-xylo-hexose and 4-azido-4-deoxy-D-glucose as potential inhibitors for lactose synthase.These syntheses involved S
- Sinha, Sudhir K.,Brew, Keith
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p. 239 - 248
(2007/10/02)
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- ACID-CATALYSED MONOACETYLATION OF TWO 3-DEOXYHEXITOLS
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Acid-catalysed monobutylidenation of 3-deoxy-D-ribo-hexitol yields the 2,4-acetal as the sole, detected product. 3-Deoxy-L-xylo-hexitol yields the 4,5-acetals as kinetic products, and the 4,6-acetal as the thermodynamic product.
- Bonner, Trevor G.,Gibson, David,Lewis, David
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p. 243 - 248
(2007/10/02)
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