72396-00-0Relevant academic research and scientific papers
Synthesis of protected glucose derivatives from levoglucosan by development of common carbohydrate protecting group reactions under continuous flow conditions
Marion, Keevan C.,Wooke, Zachary,Pohl, Nicola L.B.
, p. 23 - 29 (2018/08/21)
Common carbohydrate protecting group reactions under continuous flow processes are reported in the context of producing partially-protected glucose building blocks from levoglucosan. Benzyl ether protection was demonstrated without the use of NaH using ba
Synthesis of α-glycosyl thiols by stereospecific ring-opening of 1,6-anhydrosugars
Zhu, Xiangming,Dere, Ravindra T.,Jiang, Junyan,Zhang, Lei,Wang, Xiaoxia
, p. 10187 - 10197 (2012/02/05)
Treatment of 1,6-anhydrosugars with commercially available bis(trimethylsilyl) sulfide in the presence of trimethylsilyl triflate led to the formation of α-glycosyl thiols. All the reactions were highly stereoselective and afforded the α-glycosyl thiols in good to excellent yields. By this procedure, a variety of 1,6-anhydrosugars, differing in their sugar units, glycosidic linkages, and protecting group pattern, were converted smoothly into the corresponding α-glycosyl thiols, which could be of great utility in thioglycoside chemistry. It is noteworthy that 1,6-anhydrosugars carrying the 2-O-acyl group and 1,6-anhydrosugar-containing oligosaccharides could also be ring-opened stereospecifically under the same conditions to give rise to the corresponding 1-thiosugars in high yields. Thus, a very concise and efficient access to α-glycosyl thiols of great value was established (Figure presented).
α-Glucosidase Inhibitors, 6. - Synthesis of 1,6-Anhydro-D-glucose and -D-galactose Derivatives - Preparation of 1-Deoxynojirimycin
Schmidt, Richard R.,Michel, Josef,Ruecker, Ernst
, p. 423 - 428 (2007/10/02)
Methyl 2,3-di-O-benzyl-D-glucopyranoside (2) is transformed in the presence of p-toluenesulfonic acid and 2,2,2-trichloro- or 2,2,2-trifluoroethanol into the 4-O-unprotected 1,6-anhydropyranose 4.The amount of 1,6-anhydrofuranose 5, formed as a byproduct of this reaction, can be increased by longer reaction times.Similarly, from methyl 2,3-di-O-benzyl-D-galactopyranoside (9) the corresponding 1,6-anhydro compounds 10 and 12 were obtained. 1-Deoxynojirimycin (31) is obtained from the 5-O-unprotected 1,6-anhydroglucofuranose 5 in a few steps.The stereoselectiveintroduction of nitrogen at C-5 is reached by inversion of the configuration of the 5-OH group through oxidation and reduction and subsequent triflate activation for the invertive azide group introduction
