A mild and efficient method for the selective cleavage of primary p-methoxybenzyl protecting group of saccharides by Co2(CO)8–Me2PhSiH–CO system

Qian, Peng-zhan; Yao, Wang; Huang, Lu-bai; Meng, Xiangbao; Li, Zhongjun

doi:10.1016/j.tetlet.2015.07.051

Cited by 6 publications

(2 citation statements)

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“…Compounds 2 – 4 were then deprotected with 80% acetic acid/H2normalO solution to give the corresponding diol analogs 5 – 7 [35,42]. Reduction of 1 , 3 , and 4 by BH 3 /THF and trimethylsilyl trifluoromethanesulfonate (TMSOTf) [44], and reduction of 2 by diisobutylaluminium hydride (DIBAL-H) [45] resulted in the formation of the 6-OH derivatives 8 – 11 [35,46,47]. Moreover, compounds 1 – 4 were treated with triethylsilane and trifluoroacetic acid (TFA) [48] to afford the 4-OH derivatives 12 – 15 [35,49].…”

Section: Resultsmentioning

confidence: 99%

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Synthesis and Comparative Structure–Activity Study of Carbohydrate-Based Phenolic Compounds as α-Glucosidase Inhibitors and Antioxidants

et al. 2019

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Twenty-one natural and unnatural phenolic compounds containing a carbohydrate moiety were synthesized and their structure–activity relationship (SAR) was evaluated for α-glucosidase inhibition and antioxidative activity. Varying the position of the galloyl unit on the 1,5-anhydro-d-glucitol (1,5-AG) core resulted in changes in the α-glucosidase inhibitory activity and notably, particularly strong activity was demonstrated when the galloyl unit was present at the C-2 position. Furthermore, increasing the number of the galloyl units significantly affected the α-glucosidase inhibition, and 2,3,4,6-tetra-galloyl-1,5-AG (54) and 2,3,4,6-tetra-galloyl-d-glucopyranose (61) exhibited excellent activities, which were more than 13-fold higher than the α-glucosidase inhibitory activity of acertannin (37). Moreover, a comparative structure-activity study suggested that a hemiacetal hydroxyl functionality in the carbohydrate core and a biaryl bond of the 4,6-O-hexahydroxydiphenoyl (HHDP) group, which are components of ellagitannins including tellimagrandin I, are not necessary for the α-glucosidase inhibitory activity. Lastly, the antioxidant activity increased proportionally with the number of galloyl units.

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Section: Resultsmentioning

confidence: 99%

“…3,4-Di-O-benzyl-1,5-anhydro - d- glucitol ( 10 ) [47]; Compound 4 (850 g, 2.5 mmol) in 15 mL of DCM was successively added 12.5 mL of borane-THF (ca. 1M THF solution) and TMSOTf (90 μL, 0.5 mmol) at 0 °C.…”

Section: Methodsmentioning

confidence: 99%