4,6-O-benzylidene-D-glucose

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: 4,6-O-benzylidene-D-glucose
• 英文别名: 4,6-O-benzylidene-D-glucopyranose；4,6-O-Benzylidene-glucopyranose；(2R,4aR,7R,8R,8aS)-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine-6,7,8-triol
• 化学式: C₁₃H₁₆O₆
• 分子量: 268.266
• InChiKey: FOLRUCXBTYDAQK-FJRULOAQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  88.4
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4,6-O-benzylidene-D-glucose 在 palladium 10% on activated carbon 、 甲酸铵 、 1-羟基苯并三唑 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 53.0h， 生成 N-(((2R,4aR,6S,7R,8R,8aS)-7,8-dihydroxy-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-6-yl)methyl)-2-hydroxybenzamide
  参考文献：
  名称：

  Synthesis and α-glucosidase inhibitory activity evaluation of N-substituted aminomethyl-β-d-glucopyranosides

  摘要：

  A series of N-substituted 1-aminomethyl-beta-D-glucopyranoside derivatives was prepared. These novel synthetic compounds were assessed in vitro for inhibitory activity against yeast a-glucosidase and both rat intestinal a-glucosidases maltase and sucrase. Most of the compounds displayed a-glucosidase inhibitory activity, with IC50 values covering the wide range from 2.3 mu M to 2.0 mM. Compounds 19a (IC50 = 2.31 mu M) and 19b (IC50 = 5.6 mu M) were identified as the most potent inhibitors for yeast a-glucosidase, while compounds 16 (IC50 = 7.7 and 15.6 mu M) and 19e (IC50 = 5.1 and 10.4 mu M) were the strongest inhibitors of rat intestinal maltase and sucrase. Analysis of the kinetics of enzyme inhibition indicated that 19e inhibited maltase and sucrase in a competitive manner. The results suggest that the aminomethyl-beta-o-glucopyranoside moiety can mimic the substrates of a-glucosidase in the enzyme catalytic site, leading to competitive enzyme inhibition. Moreover, the nature of the N-substituent has considerable influence on inhibitory potency. (C) 2013 The Authors. Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.06.002
• 作为产物：
  描述：

  2-Nitrobenzyl-2,3,4,6-tetra-O-acetyl-β-D-glucopyranosid 在 甲醇 、 camphor-10-sulfonic acid 、 sodium methylate 作用下， 以 甲醇 、 水 、 乙腈 为溶剂， 反应 0.75h， 生成 4,6-O-benzylidene-D-glucose
  参考文献：
  名称：

  Tiwari, Varsha; Badavath, Vishnu Nayak; Singh, Adesh Kumar, Journal of the Indian Chemical Society, 2020, vol. 97, # 2, p. 227 - 236

  摘要：

  DOI：

文献信息

• Glycosyl Bunte Salts: A Class of Intermediates for Sugar Chemistry
  作者：Yasuhiro Meguro、Masato Noguchi、Gefei Li、Shin-ichiro Shoda

  DOI：10.1021/acs.orglett.7b03400

  日期：2018.1.5

  thiosulfates have been discovered as a new class of synthetic intermediates in sugar chemistry, named “glycosyl Bunte salts” after 19th-century German chemist, Hans Bunte. The synthesis was achieved by direct condensation of unprotected sugars and sodium thiosulfate using a formamidine-type dehydrating agent in water–acetonitrile mixed solvent. The application of glycosyl Bunte salts is demonstrated with transformation

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  作者：Alois Fürstner、Thomas Müller

  DOI：10.1021/ja991361l

  日期：1999.9.1

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  DOI：10.1021/jo971413u

  日期：1997.11.1

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  作者：Shiue-Shien Weng、Kun-Yi Hsieh、Zih-Jian Zeng

  DOI：10.1002/jccs.201600828

  日期：2017.5

  Thioglycosylation of 1‐hydroxyl glycosides catalyzed by in situ‐generated AlI3 from elemental aluminium and molecular iodine has been developed. This method provides an alternative route to access anomeric thioglycosides without the use of hazard Lewis acidic activators or per‐modified activated thiol sources. The major advantages of this dehydrative procedure are environmental friendly, ease of operation

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  DOI：10.1021/jo400562k

  日期：2013.6.7

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