benzyl 6-O-p-toluene-sulfonyl-α-D-glucopyranoside | 114219-24-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl 6-O-p-toluene-sulfonyl-α-D-glucopyranoside
• 英文别名: [(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-phenylmethoxyoxan-2-yl]methyl 4-methylbenzenesulfonate
• CAS: 114219-24-8
• 化学式: C₂₀H₂₄O₈S
• 分子量: 424.472
• InChiKey: UGKRVULERSDYKA-OBKDMQGPSA-N

物化性质

• 沸点：
  626.0±55.0 °C(predicted)
• 密度：
  1.44±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  131
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  benzyl 6-O-p-toluene-sulfonyl-α-D-glucopyranoside 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 生成 benzyl 6-deoxy-α-D-glucopyranoside
  参考文献：
  名称：

  On the regioselectivity of the protease subtilisin towards the acylation of enantiomeric pairs of benzyl and naphthyl glycopyranosides. Part 2

  摘要：

  Subtilisin-catalyzed esterification of several enantiomeric benzyl and naphthyl glycopyranosides has been investigated. The D-sugar derivatives were all good substrates and subtilisin regioselectivity was similar with all the compounds tested, the 3-OH being acylated predominantly. On the other hand, most of the L-glycopyranosides were transformed during longer reaction times with a lower regioselectivity, the 2-OH being preferentially but not exclusively acylated. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)01217-4
• 作为产物：
  描述：

  a-无水葡萄糖酯 在 吡啶 、 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 生成 benzyl 6-O-p-toluene-sulfonyl-α-D-glucopyranoside
  参考文献：
  名称：

  非对映选择性Passerini反应合成糖代谢药

  摘要：

  我们描述了在Passerini反应中与各种酸和异氰化物一起使用双异亚丙基保护的d-果糖衍生的醛的利用。以高收率和非对映选择性获得了一个载有多达3个碳水化合物单元的高密度功能化拟糖物文库。确定了新形成的立体中心的构型，并通过DFT计算合理化了非对映选择性。

  DOI：

  10.1021/acs.joc.8b01874

文献信息

• Partially Benzylated Derivatives of 6-Deoxy-D-glucose
  作者：Shinkiti Koto、Naohiko Morishima、Yoko Mori、Hitoshi Tanaka、Seiichi Hayashi、Yumi Iwai、Shonosuke Zen

  DOI：10.1246/bcsj.60.2301

  日期：1987.6

  Several partially benzylated derivatives of 6-deoxy-d-glucose (d-quinovose) were synthesized from appropriate di-O-benzyl-d-glucosides whose primary hydroxyl group is unprotected, via unimolar tosylation and subsequent reduction with LiAlH4.

  通过单摩尔数量的甲苯磺酰化反应和随后的LiAlH4还原反应，从适当的二-O-苄基-d-葡糖苷（其伯羟基未保护）合成了6-脱氧-d-葡萄糖（d-黄花草糖）的几种部分苄基化衍生物。
• The effect of heteroatom substitution of sulfur for selenium in glucosidase inhibitors on intestinal α-glucosidase activities
  作者：Razieh Eskandari、Kyra Jones、David R. Rose、B. Mario Pinto

  DOI：10.1039/c1cc13052h

  日期：——

  The synthesis of selenium analogues of de-O-sulfonated ponkoranol, a naturally occurring sulfonium-ion glucosidase inhibitor isolated from Salacia reticulata, and their evaluation as glucosidase inhibitors against two recombinant intestinal enzymes maltase glucoamylase (MGAM) and sucrase isomaltase (SI) are described.

  本文描述了天然发生的磺酸阳离子糖苷酶抑制剂去-O-磺酸化的 ponkoranol 的硒类似物的合成，以及它们作为糖苷酶抑制剂对两种重组肠道酶——麦芽糖酶-葡萄糖淀粉酶（MGAM）和蔗糖-异麦芽糖酶（SI）的评估。
• Potent Glucosidase Inhibitors: De-<i>O</i>-sulfonated Ponkoranol and Its Stereoisomer
  作者：Razieh Eskandari、Douglas A. Kuntz、David R. Rose、B. Mario Pinto

  DOI：10.1021/ol1004005

  日期：2010.4.2

  Ponkoranol, a glucosidase inhibitor isolated from the plant Salacia reticulata, comprises a sulfonium ion with an internal sulfate counterion. An efficient synthetic route to de-O-sulfonated ponkoranol and its 5'-stereoisomer is reported, and it is shown that these compounds are potent glucosidase inhibitors that inhibit a key intestinal human glucosidase, the N-terminal catalytic domain of maltase glucoamylase, with K, values of 43 +/- 3 and 15 +/- 1 nM, respectively.