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

中文名称
——
中文别名
——
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
benzyl 6-O-p-toluene-sulfonyl-α-D-glucopyranoside化学式
CAS
114219-24-8
化学式
C20H24O8S
mdl
——
分子量
424.472
InChiKey
UGKRVULERSDYKA-OBKDMQGPSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

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

上下游信息

  • 上游原料
    中文名称 英文名称 CAS号 化学式 分子量
  • 下游产品
    中文名称 英文名称 CAS号 化学式 分子量

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:
    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
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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.
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