5-(benzyloxy)-1,3,2-dioxathiane 2,2-dioxide | 874620-22-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-(benzyloxy)-1,3,2-dioxathiane 2,2-dioxide
• 英文别名: 5-Phenylmethoxy-1,3,2-dioxathiane 2,2-dioxide
• CAS: 874620-22-1
• 化学式: C₁₀H₁₂O₅S
• 分子量: 244.268
• InChiKey: ZFNQCAJMQQWNOM-UHFFFAOYSA-N

物化性质

• 沸点：
  378.6±31.0 °C(Predicted)
• 密度：
  1.38±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  70.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-(benzyloxy)-1,3,2-dioxathiane 2,2-dioxide 、 (2R,3S,4S)-2-(hydroxymethyl)tetrahydrothiophene-3,4-diol 在 potassium carbonate 作用下， 以 various solvent(s) 为溶剂， 反应 60.0h， 生成
  参考文献：
  名称：

  Synthesis and biological evaluation of deoxy salacinols, the role of polar substituents in the side chain on the α-glucosidase inhibitory activity

  摘要：

  Three analogs (5, 6, and 7) lacking polar substituents in the side chain of a naturally occurring a-glucosidase inhibitor, salacinol (la), were synthesized by the coupling reaction of a thiosugar, 1,4-dideoxy-1,4-epithio-D-arabinitol (3), with cyclic sulfates (8, 9, and 10), and their a-glucosidase inhibitory activities were examined. All these simpler analogs (5, 6, and 7) showed less inhibitory activity compared to la, and proved the importance of cooperative role of the polar substituents for the a-glucosidase inhibitory activity. A practical synthetic route to 3 starting from D-xylose is also described. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.08.040
• 作为产物：
  描述：

  2-苄氧基-1,3-丙二醇 在 ruthenium trichloride 、 sodium periodate 、 氯化亚砜 、 碳酸氢钠 、 三乙胺 作用下， 以 四氯化碳 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 0.67h， 生成 5-(benzyloxy)-1,3,2-dioxathiane 2,2-dioxide
  参考文献：
  名称：

  Synthesis and biological evaluation of deoxy salacinols, the role of polar substituents in the side chain on the α-glucosidase inhibitory activity

  摘要：

  Three analogs (5, 6, and 7) lacking polar substituents in the side chain of a naturally occurring a-glucosidase inhibitor, salacinol (la), were synthesized by the coupling reaction of a thiosugar, 1,4-dideoxy-1,4-epithio-D-arabinitol (3), with cyclic sulfates (8, 9, and 10), and their a-glucosidase inhibitory activities were examined. All these simpler analogs (5, 6, and 7) showed less inhibitory activity compared to la, and proved the importance of cooperative role of the polar substituents for the a-glucosidase inhibitory activity. A practical synthetic route to 3 starting from D-xylose is also described. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.08.040

文献信息

• Nickel-Catalyzed Asymmetric Kumada Cross-Coupling of Symmetric Cyclic Sulfates
  作者：Meredith S. Eno、Alexander Lu、James P. Morken

  DOI：10.1021/jacs.6b03384

  日期：2016.6.29

  Nickel-catalyzed enantioselective cross-couplings between symmetric cyclic sulfates and aromatic Grignard reagents are described. These reactions are effective with a broad range of substituted cyclic sulfates and deliver products with asymmetric tertiary carbon centers. Mechanistic experiments point to a stereoinvertive SN2-like oxidative addition of a nickel complex to the electrophilic substrate

  描述了对称环状硫酸盐和芳香格氏试剂之间的镍催化的对映选择性交叉偶联。这些反应对广泛的取代环硫酸盐有效，并提供具有不对称叔碳中心的产物。机理实验表明，镍络合物在亲电子底物上发生了立体反转的 SN2 样氧化加成反应。
• Isolation, structure identification and SAR studies on thiosugar sulfonium salts, neosalaprinol and neoponkoranol, as potent α-glucosidase inhibitors
  作者：Weijia Xie、Genzoh Tanabe、Junji Akaki、Toshio Morikawa、Kiyofumi Ninomiya、Toshie Minematsu、Masayuki Yoshikawa、Xiaoming Wu、Osamu Muraoka

  DOI：10.1016/j.bmc.2011.01.052

  日期：2011.3

  Two hitherto missing members of sulfonium salts family in Salacia genus plants as a new class of a-glucosidase inhibitors, neoponkoranol (7) and neosalaprinol (8), were isolated from the water extracts, and their structures were unambiguously identified. For further SAR studies on this series of sulfonium salts, several epimers of 7 and 8 were synthesized, and their inhibitory activities against rat small intestinal alpha-glucosidases were evaluated. Among them, 3'-epimer of 7 was found most potent in this class of molecules, and revealed as potent as currently used antidiabetics, voglibose and acarbose. (C) 2011 Elsevier Ltd. All rights reserved.
• Synthesis and elucidation of absolute stereochemistry of salaprinol, another thiosugar sulfonium sulfate from the ayurvedic traditional medicine Salacia prinoides
  作者：Genzoh Tanabe、Mika Sakano、Toshie Minematsu、Hisashi Matusda、Masayuki Yoshikawa、Osamu Muraoka

  DOI：10.1016/j.tet.2008.08.010

  日期：2008.10

  Synthesis and elucidation of absolute stereochemistry of salaprinol (3) isolated from the root and sterns of Salacia prinoides, which has been used for the treatment of diabetes in India, Sri Lanka, and Southeast Asia countries, is described. Compound 3 and its 2'-epimer, epi-salaprinol (epi-3) were synthesized via the coupling reaction of a cyclic sulfate, 2-O-benzylglycerol 1,3-cyclic sulfate (S), with a thiosugar, 1,4-dideoxy-1,4-epithio-D-arabinitol (6), as the key reaction, and S configuration of the asymmetric center in the side chain of 3 was elucidated by the X-ray crystallographic analysis. (C) 2008 Published by Elsevier Ltd.
• Synthesis and biological evaluation of deoxy salacinols, the role of polar substituents in the side chain on the α-glucosidase inhibitory activity
  作者：Osamu Muraoka、Kazuya Yoshikai、Hideo Takahashi、Toshie Minematsu、Guangxin Lu、Genzoh Tanabe、Tao Wang、Hisashi Matsuda、Masayuki Yoshikawa

  DOI：10.1016/j.bmc.2005.08.040

  日期：2006.1

  Three analogs (5, 6, and 7) lacking polar substituents in the side chain of a naturally occurring a-glucosidase inhibitor, salacinol (la), were synthesized by the coupling reaction of a thiosugar, 1,4-dideoxy-1,4-epithio-D-arabinitol (3), with cyclic sulfates (8, 9, and 10), and their a-glucosidase inhibitory activities were examined. All these simpler analogs (5, 6, and 7) showed less inhibitory activity compared to la, and proved the importance of cooperative role of the polar substituents for the a-glucosidase inhibitory activity. A practical synthetic route to 3 starting from D-xylose is also described. (c) 2005 Elsevier Ltd. All rights reserved.