7-tert-butyldimethylsilyl-5,6-O-isopropylidene-D-glycero-D-galacto-heptitol | 1231714-26-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 7-tert-butyldimethylsilyl-5,6-O-isopropylidene-D-glycero-D-galacto-heptitol
• 英文别名: (1R,2R,3S)-1-[(4S,5R)-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-2,2-dimethyl-1,3-dioxolan-4-yl]butane-1,2,3,4-tetrol
• CAS: 1231714-26-3
• 化学式: C₁₆H₃₄O₇Si
• 分子量: 366.527
• InChiKey: LUOCGIWWHAXWEE-RYMFRWLXSA-N

物化性质

• 熔点：
  80-81 °C
• 沸点：
  494.8±40.0 °C(Predicted)
• 密度：
  1.107±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  109
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  7-tert-butyldimethylsilyl-5,6-O-isopropylidene-D-glycero-D-galacto-heptitol 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 1.5h， 以5.8 mg的产率得到perseitol
  参考文献：
  名称：

  Characteristic alkaline catalyzed degradation of kotalanol, a potent α-glucosidase inhibitor isolated from Ayurvedic traditional medicine Salacia reticulata, leading to anhydroheptitols: another structural proof

  摘要：

  Stereochemical structure of kotalanol (2), a highly potent a-glucosidase inhibitor isolated from an Ayurvedic traditional medicine Salacia reticulata, was proved by alkaline catalyzed degradation of natural kotalanol (2), in which characteristic stereospecific cyclization of the degradative side chain leading to anhydroheptitols (10 and 11) was involved. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.03.072
• 作为产物：
  描述：

  (E)-7-O-tert-butyldimethylsilyl-2,3-dideoxy-5,6-O-isopropylidene-D-arabino-hept-2-enitol 在 四氧化锇 、 水 、 N-甲基吗啉氧化物 作用下， 以 丙酮 为溶剂， 反应 4.0h， 以520 mg的产率得到7-tert-butyldimethylsilyl-5,6-O-isopropylidene-D-glycero-D-galacto-heptitol
  参考文献：
  名称：

  Characteristic alkaline catalyzed degradation of kotalanol, a potent α-glucosidase inhibitor isolated from Ayurvedic traditional medicine Salacia reticulata, leading to anhydroheptitols: another structural proof

  摘要：

  Stereochemical structure of kotalanol (2), a highly potent a-glucosidase inhibitor isolated from an Ayurvedic traditional medicine Salacia reticulata, was proved by alkaline catalyzed degradation of natural kotalanol (2), in which characteristic stereospecific cyclization of the degradative side chain leading to anhydroheptitols (10 and 11) was involved. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.03.072

文献信息

• Practical Route to Neokotalanol and Its Natural Analogues: Sulfonium Sugars with Antidiabetic Activities
  作者：Yuhao Huang、Yunlong Gao、Weigang He、Zihao Wang、Wei Li、Aijun Lin、Jinyi Xu、Genzoh Tanabe、Osamu Muraoka、Xiaoming Wu、Weijia Xie

  DOI：10.1002/anie.201900761

  日期：2019.5.6

  time. The key strategy features a coupling reaction between thiol derivatives and a diiodide counterpart. The newly designed thiol coupling partner presents high chemical stability, while the diiodide partner could be easily obtained with increased overall yields compared with conventional routes. The intermolecular nucleophilic substitution reaction followed by a diastereoselective intramolecular cyclization

  首次报道了一种高效，多样化的方法，用于合成最初从S藜属植物中分离的所有四种脱-O-磺化α型α-葡萄糖苷酶抑制剂。关键策略是硫醇衍生物与二碘化物对应物之间的偶联反应。新设计的硫醇偶合剂具有较高的化学稳定性，而与常规方法相比，二碘化物偶合剂可以轻松获得，总收率更高。分子间亲核取代反应，随后进行非对映选择性分子内环化，提供了目标五元sulf盐结构，该结构以α-方向连接至多羟基化的侧链部分。
• 一种构建环状锍鎓糖的方法及其在neosalacinol等天然产物合成中的应用
  申请人：中国药科大学

  公开号：CN110078704A

  公开（公告）日：2019-08-02

  本发明属于化学合成领域，具体涉及涉及五层龙属植物中提取的天然产物neosalaprinol、neosalacinol、neoponkoranol以及neokotalanol的全合成方法。该方法由商业途径购买的S‑缩水甘油，D‑阿拉伯糖和D‑葡萄糖为原料，经多步反应合成从五层龙属植物中提取的天然产物neosalaprinol、neosalacinol、neoponkoranol以及neokotalanol。
• Characteristic alkaline catalyzed degradation of kotalanol, a potent α-glucosidase inhibitor isolated from Ayurvedic traditional medicine Salacia reticulata, leading to anhydroheptitols: another structural proof
  作者：Osamu Muraoka、Weijia Xie、Satomi Osaki、Ayumi Kagawa、Genzoh Tanabe、Mumen F.A. Amer、Toshie Minematsu、Toshio Morikawa、Masayuki Yoshikawa

  DOI：10.1016/j.tet.2010.03.072

  日期：2010.5

  Stereochemical structure of kotalanol (2), a highly potent a-glucosidase inhibitor isolated from an Ayurvedic traditional medicine Salacia reticulata, was proved by alkaline catalyzed degradation of natural kotalanol (2), in which characteristic stereospecific cyclization of the degradative side chain leading to anhydroheptitols (10 and 11) was involved. (C) 2010 Elsevier Ltd. All rights reserved.