(5S,7R,8R,9S,10R)-8,9,10-tribenzyloxy-7-benzyloxymethyl-1-tert-butoxycarbonyl-3,6-dioxa-2-thia-1-azaspiro[4.5]decane-2,2-dioxide | 1192412-18-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (5S,7R,8R,9S,10R)-8,9,10-tribenzyloxy-7-benzyloxymethyl-1-tert-butoxycarbonyl-3,6-dioxa-2-thia-1-azaspiro[4.5]decane-2,2-dioxide
• 英文别名: tert-butyl (5S,7R,8R,9S,10R)-2,2-dioxo-8,9,10-tris(phenylmethoxy)-7-(phenylmethoxymethyl)-3,6-dioxa-2lambda6-thia-1-azaspiro[4.5]decane-1-carboxylate；tert-butyl (5S,7R,8R,9S,10R)-2,2-dioxo-8,9,10-tris(phenylmethoxy)-7-(phenylmethoxymethyl)-3,6-dioxa-2λ6-thia-1-azaspiro[4.5]decane-1-carboxylate
• CAS: 1192412-18-2
• 化学式: C₄₀H₄₅NO₁₀S
• 分子量: 731.864
• InChiKey: XMYIINKUJIJOAU-OORFJYBMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  52
• 可旋转键数：
  15
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  127
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (5S,7R,8R,9S,10R)-8,9,10-tribenzyloxy-7-benzyloxymethyl-1-tert-butoxycarbonyl-3,6-dioxa-2-thia-1-azaspiro[4.5]decane-2,2-dioxide 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以100%的产率得到(5S,7R,8R,9S,10R)-8,9,10-tribenzyloxy-7-benzyloxymethyl-3,6-dioxa-2-thia-1-azaspiro[4.5]decane-2,2-dioxide
  参考文献：
  名称：

  Regioselective synthesis and biological evaluation of spiro-sulfamidate glycosides from exo-glycals

  摘要：

  We report the synthesis of spiro-sulfamidate glycosides from exo-glycals. This route is regioselective and furnishes an original class of spiro-hydantoin glycoside analogues. A biological evaluation of this family on a range of glycosidases shows that these compounds are weak but very selective inhibitors of a-glucosidase and amyloglucosidase. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.07.012
• 作为产物：
  描述：

  3,4,5,7-tetra-O-benzyl-α-D-gluco-hept-2-ulopyranose 、 tert-butyl (N-triethylammonium sulfonyl)carbamate 以 四氢呋喃 为溶剂， 反应 4.0h， 以73%的产率得到(5S,7R,8R,9S,10R)-8,9,10-tribenzyloxy-7-benzyloxymethyl-1-tert-butoxycarbonyl-3,6-dioxa-2-thia-1-azaspiro[4.5]decane-2,2-dioxide
  参考文献：
  名称：

  Regioselective synthesis and biological evaluation of spiro-sulfamidate glycosides from exo-glycals

  摘要：

  We report the synthesis of spiro-sulfamidate glycosides from exo-glycals. This route is regioselective and furnishes an original class of spiro-hydantoin glycoside analogues. A biological evaluation of this family on a range of glycosidases shows that these compounds are weak but very selective inhibitors of a-glucosidase and amyloglucosidase. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.07.012