6-O-t-butyldimethylsilyl-3,4-O-isopropylidene-1-deoxymannojirimycin | 938065-94-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-O-t-butyldimethylsilyl-3,4-O-isopropylidene-1-deoxymannojirimycin
• 英文别名: (3aR,4R,7R,7aR)-4-[[tert-butyl(dimethyl)silyl]oxymethyl]-2,2-dimethyl-3a,4,5,6,7,7a-hexahydro-[1,3]dioxolo[4,5-c]pyridin-7-ol
• CAS: 938065-94-2
• 化学式: C₁₅H₃₁NO₄Si
• 分子量: 317.501
• InChiKey: RGDSVMLBTUHDLX-FDYHWXHSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.86
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  60
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-O-t-butyldimethylsilyl-3,4-O-isopropylidene-1-deoxymannojirimycin 在 甲醇 、 Dowex 50W-X₈ 作用下， 反应 3.0h， 生成 1-脱氧甘露伊霉素
  参考文献：
  名称：

  Total Synthesis of Polyhydroxylated Piperidine and Pyrrolidine : Expect as Glucosidase Inhibitor

  摘要：

  A new method for preparation of optically active (-)-deoxymannojirimycin (3) and 2R,5S-dihydroxymethyl-3R,4R-dihydroxypyrrolidine (13) based on regioselective epoxide ring opening of 2-tert-butoxycarbonylamino-2-deoxy-3,4-O-isopropylidene-5,6-epoxy-D-glucitol (12) by intramolecular nucleophilic amination has been described.

  DOI：

  10.3987/com-96-7720
• 作为产物：
  描述：

  D-甘露糖-1,4-内酯 在 吡啶 、 ammonium hydroxide 、 sodium tetrahydroborate 、 H⁽¹⁺⁾ resin 、 氢溴酸 、 sodium acetate 、 对甲苯磺酸 作用下， 以 甲醇 、 硝基甲烷 、 水 、 溶剂黄146 为溶剂， 反应 14.08h， 生成 6-O-t-butyldimethylsilyl-3,4-O-isopropylidene-1-deoxymannojirimycin
  参考文献：
  名称：

  Facile syntheses of 1-deoxynojirimycin (DNJ) and 1-deoxymannojirimycin (DMJ)

  摘要：

  1-Deoxynojirimycin (DNJ) and 1-deoxymannojirimycin (DMJ) were synthesized through a concise and practicable pathway. A strategy of using carbohydrate derivatives bearing two leaving groups in the preparation of azasugars by di-N-alkylation of amines was developed. The strategy involved the selective partial protection of dibromo alditols. (c) 2007 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2007.01.110

文献信息

• Total Synthesis of Polyhydroxylated Piperidine and Pyrrolidine : Expect as Glucosidase Inhibitor
  作者：Sang-Gyeong Lee、Sang Gyeong Lee、Yong-Jin Yoon、Sung Chul Shin、Bu Yong Lee、Su-Dong Cho、Sung Kyu Kim、Ji-Hyun Lee

  DOI：10.3987/com-96-7720

  日期：——

  A new method for preparation of optically active (-)-deoxymannojirimycin (3) and 2R,5S-dihydroxymethyl-3R,4R-dihydroxypyrrolidine (13) based on regioselective epoxide ring opening of 2-tert-butoxycarbonylamino-2-deoxy-3,4-O-isopropylidene-5,6-epoxy-D-glucitol (12) by intramolecular nucleophilic amination has been described.
• Facile syntheses of 1-deoxynojirimycin (DNJ) and 1-deoxymannojirimycin (DMJ)
  作者：Xuezheng Song、Rawle I. Hollingsworth

  DOI：10.1016/j.tetlet.2007.01.110

  日期：2007.4

  1-Deoxynojirimycin (DNJ) and 1-deoxymannojirimycin (DMJ) were synthesized through a concise and practicable pathway. A strategy of using carbohydrate derivatives bearing two leaving groups in the preparation of azasugars by di-N-alkylation of amines was developed. The strategy involved the selective partial protection of dibromo alditols. (c) 2007 Published by Elsevier Ltd.