METHYL 2,3,4-TRI-O-BENZYL-6-DEOXY-α-D-GLUCOHEPTOPYRANOSIDE | 133918-92-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: METHYL 2,3,4-TRI-O-BENZYL-6-DEOXY-α-D-GLUCOHEPTOPYRANOSIDE
• 英文别名: methyl 2,3,4-tri-O-benzyl-6-deoxy-alpha-D-glucoheptopyranoside；2-[(2R,3R,4S,5R,6S)-6-methoxy-3,4,5-tris(phenylmethoxy)oxan-2-yl]ethanol
• CAS: 133918-92-0
• 化学式: C₂₉H₃₄O₆
• 分子量: 478.585
• InChiKey: IMIUUOMKTPBICJ-RQKPWJHBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  35
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  66.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  METHYL 2,3,4-TRI-O-BENZYL-6-DEOXY-α-D-GLUCOHEPTOPYRANOSIDE 在 N-碘代丁二酰亚胺 作用下， 以 硝基甲烷 为溶剂， 以84%的产率得到(5aR,7S,8R,9S,9aR)-7-methoxy-2-phenyl-8,9-bis(phenylmethoxy)-5,5a,7,8,9,9a-hexahydro-4H-pyrano[3,2-d][1,3]dioxepine
  参考文献：
  名称：

  A New Intramolecular Reaction for the Regioselective Debenzylation or Protection of Alcohols

  摘要：

  DOI：

  10.1002/(sici)1521-3773(19981204)37:22<3177::aid-anie3177>3.3.co;2-1
• 作为产物：
  描述：

  methyl 6-aldehydo-2,3,4-tri-O-benzyl-α-D-glucopyranoside 在 sodium hydroxide 、 正丁基锂 、 dimethyl sulfide borane 、 双氧水 作用下， 生成 METHYL 2,3,4-TRI-O-BENZYL-6-DEOXY-α-D-GLUCOHEPTOPYRANOSIDE
  参考文献：
  名称：

  具有酸不稳定保护基的糖基氯的合成

  摘要：

  在碱性条件下，由其相应的醇以良好的收率制备了具有酸不稳定保护基的糖基氯。在二碘化sa（II）存在下，通过糖基氯与醛的反应进行1，6-C-连接的二糖的合成。

  DOI：

  10.1016/0040-4039(96)01006-4

文献信息

• Novel alpha-glucosidase inhibitors
  申请人：MERRELL DOW PHARMACEUTICALS INC.

  公开号：EP0389723A1

  公开（公告）日：1990-10-03

  This invention relates to novel N-derivatives, of 1,4-di-­deoxy-1,4-imino-L-arabinitol (I), to the processes for their preparation and to their end-use applications, particularly as to their use in the treatment of diabetes. wherein n is zero, one or two, and R is a glycosyl or etherified or acylated glycosyl radical containing from 1 to 3 hexose or pentose units, said glycosyl radical optionally bearing an ether or ester derivative of the hydroxyl moiety located on the anomeric carbon atom.

  本发明涉及新颖的1,4-二脱氧-1,4-亚氨基-L-阿拉伯糖醇（I）的N-衍生物，涉及其制备方法及其最终用途，特别是作为治疗糖尿病的用途。 其中n为0、1或2，R为含有1至3个己糖或戊糖单元的糖基或醚化或酰化的糖基基团，所述糖基基团任选地在其异头碳原子上的羟基部分带有醚或酯衍生物。
• A New Method for the Deprotection of Benzyl Ethers or the Selective Protection of Alcohols
  作者：Jacob Madsen、Christel Viuf、Mikael Bols

  DOI：10.1002/(sici)1521-3765(20000403)6:7<1140::aid-chem1140>3.3.co;2-y

  日期：2000.4.3

  A new selective method for the deprotection of benzyl ethers situated next to alcohols in the alpha, beta, or gamma position is presented which uses either NIS or DIB/I2 as a reagent. After initial formation of a hypoiodite intermediate, the reaction is believed to follow a radical pathway to resemble the Hoffman-Loffler-Freytag reaction. The formation of the intermediate hypoiodite is suggested on

  提出了一种新的选择性方法，该方法使用NIS或DIB / I2作为试剂，对位于α，β或gamma位置的醇旁边的苄基醚进行脱保护。最初形成次碘酸盐中间体后，该反应被认为遵循自由基途径，类似于霍夫曼-洛夫勒-弗莱塔格反应。在NMR研究的基础上，建议形成中间的次碘酸盐。取决于底物，分离出相应的亚苄基衍生物或二醇。
• .alpha.-glucosidase inhibitors
  申请人：Merrell Dow Pharmaceuticals Inc.

  公开号：US05097023A1

  公开（公告）日：1992-03-17

  This invention relates to novel N-glycosyl derivatives of 1,4-dideoxy-1,4-imino-D-arabinitol, to the chemical processes for their preparation, to their .alpha.-glucosidase inhibiting properties, and to their end-use application in the treatment of diabetes, obesity and those diseases associated with retroviruses, particularly the HIV virus reported to be the causative of the acquired immune deficiency syndrome (AIDS).

  本发明涉及1,4-二脱氧-1,4-亚氨基-D-阿拉伯糖醇的新型N-糖基衍生物、其制备的化学过程、其α-葡萄糖苷酶抑制性能以及其在治疗糖尿病、肥胖症和与逆转录病毒相关的疾病中的应用，尤其是被认为是获得性免疫缺陷综合症（艾滋病）病因的HIV病毒的治疗应用。
• Novel alpha-Glucosidase inhibitors
  申请人：MERRELL DOW PHARMACEUTICALS INC.

  公开号：EP0344383A1

  公开（公告）日：1989-12-06

  This invention relates to novel N-derivatives of 1-deoxy-nojirimyoin, to the processes for their preparation and to their end-use applications, particularly as to their use in the treatment of diabetes.

  本发明涉及 1-脱氧野尻yoin的新型 N-衍生物、其制备工艺及其最终用途，特别是在治疗糖尿病方面的应用。
• Novel Alpha-glucosidase inhibitors
  申请人：MERRELL DOW PHARMACEUTICALS INC.

  公开号：EP0345104A2

  公开（公告）日：1989-12-06

  This invention relates to novel N-derivatives of 1-deoxy-nojirimycin (1) to the processes for their preparation and to their end-use applications, particularly as to their use in the treatment of diabetes. wherein n is zero, one or two, and R is a glycosyl or etherified or acylated glycosyl radical containing from 1 to 3 hexose or pentose units, said glycosyl radical optionally bearing an ether or ester derivative of the hydroxyl moeity located on the anomeric carbon atom of the terminal hexose or pentose moeity.

  本发明涉及 1-脱氧-野尻霉素（1）的新型 N 衍生物及其制备工艺和最终应用，特别是在糖尿病治疗中的应用。 其中 n 为 0、1 或 2，R 为含有 1 至 3 个己糖或戊糖单元的糖基或醚化或酰化的糖基，所述糖基任选带有位于末端己糖或戊糖单元的异构碳原子上的羟基的醚或酯衍生物。