Methyl-2.3-O-isopropyliden-β-L-gulofuranosid | 50692-26-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Methyl-2.3-O-isopropyliden-β-L-gulofuranosid
• 英文别名: (1S)-1-[(3aS,4S,6R,6aS)-4-methoxy-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]ethane-1,2-diol
• CAS: 50692-26-7
• 化学式: C₁₀H₁₈O₆
• 分子量: 234.249
• InChiKey: IKOWBTZQUCUCHP-BGKGJTHRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  77.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Methyl-2.3-O-isopropyliden-β-L-gulofuranosid 在 吡啶 、 4 A molecular sieve 、 二正丁基氧化锡 作用下， 以 苯 为溶剂， 反应 31.0h， 生成 methyl 6-O-benzyl-2,3-O-isopropylidene-5-O-methanesulfonyl-β-L-gulofuranoside
  参考文献：
  名称：

  双环二氮杂糖。第3部分：β-d-甘露糖和6-脱氧-β-1-古洛糖类似物

  摘要：

  β-d-甘露吡喃糖的双环类似物，其中氮原子取代了环和糖苷氧原子，是通过5 - O-甲磺酰基-d-甘露糖呋喃糖通过一步法制备的，该过程可能涉及两次置换和环氧化物中间体。已经通过亲电环化反应制备了类似但受保护的6-脱氧-β-1-戊吡喃糖的双环类似物。

  DOI：

  10.1016/s0040-4020(01)01011-0
• 作为产物：
  描述：

  methyl 2,3:5,6-di-O-isopropylidene-Β-L-gulofuranoside 在 甲醇 作用下， 反应 0.5h， 以89%的产率得到Methyl-2.3-O-isopropyliden-β-L-gulofuranosid
  参考文献：
  名称：

  Ultrasound-Assisted Selective Deprotection of Terminal Acetonides Catalyzed by Silica-Supported Boron Trifluoride

  摘要：

  An efficient and convenient method for the selective cleavage of terminal acetonides is described. Treatment of terminal acetonides in the presence of a wide range of functional groups with silica-supported boron trifluoride as a catalyst furnished the corresponding diols in 8295% yield under ultrasound irradiation conditions. The acid-labile p-methoxybenzyl group as a protecting group remained intact under the conditions employed to the present deprotection condition.

  DOI：

  10.1080/07328303.2012.762980

文献信息

• Ultrasound-Assisted Selective Deprotection of Terminal Acetonides Catalyzed by Silica-Supported Boron Trifluoride
  作者：Junlong Xiong、Shiqiang Yan、Ning Ding、Wei Zhang、Yingxia Li

  DOI：10.1080/07328303.2012.762980

  日期：2013.3.24

  An efficient and convenient method for the selective cleavage of terminal acetonides is described. Treatment of terminal acetonides in the presence of a wide range of functional groups with silica-supported boron trifluoride as a catalyst furnished the corresponding diols in 8295% yield under ultrasound irradiation conditions. The acid-labile p-methoxybenzyl group as a protecting group remained intact under the conditions employed to the present deprotection condition.
• Bicyclic diazasugars. Part 3: β-d-Mannose and 6-deoxy-β-l-gulose analogues
  作者：David A Berges、Jianmei Fan、Nannan Liu、N Kent Dalley

  DOI：10.1016/s0040-4020(01)01011-0

  日期：2001.12

  nitrogen atoms replacing the ring and glycosidic oxygen atoms has been prepared in a single step from 5-O-mesyl-d-mannofuranose by a process that likely involves double displacement and an epoxide intermediate. A similar but protected bicyclic analogue of 6-deoxy-β-l-gulopyranose has been prepared by an electrophilic cyclization reaction.

  β-d-甘露吡喃糖的双环类似物，其中氮原子取代了环和糖苷氧原子，是通过5 - O-甲磺酰基-d-甘露糖呋喃糖通过一步法制备的，该过程可能涉及两次置换和环氧化物中间体。已经通过亲电环化反应制备了类似但受保护的6-脱氧-β-1-戊吡喃糖的双环类似物。