(3aR,4R,5R,6S,6aR) 2-[5-(2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-yloxy]ethanol | 34819-96-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3aR,4R,5R,6S,6aR) 2-[5-(2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-yloxy]ethanol
• 英文别名: 3-O-(2-hydroxyethyl)-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose；3-O-hydroxyethyl-1,2:5,6-di-O-isopropylidene-α-D-glucopyranose；2-[[(3aR,5R,6S,6aR)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-yl]oxy]ethanol
• CAS: 34819-96-0
• 化学式: C₁₄H₂₄O₇
• 分子量: 304.34
• InChiKey: OOKVMRLOOHQNNF-RMPHRYRLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  75.6
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (3aR,4R,5R,6S,6aR) 2-[5-(2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-yloxy]ethanol 在 溶剂黄146 作用下， 以 水 为溶剂， 反应 12.0h， 以78%的产率得到(1R,3aR,5R,6S,6aR) 1-[6-(2-hydroxyethoxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl]ethan-1,2-diol
  参考文献：
  名称：

  Bicyclic nucleoside analogues from d-glucose: synthesis of chiral as well as racemic 1,4-dioxepane ring-fused derivatives

  摘要：

  The dioxepanofuranose derivatives 4 and 12, obtained through the cyclization of the 3-(2-hydroxyethyl) ether of a D-xylo-pentodialdose derivative, were appropriately functionalized and elaborated to the first examples of the new class of 3 '-O, and 5 '-O-bicyclic nucleoside analogues 9, 10, and 14 with a fused seven-membered ring. Reactions carried out through the intermediacy of the D-xylo-pentodialdose derivative 5 yielded racemic products, while prior protection of the 4-formyl group (as in 7) before deprotection of the 1,2-hydroxyl groups led to optically active analogues. (c) 2005 Elsevier Ltd All rights reserved.

  DOI：

  10.1016/j.carres.2005.02.007
• 作为产物：
  描述：

  (3aR,4R,5R,6S,6aR) [5-(2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-yloxy]acetic acid methyl ester 在 甲醇 、 sodium tetrahydroborate 作用下， 以 叔丁醇 为溶剂， 反应 1.0h， 以79%的产率得到(3aR,4R,5R,6S,6aR) 2-[5-(2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-yloxy]ethanol
  参考文献：
  名称：

  Bicyclic nucleoside analogues from d-glucose: synthesis of chiral as well as racemic 1,4-dioxepane ring-fused derivatives

  摘要：

  The dioxepanofuranose derivatives 4 and 12, obtained through the cyclization of the 3-(2-hydroxyethyl) ether of a D-xylo-pentodialdose derivative, were appropriately functionalized and elaborated to the first examples of the new class of 3 '-O, and 5 '-O-bicyclic nucleoside analogues 9, 10, and 14 with a fused seven-membered ring. Reactions carried out through the intermediacy of the D-xylo-pentodialdose derivative 5 yielded racemic products, while prior protection of the 4-formyl group (as in 7) before deprotection of the 1,2-hydroxyl groups led to optically active analogues. (c) 2005 Elsevier Ltd All rights reserved.

  DOI：

  10.1016/j.carres.2005.02.007

文献信息

• 一种新型烟用保润剂3-O-羟乙基-D-葡萄糖及 其制备方法
  申请人：河南中烟工业有限责任公司

  公开号：CN103467536B

  公开（公告）日：2016-03-30

  本发明公开了一种新型烟用保润剂3-O-羟乙基-D-葡萄糖，其结构为：，本发明同时公开了该化合物的制备方法，以D-葡萄糖为原料，通过引入异丙叉基对D-葡萄糖羟基进行保护和去保护，成功合成了所述新型多羟基烟用保润剂3-O-羟乙基-D-葡萄糖。通过物理保润性能测试和内在感官质量评价，发现该保润剂对卷烟具有很好的物理保润作用，并且可降低卷烟刺激性和杂气，提高卷烟烟气圆润感和舒适性。
• Exploring the Optimal Site for Modifications of Pyranmycins with the Extended Arm Approach
  作者：Jie Li、Jinhua Wang、Yu Hui、Cheng-Wei Tom Chang

  DOI：10.1021/ol027288c

  日期：2003.2.1

  [GRAPHICS]Continuing from the syntheses and the antibacterial studies of a library of pyranmycins, we further probed the proximity around ring III of pyranmycin by introducing an "extended arm" that has hydroxyethyl or aminoethyl groups at the O-2", O-3", or O-4" positions. The results from the antibacterial studies reveal the optimal structural motif is the attachment of an extended arm with a terminal hydroxyl group at the O-3" position.
• Bicyclic nucleoside analogues from d-glucose: synthesis of chiral as well as racemic 1,4-dioxepane ring-fused derivatives
  作者：Subhankar Tripathi、Joy Krishna Maity、Basudeb Achari、Sukhendu B. Mandal

  DOI：10.1016/j.carres.2005.02.007

  日期：2005.5

  The dioxepanofuranose derivatives 4 and 12, obtained through the cyclization of the 3-(2-hydroxyethyl) ether of a D-xylo-pentodialdose derivative, were appropriately functionalized and elaborated to the first examples of the new class of 3 '-O, and 5 '-O-bicyclic nucleoside analogues 9, 10, and 14 with a fused seven-membered ring. Reactions carried out through the intermediacy of the D-xylo-pentodialdose derivative 5 yielded racemic products, while prior protection of the 4-formyl group (as in 7) before deprotection of the 1,2-hydroxyl groups led to optically active analogues. (c) 2005 Elsevier Ltd All rights reserved.