3,5-C-dimethyl-3,5,6,7,8-pentadeoxy-1,2-O-isopropylidene-β-L-talo-octofuranose | 918165-22-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,5-C-dimethyl-3,5,6,7,8-pentadeoxy-1,2-O-isopropylidene-β-L-talo-octofuranose
• 英文别名: (3aR,5R,6R,6aR)-2,2,6-trimethyl-5-[(2S)-pentan-2-yl]-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole
• CAS: 918165-22-7
• 化学式: C₁₃H₂₄O₃
• 分子量: 228.332
• InChiKey: URPCPZJTWSNJGM-VSSNEEPJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 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：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3,5-C-dimethyl-3,5,6,7,8-pentadeoxy-1,2-O-isopropylidene-β-L-talo-octofuranose 在 吡啶 、 2,6-二甲基吡啶 、 盐酸 、 dimethyl sulfide borane 、 水 、 戴斯-马丁氧化剂 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 10.5h， 生成 (2E,4E,7S,8S,9R,10S)-9-(tert-butyl-dimethyl-silanyloxy)-7-methoxy-8,10-dimethyl-trideca-2,4-dienoic acid methyl ester
  参考文献：
  名称：

  Stereoselective synthesis of the polyketide chain of nagahamide A

  摘要：

  A carbohydrate based approach for the enantioselective synthesis of the polyketide acid unit present in nagahamide A has been reported. Reductive ring opening of a chiral cyclopropane ketone group to enantioselectively install the methyl and propyl groups, is a salient feature of this synthesis. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.09.025
• 作为产物：
  描述：

  O-[(4S)-4-[(3aR,5R,6R,6aR)-2,2,6-trimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]pentan-2-yl] methylsulfanylmethanethioate 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 甲苯 为溶剂， 反应 3.0h， 以73%的产率得到3,5-C-dimethyl-3,5,6,7,8-pentadeoxy-1,2-O-isopropylidene-β-L-talo-octofuranose
  参考文献：
  名称：

  Stereoselective synthesis of the polyketide chain of nagahamide A

  摘要：

  A carbohydrate based approach for the enantioselective synthesis of the polyketide acid unit present in nagahamide A has been reported. Reductive ring opening of a chiral cyclopropane ketone group to enantioselectively install the methyl and propyl groups, is a salient feature of this synthesis. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.09.025

文献信息

• OLIGOMERIC COMPOUNDS COMPRISING ALPHA-BETA-CONSTRAINED NUCLEIC ACID
  申请人：IONIS PHARMACEUTICALS, INC.

  公开号：US20170044539A1

  公开（公告）日：2017-02-16

  The present disclosure provides oligomeric compounds comprising at least one α-β-constrained nucleic acid as provided herein. More particularly, the α-β-constrained nucleic acid provided herein comprise an optionally modified nucleoside with a phosphorus containing constrained internucleoside linkage such as for example a cyclic phosphate internucleoside linkage. The α-β-constrained nucleic acid provided herein are expected to be useful for enhancing one or more properties of oligomeric compounds they are incorporated into such as for example nuclease resistance. In certain embodiments, the oligomeric compounds provided herein hybridize to a portion of a target RNA resulting in loss of normal function of the target RNA.
• Stereoselective synthesis of the polyketide chain of nagahamide A
  作者：Debendra K. Mohapatra、Siddhartha Ray Chaudhuri、Gokarneswar Sahoo、Mukund K. Gurjar

  DOI：10.1016/j.tetasy.2006.09.025

  日期：2006.10

  A carbohydrate based approach for the enantioselective synthesis of the polyketide acid unit present in nagahamide A has been reported. Reductive ring opening of a chiral cyclopropane ketone group to enantioselectively install the methyl and propyl groups, is a salient feature of this synthesis. (c) 2006 Elsevier Ltd. All rights reserved.