2,5-anhydro-3-deoxy-4-O-methanesulfonyl-6-O-trityl-L-talose ethylene acetal | 798574-41-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 2,5-anhydro-3-deoxy-4-O-methanesulfonyl-6-O-trityl-L-talose ethylene acetal
• 英文别名: [(2S,3S,5R)-5-(1,3-dioxolan-2-yl)-2-(trityloxymethyl)oxolan-3-yl] methanesulfonate
• CAS: 798574-41-1
• 化学式: C₂₈H₃₀O₇S
• 分子量: 510.608
• InChiKey: DIVIXTWTUCMALQ-NXCFDTQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  36
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  88.7
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2,5-anhydro-3-deoxy-4-O-methanesulfonyl-6-O-trityl-L-talose ethylene acetal 在 palladium on activated charcoal sodium azide 、 氢气 作用下， 以 乙醇 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 20.0~85.0 ℃ 、206.85 kPa 条件下， 反应 28.0h， 生成 (2R,3R,5R)-5-[1,3]Dioxolan-2-yl-2-trityloxymethyl-tetrahydro-furan-3-ylamine
  参考文献：
  名称：

  Ring-expanded analogues of natural oxetanocin

  摘要：

  Synthesis of ring-expanded analogs of the natural compound, oxetanocin is described. The starting material for the synthesis of the series, 4-7, was D-glucosamine and introduction of the base moiety was done through the stereochemically appropriate epoxide. For the enantiomeric series, 8-11, the starting material was D-glucose and preparation of the key intermediate involved a rearrangement reaction. The structures of the target molecules were established by NMR, HRMS, optical rotation and UV data. Single-crystal X-ray data confirmed the enantiomeric structural assignments. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.08.087
• 作为产物：
  描述：

  2,5-anhydro-3-deoxy-L-talose ethylene acetal 在 吡啶 、 三乙胺 作用下， 反应 24.5h， 生成 2,5-anhydro-3-deoxy-4-O-methanesulfonyl-6-O-trityl-L-talose ethylene acetal
  参考文献：
  名称：

  RING-EXPANDED ANALOGUES OF NATURAL OXETANOCIN: (+) AND (−) HYDROXYMETHYL ISODIDEOXYADENOSINE

  摘要：

  New enantiomeric isonucleoside analogues related to natural oxetanocin have been synthesized from D-glucosamine and D-glucose. The structures of the target compounds were confirmed 4 NMR, HRMS, UV single crystal X-ray, and optical rotation data. Stability studies with respect to purine nucleoside phosphorylase and adenosine deaminase show that these compounds are not substrates. Antiviral results are discussed.

  DOI：

  10.1081/ncn-200060036

文献信息

• Ring-expanded analogues of natural oxetanocin
  作者：Vasu Nair、Byoung-Kwon Chun、Jean John Vadakkan

  DOI：10.1016/j.tet.2004.08.087

  日期：2004.11

  Synthesis of ring-expanded analogs of the natural compound, oxetanocin is described. The starting material for the synthesis of the series, 4-7, was D-glucosamine and introduction of the base moiety was done through the stereochemically appropriate epoxide. For the enantiomeric series, 8-11, the starting material was D-glucose and preparation of the key intermediate involved a rearrangement reaction. The structures of the target molecules were established by NMR, HRMS, optical rotation and UV data. Single-crystal X-ray data confirmed the enantiomeric structural assignments. (C) 2004 Elsevier Ltd. All rights reserved.
• RING-EXPANDED ANALOGUES OF NATURAL OXETANOCIN: (+) AND (−) HYDROXYMETHYL ISODIDEOXYADENOSINE
  作者：Byoung-Kwon Chun、Jean John Vadakkan、Vasu Nair

  DOI：10.1081/ncn-200060036

  日期：2005.4.1

  New enantiomeric isonucleoside analogues related to natural oxetanocin have been synthesized from D-glucosamine and D-glucose. The structures of the target compounds were confirmed 4 NMR, HRMS, UV single crystal X-ray, and optical rotation data. Stability studies with respect to purine nucleoside phosphorylase and adenosine deaminase show that these compounds are not substrates. Antiviral results are discussed.