4-benzyloxy-1,1,1-trimethoxybutane | 205865-93-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-benzyloxy-1,1,1-trimethoxybutane
• 英文别名: Benzene, [(4,4,4-trimethoxybutoxy)methyl]-；4,4,4-trimethoxybutoxymethylbenzene
• CAS: 205865-93-6
• 化学式: C₁₄H₂₂O₄
• 分子量: 254.326
• InChiKey: YWTDDTHULBMHAN-UHFFFAOYSA-N

物化性质

• 沸点：
  325.1±42.0 °C(Predicted)
• 密度：
  1.030±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  18
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-benzyloxy-1,1,1-trimethoxybutane 在 palladium dihydroxide 三(2-氯乙基)胺 、 氢气 、 丙酸 、 间氯过氧苯甲酸 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 乙酸乙酯 、 甲苯 、 苯 为溶剂， 反应 2.0h， 生成 (3aR,7S,9R,9aR,9bS)-7-(2-Benzyloxy-ethyl)-9-hydroxy-2,2-dimethyl-hexahydro-[1,3]dioxolo[4,5-a]indolizin-6-one
  参考文献：
  名称：

  Synthesis and mannosidase inhibitory activity of 6- and 7-substituted analogs of swainsonine

  摘要：

  Swainsonine (1), an inhibitor of the important glycoprotein-processing enzyme Golgi alpha -mannosidase II, is a clinical candidate for cancer treatment. Analogs bearing substituents at C-6 and C-7 have been prepared and evaluated as inhibitors of alpha -mannosidase (jack bean), a closely related enzyme. (C) 2001 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(01)01778-6

文献信息

• A Novel One-Pot Procedure for the Stereoselective Synthesis of α-Hydroxy Esters from Ortho Esters
  作者：Matthias Breuning、Tobias Häuser、Eva-Maria Tanzer

  DOI：10.1021/ol901214n

  日期：2009.9.17

  A novel one-pot procedure for the stereoselective synthesis of α-hydroxy esters from ortho esters was developed. Key steps were multi-heteroatom Cope rearrangements of O-acylated N-hydroxy-l-tert-leucinol-derived oxazoline N-oxides leading to α-acyloxy oxazolines and, after methanolysis, to the target molecules in 67−80% yield and 94−98% ee.

  开发了一种新颖的一锅法，用于从原酸酯立体选择性地合成α-羟基酯。关键步骤是多的杂原子的柯普重排ö -acylated Ñ羟基升-叔-leucinol衍生恶唑啉Ñ -oxides导致α酰氧基恶唑啉和，甲醇分解之后，到目标分子在67-80％的产率和94 −98％ee。
• NOVEL 6 OR 7 SUBSTITUTED ANALOGUES OF SWAINSONINE, PROCESSES FOR THEIR PREPARATION AND THEIR USE AS THERAPEUTIC AGENTS
  申请人：Glycodesign Inc.

  公开号：EP0934317A2

  公开（公告）日：1999-08-11
• US6630484B1
  申请人：——

  公开号：US6630484B1

  公开（公告）日：2003-10-07
• [EN] NOVEL 6 OR 7 SUBSTITUTED ANALOGUES OF SWAINSONINE, PROCESSES FOR THEIR PREPARATION AND THEIR USE AS THERAPEUTIC AGENTS<br/>[FR] NOUVEAUX ANALOGUES DE SWAINSONINE SUBSTITUES EN POSITION 6 OU 7, LEURS PROCEDES DE PREPARATION ET LEUR UTILISATION COMME AGENTS THERAPEUTIQUES
  申请人：——

  公开号：WO1998014445A2

  公开（公告）日：1998-04-09

  [EN] The invention relates to 6 or 7 substituted swainsonine analogues, processes for their preparation and their use as therapeutic agents. The invention also relates to pharmaceutical compositions containing the compounds and their use as therapeutics.
  [FR] L'invention concerne des analogues de la swainsonine substitués en position 6 ou 7, leurs procédés de préparation et leur utilisation comme agents thérapeutiques. Elle concerne également des compositions pharmaceutiques contenant ces composés et leurs utilisation comme agents thérapeutiques.
• Synthesis and mannosidase inhibitory activity of 6- and 7-substituted analogs of swainsonine
  作者：William H Pearson、Erik J Hembre

  DOI：10.1016/s0040-4039(01)01778-6

  日期：2001.11

  Swainsonine (1), an inhibitor of the important glycoprotein-processing enzyme Golgi alpha -mannosidase II, is a clinical candidate for cancer treatment. Analogs bearing substituents at C-6 and C-7 have been prepared and evaluated as inhibitors of alpha -mannosidase (jack bean), a closely related enzyme. (C) 2001 Published by Elsevier Science Ltd.