(2S,3R)-2-(2-Benzyloxy-ethyl)-3-(4-methoxy-benzyloxymethyl)-oxirane | 805246-98-4

• 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: (2S,3R)-2-(2-Benzyloxy-ethyl)-3-(4-methoxy-benzyloxymethyl)-oxirane
• 英文别名: (2R,3S)-2-[(4-methoxyphenyl)methoxymethyl]-3-(2-phenylmethoxyethyl)oxirane
• CAS: 805246-98-4
• 化学式: C₂₀H₂₄O₄
• 分子量: 328.408
• InChiKey: CBSOMBASUMFAPR-VQTJNVASSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  24
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  40.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S,3R)-2-(2-Benzyloxy-ethyl)-3-(4-methoxy-benzyloxymethyl)-oxirane 在 2,6-二甲基吡啶 、 盐酸 、 正丁基锂 、 potassium carbonate 作用下， 以 甲醇 、 正己烷 、 二氯甲烷 、 甲苯 为溶剂， 反应 7.0h， 生成 (2S,6S,7S)-6-[(4-methoxyphenyl)methoxymethyl]-9-phenylmethoxynon-4-yne-1,2,7-triol
  参考文献：
  名称：

  INTERMEDIATE OF ERIBULIN AND SYNTHESIS METHOD AND USE THEREOF

  摘要：

  An intermediate compound is prepared and used for the synthesis of halichondrin B, eribulin or an analog thereof, particularly a structural fragment C27-C35 thereof. The starting materials of the synthetic route are readily available, and the optical purity of the starting materials can be ensured, so that the optical purity of the structural fragment C27-C35 in halichondrin B, eribulin or the analog thereof is ensured. Steps for constructing a chiral center of the structural fragment C27-C35 feature higher diastereoselectivity and yield, in particular preparation methods of compounds of formulae (X), (XI), (XVI) and (XV). By-products of partial reactions can be removed only by recrystallization, which results in easy purification and significant reduce in cost.

  公开号：

  US20220204523A1
• 作为产物：
  描述：

  D-(+)-核糖酸-gamma-内酯 在 吡啶 、 咪唑 、 4-二甲氨基吡啶 、 硼烷二甲硫醚络合物 、 D(+)-10-樟脑磺酸 、 四丁基氟化铵 、 4-甲基苯磺酸吡啶 、 三氯化硼 、 potassium carbonate 、 potassium iodide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 11.0h， 生成 (2S,3R)-2-(2-Benzyloxy-ethyl)-3-(4-methoxy-benzyloxymethyl)-oxirane
  参考文献：
  名称：

  INTERMEDIATE OF ERIBULIN AND SYNTHESIS METHOD AND USE THEREOF

  摘要：

  An intermediate compound is prepared and used for the synthesis of halichondrin B, eribulin or an analog thereof, particularly a structural fragment C27-C35 thereof. The starting materials of the synthetic route are readily available, and the optical purity of the starting materials can be ensured, so that the optical purity of the structural fragment C27-C35 in halichondrin B, eribulin or the analog thereof is ensured. Steps for constructing a chiral center of the structural fragment C27-C35 feature higher diastereoselectivity and yield, in particular preparation methods of compounds of formulae (X), (XI), (XVI) and (XV). By-products of partial reactions can be removed only by recrystallization, which results in easy purification and significant reduce in cost.

  公开号：

  US20220204523A1

文献信息

• [EN] INTERMEDIATE OF ERIBULIN, SYNTHESIS METHOD THEREFOR AND USE THEREOF<br/>[FR] INTERMÉDIAIRE D'ÉRIBULINE, SON PROCÉDÉ DE SYNTHÈSE ET SON UTILISATION<br/>[ZH] 艾日布林的中间体及其合成方法和用途
  申请人：BEIJING TIENYI LUFU PHARMATECH CO LTD

  公开号：WO2020216034A1

  公开（公告）日：2020-10-29

  提供可用于合成软海绵素B、艾日布林或其类似物，特别是其C27-C35结构片段的中间体、其制备方法和用途。合成路线的起始原料廉价易得，其光学纯度可以得到保障，从而保证了软海绵素、艾日布林或其类似物中C27-C35结构片段的光学纯度；构建C27-C35结构片段手性中心的步骤方法，具有较高的非对映选择性和产率，尤其是式(X)、式(XI)、式(XVI)和式(XV)所示化合物的制备方法；部分反应的副产物仅需重结晶即可除去，便于纯化，大大降低了成本。
• INTERMEDIATE OF ERIBULIN, SYNTHESIS METHOD THEREFOR AND USE THEREOF
  申请人：Beijing Tienyi Lufu Pharmatech Co. Ltd.

  公开号：EP3925948A1

  公开（公告）日：2021-12-22

  The present invention relates to the field of drug synthesis, and particularly relates to an intermediate of eribulin and a synthesis method and use thereof. The present invention provides an intermediate useful for the synthesis of halichondrin B, eribulin or an analog thereof, particularly a structural fragment C27-C35 thereof, and a preparation method and use thereof. The starting materials of the synthetic route disclosed herein are cheap and easy to obtain, and the optical purity of the starting materials can be ensured, so that the optical purity of the structural fragment C27-C35 in halichondrin B, eribulin or the analog thereof is ensured; steps for constructing a chiral center of the structural fragment C27-C35 feature higher diastereoselectivity and yield, in particular preparation methods of compounds of formulae (X), (XI), (XVI) and (XV); by-products of partial reactions can be removed only by recrystallization, which results in easy purification and significant reduce in cost.

  本发明涉及药物合成领域，尤其涉及一种麦角林的中间体及其合成方法和用途。本发明提供了一种可用于合成卤黄芪 B、麦角林或其类似物，特别是其 C27-C35 结构片段的中间体及其制备方法和用途。本发明所公开的合成路线的起始原料廉价易得，且能保证起始原料的光学纯度，因此能保证卤化龙胆素 B、麦角苷或其类似物中结构片段 C27-C35 的光学纯度；构建结构片段 C27-C35 手性中心的步骤具有更高的非对映选择性和收率，特别是式 (X)、(XI)、(XVI) 和 (XV) 化合物的制备方法；部分反应的副产物只需通过重结晶即可去除，从而易于纯化并显著降低成本。
• Macrocyclic ketone analogues of halichondrin B
  作者：Wanjun Zheng、Boris M. Seletsky、Monica H. Palme、Paul J. Lydon、Lori A. Singer、Charles E. Chase、Charles A. Lemelin、Yongchun Shen、Heather Davis、Lynda Tremblay、Murray J. Towle、Kathleen A. Salvato、Bruce F. Wels、Kimberley K. Aalfs、Yoshito Kishi、Bruce A. Littlefield、Melvin J. Yu

  DOI：10.1016/j.bmcl.2004.08.069

  日期：2004.11

  Structurally simplified macrocyclic ketone analogues of halichondrin B were prepared by total synthesis and found to retain the potent cell growth inhibitory activity in vitro, stability in mouse serum, and in vivo efficacy of the natural product. (C) 2004 Elsevier Ltd. All rights reserved.