(3R)-hydroxy-(4S,5S)-bis-benzyloxy-(6R)-benzyloxymethyl-(2S)-phenyl-2-oxo-2λ5-[1,2]oxaphosphinane | 1096144-07-8

• 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: (3R)-hydroxy-(4S,5S)-bis-benzyloxy-(6R)-benzyloxymethyl-(2S)-phenyl-2-oxo-2λ5-[1,2]oxaphosphinane
• 英文别名: (Sp,R,S,S,R)-3-hydroxy-4,5-bis-benzyloxy-6-benzyloxymethyl-2-phenyl-2-oxo-2λ5-[1,2]oxaphosphinane；4,5-bis-benzyloxy-6-benzyloxymethyl-2-phenyl-2-oxo-2λ5-[1,2]oxaphosphinan-3-ol；(2S,3R,4S,5S,6R)-2-oxo-2-phenyl-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)-1,2lambda5-oxaphosphinan-3-ol；(2S,3R,4S,5S,6R)-2-oxo-2-phenyl-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)-1,2λ5-oxaphosphinan-3-ol
• CAS: 1096144-07-8
• 化学式: C₃₂H₃₃O₆P
• 分子量: 544.584
• InChiKey: BFDNKVJGHOSKET-IIXSRDTASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  39
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (3R)-hydroxy-(4S,5S)-bis-benzyloxy-(6R)-benzyloxymethyl-(2S)-phenyl-2-oxo-2λ5-[1,2]oxaphosphinane 在 二乙胺基三氟化硫 作用下， 以 二氯甲烷 为溶剂， 以2.7%的产率得到(2S_p,3S,4S,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-fluoro-2-phenyl-2-oxo-2λ⁵-[1,2]-oxaphosphinane
  参考文献：
  名称：

  α-Halogenated oxaphosphinanes: Synthesis, unexpected reactions and evaluation as inhibitors of cancer cell proliferation

  摘要：

  This paper describes the preparation and the biological evaluation of a-halogenated oxaphosphinanes. These halogen derivatives were synthetized from a short and stereoselective synthetic sequence starting by previously described hydroxy-precursors 1 and 2 with respectively a glucose and mannose-like configuration. The in vitro biological tests of these unnatural halogenated phosphinosugars, on several cell lines, highlighted, for some of them, their antiproliferative and anti migration and invasion properties at nanomolar concentration. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.09.027
• 作为产物：
  描述：

  2,3,5-三-O-(苯基甲基)-D-呋喃阿拉伯糖 、 ethyl Phenylphosphinate 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 生成 (3S)-hydroxy-(4S,5S)-bis-benzyloxy-(6R)-benzyloxymethyl-(2S)-phenyl-2-oxo-2λ5-[1,2]oxaphosphinane 、 (3R)-hydroxy-(4S,5S)-bis-benzyloxy-(6R)-benzyloxymethyl-(2S)-phenyl-2-oxo-2λ5-[1,2]oxaphosphinane 、 (3S)-hydroxy-(4S,5S)-bis-benzyloxy-(6R)-benzyloxymethyl-(2R)-phenyl-2-oxo-2λ5-[1,2]oxaphosphinane 、 (3R)-hydroxy-(4S,5S)-bis-benzyloxy-(6R)-benzyloxymethyl-(2R)-phenyl-2-oxo-(2λ5)-[1,2]oxaphosphinane
  参考文献：
  名称：

  [EN] CRYSTALLINE POLYMORPHIC FORM OF 3-HYDROXY-4,5-BIS-BENZYLOXY-6-BENZYLOXYMETHYL-2-PHENYL-2-OXO-2LAMBDA5-[1,2]OXAPHOSPHINANE
  [FR] FORME POLYMORPHE CRISTALLINE DE 3-HYDROXY-4,5-BIS-BENZYLOXY-6-BENZYLOXYMÉTHYL-2-PHÉNYL-2-OXO -2 LAMBDA5-[1,2]OXYPHOSPHINANE

  摘要：

  本发明涉及一种新的晶态多形形式的3-羟基-4,5-双苄氧基-6-苄氧甲基-2-苯基-2-氧代-2λ5-[1,2]氧磷杂环戊烷及其制备方法。

  公开号：

  WO2018054925A1

文献信息

• Synthesis of Oxaphosphinane-Based Pseudodisaccharides
  作者：Rachida Babouri、Ludovic Clarion、Marc Rolland、Arie Van der Lee、Zahia Kabouche、Jean-Noël Volle、David Virieux、Jean-Luc Pirat

  DOI：10.1002/ejoc.201700878

  日期：2017.10.2

  The synthesis of pseudodisaccharides based on an oxaphosphinane heterocycle is described. Disaccharide mimetics 5 and 6 were readily obtained through glycosylation of a hydroxy group with appropriately protected furanosyl or pyranosyl carbohydrates using a trichloroacetamidate coupling strategy. Selective or complete deprotection then produced the chiral pseudodisaccharides in good yields.

  描述了基于氧杂膦杂环的假二糖的合成。使用三氯乙酰胺酸酯偶联策略，通过羟基与适当保护的呋喃糖基或吡喃糖基碳水化合物进行糖基化，很容易获得二糖模拟物 5 和 6。选择性或完全脱保护然后以良好的产率产生手性假二糖。
• [EN] CRYSTALLINE POLYMORPHIC FORM OF 3-HYDROXY-4,5-BIS-BENZYLOXY-6-BENZYLOXYMETHYL-2-PHENYL-2-OXO-2LAMBDA5-[1,2]OXAPHOSPHINANE<br/>[FR] FORME POLYMORPHE CRISTALLINE DE 3-HYDROXY-4,5-BIS-BENZYLOXY-6-BENZYLOXYMÉTHYL-2-PHÉNYL-2-OXO -2 LAMBDA5-[1,2]OXYPHOSPHINANE
  申请人：PHOSTIN

  公开号：WO2018054925A1

  公开（公告）日：2018-03-29

  The present invention relates to a novel crystalline polymorphic form of 3-Hydroxy- 4,5-bis-benzyloxy-6-benzyloxymethyl-2-phenyl-2-oxo-2λ5-[1,2]oxaphosphinane and a method for preparing the same.

  本发明涉及一种新的晶态多形形式的3-羟基-4,5-双苄氧基-6-苄氧甲基-2-苯基-2-氧代-2λ5-[1,2]氧磷杂环戊烷及其制备方法。
• Crystalline polymorphic form of 3-hydroxy-4,5-bis-benzyloxy-6-benzyloxymethyl-2-phenyl-2-OXO-2λ5-[1,2]oxaphosphinane
  申请人：PHOST'IN

  公开号：US10597414B2

  公开（公告）日：2020-03-24

  The present invention relates to a novel crystalline polymorphic form of 3-Hydroxy-4,5-bis-benzyloxy-6-benzyloxymethyl-2-phenyl-2-oxo-2λ5-[1,2]oxaphosphinane and a method for preparing the same.

  本发明涉及 3-羟基-4,5-双苄氧基-6-苄氧基甲基-2-苯基-2-氧代-2λ5-[1,2]氧磷烷的一种新型结晶多晶型和制备方法。
• CRYSTALLINE POLYMORPHIC FORM OF 3-HYDROXY-4,5-BIS-BENZYLOXY-6-BENZYLOXYMETHYL-2-PHENYL-2-0X0-2LAMBDA5-[l ,2]0XAPHOSPHINANE
  申请人：PHOST'IN

  公开号：US20190330252A1

  公开（公告）日：2019-10-31

  The present invention relates to a novel crystalline polymorphic form of 3-Hydroxy-4,5-bis-benzyloxy-6-benzyloxymethyl-2-phenyl-2-oxo-2λ5-[1,2]oxaphosphinane and a method for preparing the same.
• Oxaphosphinanes: New Therapeutic Perspectives for Glioblastoma
  作者：Ludovic Clarion、Carine Jacquard、Odile Sainte-Catherine、Séverine Loiseau、Damien Filippini、Marie-Hélène Hirlemann、Jean-Noël Volle、David Virieux、Marc Lecouvey、Jean-Luc Pirat、Norbert Bakalara

  DOI：10.1021/jm201428a

  日期：2012.3.8

  This paper reports the design and the synthesis of a new family of compounds, the phostines, belonging to the [1,2]oxaphosphinane family. Twenty-six compounds have been screened for their antiproliferative activity against a large panel of NCI cancer cell lines. Because of its easy synthesis and low EC50 value (500 nM against the C6 rat glioma cell line); compound 3.1a was selected for further biological study. Moreover, the specific biological effect of 3.1a on the glioblastoma phylogenetic cluster from the NCI is dependent on its stereochemistry. Within that cluster, 3.1a has a higher antiproliferative activity than Temozolomide and is more potent than paclitaxel for the SF295 and SNB75 cell lines. In constrast with paclitaxel and vincristine, 3.1a is devoid of astrocyte toxicity. The original activity spectrum of 3.1a on the NCI cancer cell line panel allows the development of this family for use in association with existing drugs, opening new therapeutic perspectives.