N-(2,2-diethoxycarbonylvinyl)-β-D-galactopyranosylamine | 22435-65-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-(2,2-diethoxycarbonylvinyl)-β-D-galactopyranosylamine
• 英文别名: diethyl 2-[[[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]amino]methylidene]propanedioate
• CAS: 22435-65-0
• 化学式: C₁₄H₂₃NO₉
• 分子量: 349.338
• InChiKey: XUYUHPVSRYKWPB-YBXAARCKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  155
• 氢给体数：
  5
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  N-(2,2-diethoxycarbonylvinyl)-β-D-galactopyranosylamine 在 吡啶 、 sodium methylate 、 氯 、 sodium cyanoborohydride 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 、 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 50.0 ℃ 、2.67 kPa 条件下， 反应 100.58h， 生成 (3R,4S,5R,6S)-3,4,5,6-tetrahydroxyazepine
  参考文献：
  名称：

  An easy route to seven-membered iminocyclitols from aldohexopyranosyl enamines

  摘要：

  A new stereocontrolled and high yielding synthesis of biologically active polyhydroxyperhydroazelpines is reported starting from easily available glycosylenamines (D-gluco, D-manno, and D-galacto configurations), which are transformed into 1,6-azaanhydropyranose derivatives. O- and N-Deprotection of the latter, followed by reduction with sodium cyanoborohydride, gives the target chiral iminocyclitols. The method is based on the capacity of the dialkoxycarbonylvinyl group to stabilize an amide ion, and the only limitation is the necessity for the starting glycosylenamine to have beta-D-configuration. The inhibitory activity of several intermediate iminocyclitols and aldopyranosylenamines on different alpha- and beta-glycosidases is also reported. (C) 2002 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(02)00377-4

文献信息

• [EN] COORDINATION COMPOUNDS, SYNTHESES, NANOFORMULATION AND USE THEREOF IN ONCOLOGY<br/>[FR] COMPOSÉS DE COORDINATION, SYNTHÈSES, NANOFORMULATION ET LEUR UTILISATION EN ONCOLOGIE
  申请人：NARDON CHIARA

  公开号：WO2018100562A1

  公开（公告）日：2018-06-07

  The present invention relates to mononuclear and dinuclear coordination compounds of Ru and Ga, pharmaceutical formulations based thereof, the relative method of synthesis and encapsulation of the compounds in macromolecules, supramolecular aggregates or nanostructures, as well as their use for the diagnosis and/or treatment of neoplasia. Advantageously, such coordination compounds and/or formulations may contain carbohydrates which act as "cancer-targeting moieties" thereby increasing therapeutic selectivity. Said compounds and formulations are characterized by a promising toxicological profile, a remarkable and highly-selective anti-cancer activity, as well as stability and solubility in the physiological means.

  本发明涉及钌和镓的一核和二核配位化合物，基于此类配位化合物的药物配方，合成和将化合物封装在大分子、超分子聚集体或纳米结构中的相对方法，以及它们用于诊断和/或治疗肿瘤的用途。优点是，这种配位化合物和/或配方可能含有作为“癌症靶向基团”的碳水化合物，从而增加治疗的选择性。所述化合物和配方具有有前途的毒理学特性，显著且高度选择性的抗癌活性，以及在生理介质中的稳定性和溶解性。
• Regioselective benzoylations of glycopyranosylamines: Synthesis of partially protected glycopyranosyl isothiocyanates
  作者：José Fuentes Mota、José Manuel Garcia Fernandez、Carmen Ortiz Mellet、María Angeles Pradera Adrian、Reyes Babiano Caballero

  DOI：10.1016/0008-6215(89)84056-x

  日期：1989.6

  Abstract Regioselective benzoylations of N -(2,2-diethoxycarbonylvinyl)-β- d -galactopyranosylamine ( 1 ) yielded 2,3,6-tri- O - ( 3 ) and 3,6-di- O -benzoyl- N -(2,2-diethoxycarbonylvinyl)-β- d -galactopyranosylamine ( 4 ), whereas, from the β- d - gluco analogue 5 , the 2,3,6-tri- ( 7 ), 3,6-di- ( 8 ), and 2,6-di- O -benzoyl ( 9 ) derivatives were obtained together with the fully esterified compounds

  摘要N-（2,2-二乙氧基羰基乙烯基）-β-d-吡喃半乳糖苷胺（1）的区域选择性苯甲酰化生成2,3,6-tri-O-（3）和3,6-di-O-苯甲酰基-N-（ 2,2-二乙氧基羰基乙烯基）-β-d-吡喃半乳糖胺（4），而在β-d-葡萄糖类似物5中，2,3,6-tri-（7），3,6-di-（8）和2,6-二-O-苯甲酰基（9）衍生物与完全酯化的化合物（2和6）一起获得。用溴处理3，用氯处理7，得到2,3,6-三-O-苯甲酰基-β-d-甘露型核糖胺氢卤化物（分别为10和11），其与硫光气反应生成2,3,6-三-O-苯甲酰基-β-d-吡喃半乳糖异硫氰酸酯（12）和β-d-葡萄糖类似物14。3，
• A new method for the preparation of acylated glycosylamines and their transformations into glycosyl isothiocyanates and N,N′-diglycosylthioureas
  作者：Reyes Babiano Caballero、Jose Fuentes Mota、Juan Antonio Galbis Perez

  DOI：10.1016/s0008-6215(00)90042-9

  日期：1986.10
• An easy route to seven-membered iminocyclitols from aldohexopyranosyl enamines
  作者：José Fuentes、Consolación Gasch、David Olano、M.Ángeles Pradera、Guillermo Repetto、Francisco J. Sayago

  DOI：10.1016/s0957-4166(02)00377-4

  日期：2002.8

  A new stereocontrolled and high yielding synthesis of biologically active polyhydroxyperhydroazelpines is reported starting from easily available glycosylenamines (D-gluco, D-manno, and D-galacto configurations), which are transformed into 1,6-azaanhydropyranose derivatives. O- and N-Deprotection of the latter, followed by reduction with sodium cyanoborohydride, gives the target chiral iminocyclitols. The method is based on the capacity of the dialkoxycarbonylvinyl group to stabilize an amide ion, and the only limitation is the necessity for the starting glycosylenamine to have beta-D-configuration. The inhibitory activity of several intermediate iminocyclitols and aldopyranosylenamines on different alpha- and beta-glycosidases is also reported. (C) 2002 Published by Elsevier Science Ltd.