| 372494-01-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• CAS: 372494-01-4
• 化学式: C₂₆H₂₇N₃O₄S
• 分子量: 477.584
• InChiKey: OOPBQORWNNDRDF-NCORMGPNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.35
• 重原子数：
  34.0
• 可旋转键数：
  10.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  96.68
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  、 氯乙酸酐 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 以74%的产率得到phenyl 2-azido-3,4-di-O-benzyl-6-O-chloroacetyl-2-deoxy-1-thio-α,β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of glycosaminoglycan oligosaccharides. Part 4: Synthesis of aza-l-iduronic acid-containing analogs of heparan sulfate oligosaccharides as heparanase inhibitors

  摘要：

  The synthesis of three azasugar-containing analogs of the disaccharide units of heparan sulfate, which are potential inhibitors of the enzyme heparanase, is reported. Synthetic routes were developed for the preparation of L-ido-nojirimycin type glycosyl acceptors with O-4 free. Glycosylation of these acceptors with an O-6 functionalized 2-azido-2-deoxy-n-glucose thioglycoside donor afforded the a-linked disaccharides in good yields. The advantages of using the 4-nitrobenzenesulfonyl group for the protection of the ring nitrogen of azasugars were demonstrated. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.07.055
• 作为产物：
  描述：

  phenyl 2-azido-6-O-tert-butyldiphenylsilyl-2-deoxy-1-thio-α/β-D-glucopyranoside 在 四丁基氟化铵 、 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成
  参考文献：
  名称：

  [EN] HEXOSE DERIVATIVES, PREPARATION AND USES THEREOF
  [FR] DÉRIVÉS D'HEXOSE, LEUR PRÉPARATION ET UTILISATIONS

  摘要：

  一个化合物的化学式I：或其盐，其中：R1为-OC(H)(X)(CH2)nC(=O)OH；R2为-OH，-N3或-N(H)C(=O)CH3；或R1和R2与它们连接的碳原子一起形成R3为-H，-CH3，-CH2C(=O)OH或-CH2OH；X为-H，-CH3，-CH2OH或CH2C(=O)OH；n为0或1。

  公开号：

  WO2015137838A1

文献信息

• Improvement of the stereoselectivity of the glycosylation reaction with 2-azido-2-deoxy-1-thioglucoside donors
  作者：E.C. Lourenço、M.R. Ventura

  DOI：10.1016/j.carres.2016.03.021

  日期：2016.5

  2-Azido-2-deoxy-1-thioglucoside donors with an electron withdrawing group at position 6 were employed to study the stereoselectivity of the glycosylation reaction with several acceptors, ranging from unhindered small primary alcohols to other sugars and steroids, using NIS/TfOH as promoter. p-Tolyl 2-azido-3,4-di-O-benzyl-6-O-chloroacetyl-2-deoxy-1-thio-α/β-D-glucopyranoside afforded the higher α-selectivity

  使用NIS / TfOH，使用在6位具有吸电子基团的2-叠氮基2-脱氧-1-硫代葡萄糖苷供体来研究糖基化反应与多个受体的立体选择性，这些受体的范围从无阻碍的小型伯醇到其他糖和类固醇作为发起人。对甲苯基2-叠氮基-3,4-二-O-苄基-6-O-氯乙酰基-2-脱氧-1-硫代-α/β-D-吡喃葡萄糖苷具有较高的α-选择性，表明电子更强在O-6处提取酯影响了对1,2-顺式葡糖苷的异头异构体选择性。端基异构体的立体选择性高度依赖于受体。
• Synthesis of a Potential Heparanase Inhibitor
  作者：Shunya Takahashi、Hiroyoshi Kuzuhara

  DOI：10.1246/cl.1994.2119

  日期：1994.11

  Aza-analog of the basic disaccharide unit in heparan sulfate was designed as a potential inhibitor against heparanase produced by solid tumor cells, and synthesized via a coupling reaction of a phenyl 2-azido-1-thio-d-glucopyranoside derivative with a partially protected 1-deoxynojirymycin derived from d-glucose, followed by manipulation such as imino acid formation, O-sulfation.

  基于肝素硫酸盐中基本二糖单元设计了一种氮杂类似物，作为针对实体瘤细胞产生的肝素酶的潜在抑制剂，并通过苯基2-叠氮基-1-硫代-D-吡�糖苷衍生物与部分保护的1-脱氧野尻霉素（来自D-葡萄糖）的偶联反应合成，随后进行亚胺酸形成、O-硫酸化等操作。
• Design and synthesis of a heparanase inhibitor with pseudodisaccharide structure
  作者：Shunya Takahashi、Hiroyoshi Kuzuhara、Motowo Nakajima

  DOI：10.1016/s0040-4020(01)00642-1

  日期：2001.8

  Aza-analogue of the basic disaccharide unit of heparane sulfate was designed as a potent inhibitor against heparanase produced by solid tumors cell, and synthesized via a coupling reaction of phenyl 2-azide-1-thio-D-glucopyranoside derivatives with a partially protected 1-deoxynojirimycin derived from D-glucose. The azapseudodisaccharide inhibited tumor cell heparanase with IC50 value of 58-63 muM. (C) 2001 Elsevier Science Ltd. All rights reserved.