2,5-anhydro-6-azido-3,4-di-O-benzyl-6-deoxy-D-glucitol | 171973-88-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,5-anhydro-6-azido-3,4-di-O-benzyl-6-deoxy-D-glucitol
• 英文别名: 2,5-anhydro-1-azido-3,4-di-O-benzyl-1-deoxy-D-glucitol；[(2S,3R,4R,5R)-5-(azidomethyl)-3,4-bis(phenylmethoxy)oxolan-2-yl]methanol
• CAS: 171973-88-9
• 化学式: C₂₀H₂₃N₃O₄
• 分子量: 369.42
• InChiKey: CLMVOWGJGPFBFJ-IYWMVGAKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  62.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,5-anhydro-6-azido-3,4-di-O-benzyl-6-deoxy-D-glucitol 在 钯 咪唑 、 四丁基氟化铵 、 氢气 作用下， 以 四氢呋喃 、 甲醇 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 218.0h， 生成 N-[6'-(2',5'-anhydro-3',4'-di-O-benzyl-6'-deoxy-D-glucitol)]-3,4-di-O-benzyl-1,5-dideoxy-1,5-imino-L-gulitol
  参考文献：
  名称：

  假二（或三）糖的合成及其糖苷酶抑制活性

  摘要：

  伪二（或三）糖类与d-mannoazepane或1- gulopiperidine骨架任一合成Ñ -连接到D-葡糖- Ç其抑制活性的-furanoside或d甘露醇，和评价对描述了α-或β-d-葡糖苷酶，α-d-甘露糖苷酶和α-1-岩藻糖苷酶。

  DOI：

  10.1016/s0040-4020(03)00257-6
• 作为产物：
  描述：

  3,4-di-O-benzyl-D-mannitol 在 咪唑 、 氯化亚砜 、 sodium azide 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 16.5h， 生成 2,5-anhydro-6-azido-3,4-di-O-benzyl-6-deoxy-D-glucitol
  参考文献：
  名称：

  Synthesis of α,ω‐Diazidoalditol Derivatives via Both bis‐ or tris‐Cyclic Sulfites and Peracetylated α,ω‐Dibromoalditols as Bielectrophilic Intermediates

  摘要：

  The alpha,omega-diazidoalditol derivatives with erythro, threo, xylo, ribo, D-arabino, D-manno, and D-gluco configuration were efficiently synthesized, respectively, from bis- or tris-cyclic sulfite or peracetylated alpha,omega-dibromoalditol intermediates. The cyclic sulfite intermediates has the advantage to lead directly to the free alpha,omega-diazido-alpha,omega-dideoxyalditols.

  DOI：

  10.1081/car-120030470

文献信息

• Synthesis and conformational studies of 3,4-di-O-acylated furanoid sugar amino acid-containing analogs of the receptor binding inhibitor of vasoactive intestinal peptide
  作者：T.K. Chakraborty、S. Uday Kumar、B. Krishna Mohan、G. Dattatreya Sarma、M. Udaya Kiran、B. Jagadeesh

  DOI：10.1016/j.tetlet.2007.07.158

  日期：2007.9

  Structural analysis of the di-O-caprylated Gaa-containing analog of the receptor binding inhibitors of vasoactive intestinal peptide by various NMR techniques and constrained molecular dynamics (XID) simulation studies established a well-defined beta-turn structure in DMSO-d(6) with an intramolecular hydrogen bond between TyrNH -> MetCO. (c) 2007 Elsevier Ltd. All rights reserved.
• Carbohydrate mimics: analogues of aza-di-(or tri-)saccharides
  作者：Yves Le Merrer、Michèle Sanière、Isabelle McCort、Catherine Dupuy、Jean-Claude Depezay

  DOI：10.1016/s0040-4039(01)00242-8

  日期：2001.4

  Four enantiopure pseudo-aza-di-(or tri-)saccharides have been synthesized by aminocyclization of a C-2-symmetrical D-manno-bis-epoxide either with a primary amine having a polyhydroxylated tetrahydrofuran skeleton or with a polyhydroxylated piperidine or azepan. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Synthesis of sugar-like amino-carboxylic acids from D-mannitol
  作者：L Poitout

  DOI：10.1016/00404-0399(50)14024-

  日期：1995.9.18

  6-Amino-25-anhydro-6-deoxy-D-gluconic and L-gulonic acid derivatives, conformationally restricted sugar-like amino-carboxylic acids which mimic dipeptides, have been synthesized by a silica gel assisted azidolysis of enantiomaically pure bis-epoxides.
• Synthesis of α,ω‐Diazidoalditol Derivatives via Both <i>bis</i>‐ or <i>tris</i>‐Cyclic Sulfites and Peracetylated α,ω‐Dibromoalditols as Bielectrophilic Intermediates
  作者：Virginie Glaçon、Mohammed Benazza、Aniss El Anzi、Daniel Beaupère、Gilles Demailly

  DOI：10.1081/car-120030470

  日期：2004.12.26

  The alpha,omega-diazidoalditol derivatives with erythro, threo, xylo, ribo, D-arabino, D-manno, and D-gluco configuration were efficiently synthesized, respectively, from bis- or tris-cyclic sulfite or peracetylated alpha,omega-dibromoalditol intermediates. The cyclic sulfite intermediates has the advantage to lead directly to the free alpha,omega-diazido-alpha,omega-dideoxyalditols.
• Synthesis and glycosidase inhibitory activity of pseudo-di-(or tri-)saccharides
  作者：Isabelle McCort、Michèle Sanière、Yves Le Merrer

  DOI：10.1016/s0040-4020(03)00257-6

  日期：2003.4

  The synthesis of pseudo-di-(or tri-)saccharides with a d-mannoazepane or a l-gulopiperidine skeleton either N-linked to a d-gluco-C-furanoside or to d-mannitol, and evaluation of their inhibitory activities against α- or β-d-glucosidase, α-d-mannosidase and α-l-fucosidase are described.

  伪二（或三）糖类与d-mannoazepane或1- gulopiperidine骨架任一合成Ñ -连接到D-葡糖- Ç其抑制活性的-furanoside或d甘露醇，和评价对描述了α-或β-d-葡糖苷酶，α-d-甘露糖苷酶和α-1-岩藻糖苷酶。