(2S,3R,4S,5S,6R)-2-(((2R,3R,4S,5R,6R)-4-acetoxy-2-(acetoxymethyl)-6-azido-5-iodotetrahydro-2H-pyran-3-yl)oxy)-6-(acetoxymethyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate | 1391835-74-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3R,4S,5S,6R)-2-(((2R,3R,4S,5R,6R)-4-acetoxy-2-(acetoxymethyl)-6-azido-5-iodotetrahydro-2H-pyran-3-yl)oxy)-6-(acetoxymethyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate
• CAS: 1391835-74-7
• 化学式: C₂₄H₃₂IN₃O₁₅
• 分子量: 729.434
• InChiKey: JJSJEKOFZKAJKL-KOHAQWJGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.79
• 重原子数：
  43.0
• 可旋转键数：
  11.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  234.25
• 氢给体数：
  0.0
• 氢受体数：
  16.0

反应信息

• 作为产物：
  描述：

  2,2',3,3',4',6,6'-七-O-乙酰基-alpha-D-乳糖基溴化物 在 sodium azide 、 一氯化碘 、 溶剂黄146 、 锌 作用下， 以 水 、 乙腈 为溶剂， 反应 2.0h， 生成 (2S,3R,4S,5S,6R)-2-(((2R,3R,4S,5R,6R)-4-acetoxy-2-(acetoxymethyl)-6-azido-5-iodotetrahydro-2H-pyran-3-yl)oxy)-6-(acetoxymethyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate
  参考文献：
  名称：

  Synthesis of multivalent N-acetyl lactosamine modified quantum dots for the study of carbohydrate and galectin-3 interactions

  摘要：

  Ternary core/shell CdSeS/ZnS-QDs coated with N-acetyl lactosamine was prepared as a fluorescent probe to study the interactions of N-acetyl lactosamine and galectin-3. The synthesis of N-acetyl lactosamine was achieved through the 'azidoiodoglycosylation' method. The amount of ligand coated on QDs was determined by H-1 NMR and ICP-OES. The interactions between carbohydrates and galectin-3 were measured using SPR. The results revealed that the affinity of galectin-3 with di- and multivalent N-acetyl lactosamine increased 20 and 184-fold, respectively. The prepared glyco-QDs could be used as an efficient fluorescent probe to study carbohydrates and galectin-3 interactions. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.06.035

文献信息

• Sulfonium Salts of Iodine(I) Species as Efficient Reagents for the Regioselective Bisfunctionalisation of ­Glycals and Enol Ethers
  作者：Thurpu Raghavender Reddy、Dodla Sivanageswara Rao、Kalvacherla Babachary、Sudhir Kashyap

  DOI：10.1002/ejoc.201501183

  日期：2016.1

  A new sulfonium-salt-based iodine(I) reagent system for the vicinal functionalisation of glycals and enol ethers has been developed. The unprecedented iodine(I) complex, Me3SI(OAc)2, generated in situ from Me3SI and PhI(OAc)2, effectively promoted the one-pot iodocarboxylation using carboxylic acids, and iodoazidation using NaN3 or TMSN3 (trimethylsilyl azide). The scope and generality of the new reagent

  已经开发了一种新的基于锍盐的碘 (I) 试剂系统，用于糖类和烯醇醚的邻位功能化。由 Me3SI 和 PhI(OAc)2 原位生成的前所未有的碘 (I) 络合物 Me3SI(OAc)2，有效地促进了使用羧酸的一锅碘羧化反应，以及使用 NaN3 或 TMSN3（叠氮化三甲基甲硅烷基）的碘化叠氮化反应。探索了新试剂的范围和通用性，适用于各种底物，包括各种取代的芳香族羧酸、杂环、脂环族和脂肪族羧酸和氨基酸，以高产率 (99 %) 获得各种功能化的糖缀合物非对映选择性高达 100%。
• Stereoselective Conversion of Dihydropyran and Glycals to 1-Azido-2-halo Derivatives Using NIS/NBS-TMSN₃
  作者：Syed Khalid Yousuf、Altaf Hussain、Deepak Kumar Sharma、Abdul Haleem Wani、Baldev Singh、Debaraj Mukherjee、Subhash C. Taneja

  DOI：10.1080/07328303.2011.590259

  日期：2011.2.1

  Dihydropyran and glycals are readily converted to the corresponding trans-2-deoxy-2-haloazide derivatives in excellent yields within a few minutes using NIS/NBS-TMSN3 at rt in the absence of any catalyst. The use of stoichiometric amounts of the reagents under mild experimental conditions together with the simplicity of the reaction protocol is the notable feature of this transformation.