acetyl 3,4-di-O-acetyl-6-deoxy-2-deoxy-2-iodo-α-D-mannopyranoside | 381727-48-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: acetyl 3,4-di-O-acetyl-6-deoxy-2-deoxy-2-iodo-α-D-mannopyranoside
• 英文别名: acetyl 3,4-di-O-acetyl-2,6-dideoxy-2-iodo-α-D-mannohexopyranose；[(2R,3R,4S,5S,6R)-4,6-diacetyloxy-5-iodo-2-methyloxan-3-yl] acetate
• CAS: 381727-48-6
• 化学式: C₁₂H₁₇IO₇
• 分子量: 400.167
• InChiKey: AVTYAEFYCIXPRO-BKPRMLKUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  88.1
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  acetyl 3,4-di-O-acetyl-6-deoxy-2-deoxy-2-iodo-α-D-mannopyranoside 在 Amberlyst A-26 (OH^- form) 、 polystyrene-bound silyl triflate 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 25.0h， 生成 testosteryl 2,6-dideoxy-2-iodo-α-D-manno-hexopyranoside
  参考文献：
  名称：

  The First Polymer-Assisted Solution-Phase Synthesis of Deoxyglycosides

  摘要：

  [GRAPHICS]A glycosylation protocol for the synthesis of 2-deoxyglycosides has been developed which is based on the use of polymer-bound reagents. Glycals are transformed into 2-iodoglycosyl acetates using polymer-bound bis(acetoxy)iodate(1) complex (1). Activation of the anomeric center is achieved by employing polymer-bound silyl triflate (2). In the presence of different glycosyl acceptors, 2-deoxy-2-iodoglycosides are generated in very good yields. Furthermore, it is shown that this method can be embedded in multistep sequences toward glycosylated testosterone and rhodinosyl-olivosyl-olivoside.

  DOI：

  10.1021/ol016545v
• 作为产物：
  描述：

  、 3,4-di-O-acetyl-D-rhamnal 在 溶剂黄146 作用下， 反应 0.17h， 以56%的产率得到
  参考文献：
  名称：

  碘 (I) 种类的锍盐作为用于乙二醇和烯醇醚区域选择性双功能化的有效试剂

  摘要：

  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%。

  DOI：

  10.1002/ejoc.201501183

文献信息

• Copper mediated iodoacetoxylation and glycosylation: effective and convenient approaches for the stereoselective synthesis of 2-deoxy-2-iodo glycosides
  作者：Suresh Kumar Battina、Sudhir Kashyap

  DOI：10.1016/j.tetlet.2016.01.035

  日期：2016.2

  Copper(II) triflate catalyzed stereoselective glycosylation of 2-iodo-glycosyl acetate donor is reported. Anomeric activation of 2-deoxy-1-O-acetyl sugar employing Cu(OTf)2 found to be an attractive as well effective alternative reagent to the most frequently used triflic acid (TfOH) source such as TMSOTf or TBSOTf. Scope of the reaction was explored for various aglycones. This protocol involves simple

  报道了三氟甲磺酸铜（II）催化2-碘-糖基乙酸乙酸酯供体的立体选择性糖基化。发现使用Cu（OTf）2的2-脱氧-1- O-乙酰基糖的端基活化是最常用的三氟甲磺酸（TfOH）来源（如TMSOTf或TBSOTf）的诱人且有效的替代试剂。探索了各种糖苷配基的反应范围。该方案涉及简单的反应操作，采用较便宜且无毒的试剂系统，并且能够立体选择性地制备2-脱氧-2-碘-糖苷。此外，CuI / NaIO 4在环境温度下在AcOH的存在下促进了各种糖类的区域选择性碘乙酰氧基化，从而获得了2-碘-糖基乙酸酯。
• Stereoselective Synthesis of Functionalized Precursors of the CDEF and CDE 2,6-Dideoxy-tetra- and Trisaccharide Units of Durhamycins A and B
  作者：Timothy B. Durham、William R. Roush

  DOI：10.1021/ol034395d

  日期：2003.5.1

  [structure: see text] Highly stereoselective syntheses of functionalized precursors of the CDEF and CDE 2,6-dideoxy-tetra- and trisaccharide units of the anti-HIV aureolic acids durhamycins A and B using 2-deoxy-2-iodo- and 2-deoxy-2-bromopyranosyl donors are described.

  [结构：见正文]使用2-deoxy-2-iodo-和2的抗HIV金抗酸Durhamycins A和B的CDEF和CDE的功能化前体的2,6-二脱氧-四-和三糖单元的功能化前体的高度立体选择性合成描述了-脱氧-2-溴吡喃糖基供体。