3-deoxy-3-iodo-5-O-carboxymethyl-1,2-O-isopropylidene-α-D-ribofuranose | 136317-52-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-deoxy-3-iodo-5-O-carboxymethyl-1,2-O-isopropylidene-α-D-ribofuranose
• 英文别名: [(3aR,5R,6R,6aS)-6-iodo-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]methyl methyl carbonate
• CAS: 136317-52-7
• 化学式: C₁₀H₁₅IO₆
• 分子量: 358.13
• InChiKey: VZKMIIDIRPFBPJ-WCTZXXKLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  NaCo(dmgH)2py 、 3-deoxy-3-iodo-5-O-carboxymethyl-1,2-O-isopropylidene-α-D-ribofuranose 以 甲醇 、 水 为溶剂， 以51%的产率得到
  参考文献：
  名称：

  Stereoelectronic control of electron transfer in the oxidative addition of [py(dmgH)2CoI]-Na+ to carbohydrate secondary iodides

  摘要：

  The relative rates of oxidative addition of secondary carbohydrate iodides 2, 5, and 7 with [py(dmgH)2Co(I)]-, to form mixtures of diastereomeric alkyl cobaloximes 3 and 8, are consistent with steric inhibition of the electron-transfer step. On the basis of these and previously reported observations, a unified mechanism for oxidative addition is proposed.

  DOI：

  10.1021/om00057a003
• 作为产物：
  描述：

  1,2-O-isopropylidene-5-O-(methoxycarbonyl)-3-O-triflyl-α-D-xylofuranose 在 n-Bu₄I 作用下， 以 苯 为溶剂， 反应 7.0h， 以3.10 g的产率得到3-deoxy-3-iodo-5-O-carboxymethyl-1,2-O-isopropylidene-α-D-ribofuranose
  参考文献：
  名称：

  Thermal and Photochemical Epimerization/Equilibration of Carbohydrate Cobaloximes

  摘要：

  Epimeric carbohydrate alkyl cobaloximes 4:5, 9:10, and 12:13 can be equilibrated thermally or photochemically. In each case, one isomer is strongly favored: exo-3-deoxy-3-pyridyldimethylgly-oximatocobalt-1,2:5,6-di-O-isopropylidene-alpha -D-glucofuranose 4 for the 4:5 epimer pair, exo-3-deoxy-3-pyridyldimethylglyoximatocobalt-5-O-carboxymethyl-1,2-O-isopropylidene-alpha -D-xylofuranose 9 for the 9:10 epimer pair, and equatorial 1-deoxy-1-pyridyldimethylglyoximatocobalt-2,3,4,6-tetra-O-benzyl-beta -D-glucopyranose 12 for the 12:13 epimer pair. These data indicate that there is a strong facial preference for the coupling of py(dmgH)(2)Co-. radicals with alkyl R-. free radicals, with the preferred kinetic path leading to the more stable product.

  DOI：

  10.1021/jo005595v