(1R,2R,4R,6R)-2-methoxy-4-(phenylmethoxymethyl)-3,7-dioxabicyclo[4.1.0]heptane | 790667-27-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1R,2R,4R,6R)-2-methoxy-4-(phenylmethoxymethyl)-3,7-dioxabicyclo[4.1.0]heptane
• CAS: 790667-27-5
• 化学式: C₁₄H₁₈O₄
• 分子量: 250.295
• InChiKey: XFZYHAZELOODHL-AAVRWANBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  40.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1R,2R,4R,6R)-2-methoxy-4-(phenylmethoxymethyl)-3,7-dioxabicyclo[4.1.0]heptane 在 sodium hydroxide 作用下， 反应 2.0h， 以93%的产率得到methyl 6-O-benzyl-4-deoxy-α-L-altro-hexopyranoside
  参考文献：
  名称：

  Synthesis of 4-Deoxy-l-(and d-)hexoses from Chiral Noncarbohydrate Building Blocks

  摘要：

  4-Deoxy-L-hexoses were synthesized starting from our previously reported reagent 1 and (R)-benzyl glycidyl ether, which led in few steps to a substituted dihydropyran 6. The stereocontrolled hydroxylation of the latter afforded the corresponding 4-deoxy-L-hexoses 7a, 9, and 11. The same procedure, starting from (S)-benzyl glycidyl ether, enabled the preparation of their D-series enantiomers.

  DOI：

  10.1021/jo0493774
• 作为产物：
  描述：

  (R)-苄氧甲基环氧乙烷 在 吡啶 、 titanium(IV) isopropylate 、 三氟甲磺酸三甲基硅酯 、 TEA 、 镍 、 间氯过氧苯甲酸 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 127.08h， 生成 (1R,2R,4R,6R)-2-methoxy-4-(phenylmethoxymethyl)-3,7-dioxabicyclo[4.1.0]heptane
  参考文献：
  名称：

  Synthesis of 4-Deoxy-l-(and d-)hexoses from Chiral Noncarbohydrate Building Blocks

  摘要：

  4-Deoxy-L-hexoses were synthesized starting from our previously reported reagent 1 and (R)-benzyl glycidyl ether, which led in few steps to a substituted dihydropyran 6. The stereocontrolled hydroxylation of the latter afforded the corresponding 4-deoxy-L-hexoses 7a, 9, and 11. The same procedure, starting from (S)-benzyl glycidyl ether, enabled the preparation of their D-series enantiomers.

  DOI：

  10.1021/jo0493774

文献信息

• Synthesis of 4-Deoxy-<scp>l</scp>-(and <scp>d</scp>-)hexoses from Chiral Noncarbohydrate Building Blocks
  作者：Romualdo Caputo、Mauro De Nisco、Pasquale Festa、Annalisa Guaragna、Giovanni Palumbo、Silvana Pedatella

  DOI：10.1021/jo0493774

  日期：2004.10.1

  4-Deoxy-L-hexoses were synthesized starting from our previously reported reagent 1 and (R)-benzyl glycidyl ether, which led in few steps to a substituted dihydropyran 6. The stereocontrolled hydroxylation of the latter afforded the corresponding 4-deoxy-L-hexoses 7a, 9, and 11. The same procedure, starting from (S)-benzyl glycidyl ether, enabled the preparation of their D-series enantiomers.