1,2-5,6-di-O-isopropylidene-3-O-(N-phenylcarbamoyl)-α-D-glucofuranose | 34368-65-5

• 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: 1,2-5,6-di-O-isopropylidene-3-O-(N-phenylcarbamoyl)-α-D-glucofuranose
• 英文别名: [(3aR,5R,6S,6aR)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-yl] N-phenylcarbamate
• CAS: 34368-65-5
• 化学式: C₁₉H₂₅NO₇
• 分子量: 379.41
• InChiKey: YSKLOZAHUPIAPI-IBEHDNSVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  84.5
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1,2-5,6-di-O-isopropylidene-3-O-(N-phenylcarbamoyl)-α-D-glucofuranose 在 硫酸 、 氢溴酸 、 silver trifluoromethanesulfonate 作用下， 以 1,4-二氧六环 、 吡啶 、 二氯甲烷 、 水 、 溶剂黄146 为溶剂， 生成 (-)-menthyl 2,4,6-tri-O-acetyl-3-O-(N-phenylcarbamoyl)-β-D-glucopyranoside
  参考文献：
  名称：

  Kunz, Horst; Guenther, Wolfgang, Angewandte Chemie, 1988, vol. 100, # 8, p. 1118 - 1119

  摘要：

  DOI：
• 作为产物：
  描述：

  异氰酸苯酯 、 双丙酮葡萄糖 在 4-二甲氨基吡啶 作用下， 以 甲苯 为溶剂， 反应 3.0h， 以92%的产率得到1,2-5,6-di-O-isopropylidene-3-O-(N-phenylcarbamoyl)-α-D-glucofuranose
  参考文献：
  名称：

  Synthesis of β-d-mannosides from β-d-glucosides via an intramolecular Sn2 reaction at C-2

  摘要：

  The selective synthesis of beta-D-mannosides was achieved by first synthesizing beta-D-glucosides that carry a N-phenylcarbamoyl protecting group at O-3. These derivatives were transformed into the corresponding beta-D-mannosides by intramolecular nucleophilic substitution with inversion of configuration at C-2, the O-triflyl group being the leaving group. Subsequent intramolecular attack of the neighboring carbamoyl group resulted in the formation of the 2,3-carbonate of the desired beta-D-mannoside.

  DOI：

  10.1016/s0008-6215(00)90561-5

文献信息

• Kunz, Horst; Guenther, Wolfgang, Angewandte Chemie, 1988, vol. 100, # 8, p. 1118 - 1119
  作者：Kunz, Horst、Guenther, Wolfgang

  DOI：——

  日期：——
• Synthesis of β-d-mannosides from β-d-glucosides via an intramolecular Sn2 reaction at C-2
  作者：Wolfgang Günther、Horst Kunz

  DOI：10.1016/s0008-6215(00)90561-5

  日期：1992.4

  The selective synthesis of beta-D-mannosides was achieved by first synthesizing beta-D-glucosides that carry a N-phenylcarbamoyl protecting group at O-3. These derivatives were transformed into the corresponding beta-D-mannosides by intramolecular nucleophilic substitution with inversion of configuration at C-2, the O-triflyl group being the leaving group. Subsequent intramolecular attack of the neighboring carbamoyl group resulted in the formation of the 2,3-carbonate of the desired beta-D-mannoside.