4,6-O-isopropylidene-D-glucopyranose | 53691-70-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: 4,6-O-isopropylidene-D-glucopyranose
• 英文别名: 4,6-O-isopropylidene-D-glucose；4,6-O-Isopropyliden-D-glucopyranose；4,6-Isopropyliden-D-glucopyranose；4,6-O-Isopropyliden-D-glucose；(4aR,7R,8R,8aS)-2,2-dimethyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine-6,7,8-triol
• CAS: 53691-70-6；53691-71-7；68791-07-1；68791-08-2；70834-21-8；70834-22-9；70834-23-0；70834-24-1；70834-25-2
• 化学式: C₉H₁₆O₆
• 分子量: 220.222
• InChiKey: MHATXBSMGQDNJD-RTRLPJTCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  88.4
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4,6-O-isopropylidene-D-glucopyranose 在 吡啶 、 sodium hydroxide 、 sodium periodate 、 对甲苯磺酸 作用下， 以 四氢呋喃 为溶剂， 反应 5.25h， 生成 (+)-(4R-cis)(Z)-2,2-dimethyl-5-<3-(1,3-dioxan-2-yl)-1-propenyl>-1,3-dioxolane-4-methanol benzoate
  参考文献：
  名称：

  Enantiospecific syntheses of leukotrienes C4, D4, and E4, and [14,15-3H2]leukotriene E4 dimethyl ester

  摘要：

  DOI：

  10.1021/ja00349a053
• 作为产物：
  描述：

  4,6-O-异亚丙基-D-葡萄糖醛 在 叔丁基过氧化氢 、 MoO₂(acac)2 作用下， 以 正壬烷 、 甲苯 为溶剂， 反应 24.0h， 生成 4,6-O-isopropylidene-D-glucopyranose 、 4,6-O-isopropylidene-D-mannopyranose
  参考文献：
  名称：

  钼催化的立体选择性串联环氧化-乙醇的醇解/水解

  摘要：

  钼催化剂是用于葡糖和半乳糖衍生物的串联环氧化/醇解或环氧化/水解的有效且选择性的催化剂。在葡糖衍生物中，选择性主要受糖基位置3上的烯丙基取代基控制，通常获得在羟基被保护时最初衍生自α-环氧化物（葡萄糖）的产物，而衍生自β的产物。 -环氧化物（甘露）主要是在未保护的情况下获得的。在半乳衍生物中，酯选择性始终很高，可以得到α-环氧化物（半乳酸酯），并且与保护基团无关。

  DOI：

  10.1002/adsc.201000614

文献信息

• Reaction of cyclic ketals with ceric ammonium nitrate in acetonitrile/water
  作者：Emiliano Manzo、Gaspare Barone、Emiliano Bedini、Alfonso Iadonisi、Lorenzo Mangoni、Michelangelo Parrilli

  DOI：10.1016/s0040-4020(01)01006-7

  日期：2002.1

  performing the hydrolysis of cyclic acetals and ketals under basic or mildly alkaline conditions by ceric ammonium nitrate (CAN) in MeCN/H2O or in 10% aq. methanol is rejected. However a role for Ce(IV) as Lewis acid is evidenced at pH 4.4. Under these conditions, which allow hydrolysis of cyclic ketals leaving glycosidic bonds unaltered, a selectivity of ketal cleavage due to steric hindrance is also

  在碱性或弱碱性条件下，通过硝酸铈铵（CAN）在MeCN / H 2 O或10％水溶液中进行环状缩醛和缩酮水解的可能性。甲醇被拒绝。然而，在pH 4.4下证明了Ce（IV）作为路易斯酸的作用。在这些条件下，允许环缩酮水解而糖苷键保持不变，还可以观察到由于空间位阻而引起的缩酮切割的选择性。当丙酮/水代替MeCN / H 2 O作为溶剂时，可获得相似的收率。
• David, Serge; Estramareix, Bernard; Fischer, Jean-Claude, Journal of the Chemical Society. Perkin transactions I, 1982, # 9, p. 2131 - 2138
  作者：David, Serge、Estramareix, Bernard、Fischer, Jean-Claude、Therisod, Michel

  DOI：——

  日期：——
• Manzo, Emiliano; Barone, Gaspare; Parrilli, Michelangelo, Synlett, 2000, # 6, p. 887 - 889
  作者：Manzo, Emiliano、Barone, Gaspare、Parrilli, Michelangelo

  DOI：——

  日期：——
• Synthesis of salacinol
  作者：Hideya Yuasa、Jun Takada、Hironobu Hashimoto

  DOI：10.1016/s0040-4039(00)01129-1

  日期：2000.8

  Salacinol, a new type of alpha-glucosidase inhibitor discovered from the antidiabetic herb, was synthesized for the first time. Under the strategy that salacinol would be synthesized by the coupling reaction between 1,4-epithio-D-arabinitol and the cyclic sulfate of an erythritol derivative, the model coupling reactions between tetrahydrothiophene and versatile cyclic sulfate derivatives were undertaken. These experiments indicated that the 1,3-diol of the cyclic sulfate should be protected with the isopropylidene group, otherwise, even the benzylidene-protected cyclic sulfate decomposed during the reaction. Thus, the salacinol was synthesized using the cyclic sulfate of 1,3-O-isopypropylidene-D-erythritol. The resulting coupling product was deisopropylidenated to afford salacinol. A diastereomer of salacinol was also synthesized. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Synthesis of monosaccharide-fused azetidines
  作者：Thierry Michaud、Josette Chanet-Ray、Sithan Chou、Jacques Gelas

  DOI：10.1016/s0008-6215(97)00015-3

  日期：1997.4

  Primary amines reacted upon 4,6-ditosylates of glucopyranosides to give an azetidine ring fused on C-4 and C-6 of the pyranose ring. On the other hand, the 4,6-ditosylate of benzyl mannopyranoside led to the 4,6-diamino-4,6-dideoxy derivative in a good yield. All the compounds and their precursors were identified by H-1 and C-13 NMR spectroscopy. Assignments of proton signals were made unambiguously using homodecoupling experiments. (C) 1997 Elsevier Science Ltd.