methyl 4,6-O-isopropylidene-2,3-di-O-methyl-α-D-glucopyranoside | 15354-38-8

• 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: methyl 4,6-O-isopropylidene-2,3-di-O-methyl-α-D-glucopyranoside
• CAS: 15354-38-8
• 化学式: C₁₂H₂₂O₆
• 分子量: 262.303
• InChiKey: HPRRWWKGVOFGLY-NZFPMDFQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.54
• 重原子数：
  18.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  55.38
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  methyl 4,6-O-isopropylidene-2,3-di-O-methyl-α-D-glucopyranoside 以 溶剂黄146 为溶剂， 反应 1.0h， 以95%的产率得到甲基 2,3-二-O-甲基-alpha-D-吡喃葡萄糖苷
  参考文献：
  名称：

  Synthesis of monosaccharide-fused azetidines

  摘要：

  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.

  DOI：

  10.1016/s0008-6215(97)00015-3
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 silver(l) oxide 、 碘甲烷 作用下， 生成 methyl 4,6-O-isopropylidene-2,3-di-O-methyl-α-D-glucopyranoside
  参考文献：
  名称：

  Jones, Canadian Journal of Chemistry, 1956, vol. 34, p. 840

  摘要：

  DOI：

文献信息

• Hydrogenolysis of the 4,6-O-Ketals of Glucopyranosides. Configuration-Dependent High Regio- and Stereo-Selectivity of the Diastereoisomeric Acetophenone Derivatives
  作者：J Hajko、G Szabovik、J Kerekgyarto、M Kajtar、A Liptak

  DOI：10.1071/ch9960357

  日期：——

  Hydrogenolysis (reductive cleavage) of the (R) isomers of the acetophenone 4,6-O-derivatives of glucopyranosides with LiAlH4/AlCl3 gives the 4-O-(1'-phenylethyl) ethers with (R) configuration; the corresponding (S) isomers produce the respective (R) 6-O-(1'-phenylethyl ) ethers are produced. The hydrogenolysis of other 4,6-O-ketals affords O 4 ether derivatives; the two diastereoisomeric 4,6-O-s-butylidene derivatives (cyclic ketals ) give O 4-ethers with the opposite absolute configuration. The stereoselectivity of these reactions is explained by the development of a four-centre transition state. The absolute configuration of the ethers has been determined by means of circular dichroism measurements.

  用 LiAlH4/AlCl3 对葡萄糖苷的苯乙酮 4,6-O 衍生物的 (R) 异构体进行氢解（还原裂解），可得到 (R) 构型的 4-O-(1'-苯基乙基) 醚；相应的 (S) 异构体可生成相应的 (R) 6-O-(1'-苯基乙基 ) 醚。其他 4,6-O-酮的氢解反应会产生 O 4 醚衍生物；两种非对映异构的 4,6-O-亚丁基衍生物（环酮）会产生绝对构型相反的 O 4 醚。这些反应的立体选择性可通过四中心过渡态的发展来解释。醚的绝对构型是通过圆二色性测量确定的。