n-propyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside | 6802-30-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: n-propyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside
• 英文别名: propyl-(tetra-O-acetyl-β-D-glucopyranoside)；Propyl-(tetra-O-acetyl-β-D-glucopyranosid)；n-Propyl 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranoside；[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-propoxyoxan-2-yl]methyl acetate
• CAS: 6802-30-8
• 化学式: C₁₇H₂₆O₁₀
• 分子量: 390.387
• InChiKey: CWUMLQVHOLFZBX-NQNKBUKLSA-N

物化性质

• 熔点：
  102-103 °C
• 沸点：
  434.4±45.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  27
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  124
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  n-propyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 在 甲醇 、 sodium methylate 作用下， 生成 丙基 BETA-D-吡喃葡萄糖苷
  参考文献：
  名称：

  Veibel; Eriksen, Bulletin de la Societe Chimique de France, 1936, vol. <5> 3, p. 277,281

  摘要：

  DOI：
• 作为产物：
  描述：

  丙醇 、 2,3,4,6-四乙酰氧基-alpha-D-吡喃葡萄糖溴化物 在 silver carbonate 作用下， 生成 n-propyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside
  参考文献：
  名称：

  Veibel; Eriksen, Bulletin de la Societe Chimique de France, 1936, vol. <5> 3, p. 277,281

  摘要：

  DOI：

文献信息

• BiBr₃-Promoted Activation of Peracetylated Glycosyl Iodides: Straightforward Access to Synthetically Useful 2-<i>O</i>-Deprotected Allyl Glycosides
  作者：Antonello Pastore、Matteo Adinolfi、Alfonso Iadonisi

  DOI：10.1002/ejoc.200800914

  日期：2008.12

  anomeric activation of acetylated glycosyl iodides. This reactivity can be exploited for straightforward access to allyl glycosides unprotected at the O-2 position. The reported protocol appears to be convenient in comparison with the pre-existing ones in that shorter experimental times are needed and the use of strong acids is avoided. Suitable structural features of substrates (6-deoxy sugars or use

  亚化学计量量的 BiBr3 能够促进乙酰化糖基碘的异头活化。这种反应性可用于直接获得在 O-2 位置未受保护的烯丙基糖苷。与先前存在的协议相比，报告的协议似乎很方便，因为需要更短的实验时间并且避免使用强酸。底物的合适结构特征（6-脱氧糖或使用苯甲酰基或甲氧基羰基 2-O 参与基团）将过程切换到优先糖苷化，而不会在 O-2 位置脱保护。（© Wiley-VCH Verlag GmbH & Co. KGaA , 69451 德国魏因海姆, 2008)
• Ferric chloride, an anomerization catalyst for the preparation of alkyl α-glycopyranosides
  作者：Norihiro Ikemoto、Oak Kyung Kim、Lee-Chiang Lo、Vunnam Satyanarayana、Mayland Chang、Koji Nakanishi

  DOI：10.1016/s0040-4039(00)74242-0

  日期：1992.7

  Anhydrous FeCl3 in CH2Cl2 has been found to readily anomerize β-glycopyranosides to their corresponding α-anomers in good yields and selectivities at room temperatures. Acetyl- and benzoyl-protected oxygen sugars yielded the best results.

  已经发现CH 2 Cl 2中的无水FeCl 3可以在室温下以良好的产率和选择性将β-糖吡喃糖苷容易地异构化为其相应的α-端基异构体。乙酰基和苯甲酰基保护的氧糖产生了最好的结果。
• Gas Chromatographic Investigation of the Boron Trifluoride Etherate-Induced Formation and Anomerization of Glucopyranosides
  作者：Ulf Ellervik、Karl Jansson、Göran Magnusson

  DOI：10.1080/07328309808002351

  日期：1998.5.1

  Boron trifluoride etherate-induced glucosylation of methanol, 1-propanol, 2-propanol, 2-bromoethanol, and 3-bromo-2-(bromomethyl)propan-1-ol, using 1,2,3,4,6-penta-O-acetyl-beta-D-glucopyranose as donor, gave the corresponding beta-glucopyranosides. The alpha-glucosides and 1,2,3,4,6-penta-O-acetyl-alpha-D-glucopyranose were formed as byproducts in varying amounts, according to GLC analysis. The propensity of the different glucopyranosides to anomerize was determined in separate experiments.
• Lindberg, Acta Chemica Scandinavica (1947), 1949, vol. 3, p. 151,152
  作者：Lindberg

  DOI：——

  日期：——