3-(4,6-di-O-acetyl-2,3-dideoxy-β-D-threo-hex-2-enopyranosyl)-1-propene | 129230-33-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 3-(4,6-di-O-acetyl-2,3-dideoxy-β-D-threo-hex-2-enopyranosyl)-1-propene
• 英文别名: [(2R,3R,6S)-3-acetyloxy-6-prop-2-enyl-3,6-dihydro-2H-pyran-2-yl]methyl acetate
• CAS: 129230-33-7
• 化学式: C₁₃H₁₈O₅
• 分子量: 254.283
• InChiKey: MPRBSSKQJFGMFR-YNEHKIRRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.38
• 重原子数：
  18.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  61.83
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  phenyl-2,4-di-O-acetyl-2,3-dideoxy-1-thio-α-D-threo-hex-2-eno-pyranoside 、 烯丙基三丁基锡 生成 3-(4,6-di-O-acetyl-2,3-dideoxy-β-D-threo-hex-2-enopyranosyl)-1-propene
  参考文献：
  名称：

  MARCO-CONTELLES, J. L.;FERNANDEZ, C.;GOMEZ, ANA;MARTIN-LEON, N., TETRAHEDRON LETT., 31,(1990) N0, C. 1467-1470

  摘要：

  DOI：

文献信息

• Iodine-Catalyzed Stereoselective Synthesis of Allylglycosides, Glycosyl Cyanides and Glycosyl azides
  作者：J. S. Yadav、B. V. S. Reddy、C. Venkateshwar Rao、Pratap. K. Chand、A. R. Prasad

  DOI：10.1055/s-2001-17438

  日期：——

  Iodine efficiently catalyzes the glycosidation of glycals with allyltrimethylsilane, trimethylsilyl cyanide and trimethylsilyl azide in dichloromethane at ambient temperature to afford the corresponding 2,3-unsaturated allyl glycosides, glycosyl cyanides and glycosyl azides in excellent yields with high α-selectivity.

  碘高效催化糖烯与烯丙基三甲基硅烷、三甲基硅基氰和三甲基硅基叠氮在室温下二氯甲烷中反应，以高产率和高α-选择性得到了相应的2,3-不饱和烯丙基糖苷、糖基氰化物和糖基叠氮化合物。
• Environmentally compatible C-glycosidation of glycals using montmorillonite K-10
  作者：Kazunobu Toshima、Naoki Miyamoto、Goh Matsuo、Masaya Nakata、Shuichi Matsumura

  DOI：10.1039/cc9960001379

  日期：——

  The C-glycosidations of glycal acetates 1–4 with allyltrimethylsilane 5, vinyloxytrimethylsilane 6 or isopropenyl acetate 7 using montmorillonite K-10 as an environmentally acceptable and inexpensive industrial catalyst under mild conditions proceed effectively to give the corresponding 2,3-unsaturated C-glycosides in high yields.

  甘油醛乙酸酯1-4在温和条件下，以蒙脱土K-10作为环境友好且经济的工业催化剂，与烯丙基三甲基硅烷5、乙烯氧基三甲基硅烷6或异丙烯基乙酸酯7进行C-糖基化反应，高效地生成了相应的2,3-不饱和C-糖苷，产率极高。
• LiBF4-mediated C-glycosylation of glycals with allyltrimethylsilane: a facile synthesis of allyl C-glycosylic compounds
  作者：Jhillu S Yadav、Basi V.Subba Reddy、Lagisetti Chandraiah、Katham Srinivasa Reddy

  DOI：10.1016/s0008-6215(01)00087-8

  日期：2001.5

  The treatment of glycals with allyltrimethylsilane in the presence of lithium tetrafluoroborate in acetonitrile gave the corresponding allyl 2,3-unsaturated C-glycosylic compounds in excellent yields with high anomeric selectivity.

  在四氟硼酸锂在乙腈中存在的条件下，用烯丙基三甲基硅烷处理糖基得到了相应的烯丙基2,3-不饱和C-糖基化合物，具有优异的收率和高的异头选择性。
• Bi(OTf)₃as Novel and Efficient Catalyst for the Stereoselective Synthesis of<i>C</i>-Pseudoglycals
  作者：J. S. Yadav、B. V. S. Reddy、K. Srinivasa Reddy、L. Chandraiah、V. Sunitha

  DOI：10.1055/s-2004-831187

  日期：——

  d-Glycals undergo smoothly allylic rearrangement with allyltrimethylsilane and trimethylsilyl cyanide in the presence of catalytic amount of bismuth triflate to afford the corresponding 2,3-unsaturated allyl glycosides and glycosyl cyanides in excellent yields with high α-selectivity.

  d-甘露醇在催化量的三氟甲磺酸铋存在下，与烯丙基三甲基硅烷和三甲基硅基氰化物顺利进行烯丙位重排反应，高效地生成相应的2,3-不饱和烯丙基糖苷和糖基氰化物，产率优异且具有高度的α-选择性。
• Stereoselective Synthesis of α- and β-C-Glycosides by Addition of Titanium Enolates to Glycals
  作者：Pedro Romea、Fèlix Urpí、Erik Gálvez、Igor Larrosa

  DOI：10.1055/s-0029-1218279

  日期：2009.11

  Both α- and β-C-glycosides can be prepared by SnCl4-mediated addition of titanium enolates from N-acetylthiazolidine­thiones to glycals. Subsequent removal of the chiral auxiliary provides enantiomerically pure fragments that are useful for the synthesis of natural products.

  通过 SnCl4 介导的 N-acetylthiazolidinethiones 与甘氨酸的钛烯醇加成，可以制备 δ- 和 δ²-C 糖苷。随后去除手性助剂可得到对映体纯的片段，这些片段可用于天然产物的合成。