(2R,3R,6R)-6-Allyl-2-hydroxymethyl-3,6-dihydro-2H-pyran-3-ol | 158780-35-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: (2R,3R,6R)-6-Allyl-2-hydroxymethyl-3,6-dihydro-2H-pyran-3-ol
• 英文别名: (2R,3R,6R)-2-(hydroxymethyl)-6-prop-2-enyl-3,6-dihydro-2H-pyran-3-ol
• CAS: 158780-35-9
• 化学式: C₉H₁₄O₃
• 分子量: 170.208
• InChiKey: PEAYPDCOVFUQMY-IWSPIJDZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.24
• 重原子数：
  12.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  49.69
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (2R,3R,6R)-6-Allyl-2-hydroxymethyl-3,6-dihydro-2H-pyran-3-ol 在 咪唑 、 4-二甲氨基吡啶 、 N,N-二甲基丙烯基脲 、 potassium fluoride 、 sodium periodate 、 四氧化锇 、 正丁基锂 、 N-甲基吲哚酮 、 potassium hydrogencarbonate 、 叔丁基二甲基氯硅烷 、 N,N'-二环己基碳二亚胺 、 六甲基二硅氮烷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 2-[(2R,3R,6S)-6-(tert-Butyl-dimethyl-silanyloxymethyl)-2-(2-oxo-ethyl)-3,6-dihydro-2H-pyran-3-yl]-propionic acid methyl ester
  参考文献：
  名称：

  A synthetic approach to the tricyclic system of forskolin from D-galactose

  摘要：

  The synthesis of the tricyclic system of forskolin by an intramolecular Diels-Alder reaction is described, starting from tri-O-acetyl-D-galactal.

  DOI：

  10.1016/s0040-4039(00)73468-x
• 作为产物：
  描述：

  3-(4',6'-di-O-acetyl-2',3'-dideoxy-α-D-threo-hex-2'-enopyranosyl)-1-propene 在 三乙胺 作用下， 以 甲醇 、 水 为溶剂， 生成 (2R,3R,6R)-6-Allyl-2-hydroxymethyl-3,6-dihydro-2H-pyran-3-ol
  参考文献：
  名称：

  A synthetic approach to the tricyclic system of forskolin from D-galactose

  摘要：

  The synthesis of the tricyclic system of forskolin by an intramolecular Diels-Alder reaction is described, starting from tri-O-acetyl-D-galactal.

  DOI：

  10.1016/s0040-4039(00)73468-x

文献信息

• Allyl C-glycosidations of totally unprotected glycals and allyltrimethylsilane with trimethylsilyl trifluoromethanesulfonate (TMSOTf)
  作者：Kazunobu Toshima、Toru Ishizuka、Goh Matsuo、Masaya Nakata

  DOI：10.1016/s0040-4039(00)77276-5

  日期：1994.8

  Allyl C-glycosidations of the totally unprotected glycals, L-rhamnal (1), D-glucal (2), D-galactal (3) and D-fucal (4), with allyltrimethylsilane (5) using TMSOTf proceeded much more effectively than those of the corresponding acetylated glycals 10∼13 to furnish the unprotected and 2,3-unsaturated allyl α-C-glycosides 6∼9 in high yields, respectively.

  烯丙基Ç的完全未保护的烯糖的-glycosidations，L-rhamnal（1），d-己烯糖（2），d半乳醛（3）和d-fucal（4）中，用烯丙基三甲基硅烷（5使用将TMSOTf）进行更有力的它们分别以相应的乙酰化糖基10-13的残基高收率提供未保护的和2，3-不饱和烯丙基α- C-糖苷6-9。
• Aryl and Allyl <i>C</i>-Glycosidation Methods Using Unprotected Sugars
  作者：Kazunobu Toshima、Goh Matsuo、Toru Ishizuka、Yasunobu Ushiki、Masaya Nakata、Shuichi Matsumura

  DOI：10.1021/jo972146v

  日期：1998.4.1

  Practical and highly stereoselective aryl and allyl C-glycosidation methods using unprotected sugars as glycosyl donors have been developed. Aryl C-glycosidations of several unprotected 2-deoxy sugars with phenol and naphthol derivatives by the combined use of trimethylsilyl trifluoromethanesulfonate (TMSOTf)-AgClO4 or TMSOTf exclusively gave the corresponding unprotected o-hydroxyaryl beta-C-glycosides which appear in many biologically attractive aryl C-glycoside antibiotics as the key subunit. On the other hand, allyl C-glycosidations of several unprotected glycals with allyltrimethylsilane by TMSOTf afforded the corresponding unprotected and 2,3-unsaturated allyl alpha-C-glycosides in high yields which are versatile synthetic intermediates for the syntheses of optically active natural products.