methyl 2-[(2S,3R,6S)-3-hydroxy-2-methyl-3,6-dihydro-2H-pyran-6-yl]acetate | 123976-40-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: methyl 2-[(2S,3R,6S)-3-hydroxy-2-methyl-3,6-dihydro-2H-pyran-6-yl]acetate
• CAS: 123976-40-9
• 化学式: C₉H₁₄O₄
• 分子量: 186.208
• InChiKey: MRWMVORXEUNCQP-XLPZGREQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 2-[(2S,3R,6S)-3-hydroxy-2-methyl-3,6-dihydro-2H-pyran-6-yl]acetate 在 Swern 、 溴 、 三乙胺 作用下， 生成 ((2S,6S)-4-Bromo-6-methyl-5-oxo-5,6-dihydro-2H-pyran-2-yl)-acetic acid methyl ester
  参考文献：
  名称：

  General Enantiospecific Route to Isochromanquinones. Synthesis of (-)-Nanaomycin D

  摘要：

  A general enantiospecific synthesis of isochromanquinones is presented. This entails an efficient synthesis of (3aS, 5S, 7aR)-7-bromo-3,3a,5,7a-tetrahydro-5-methyl-2H-furo[3,2-b]pyran-2-one (12) and ultimately the lithium agent 15 from commercially available L-rhamnose. Addition of 15 to the appropriate cyclobutenedione followed by thermolysis of the resulting cyclobutenone leads to the isochromanquinones 16a-c. In an analogous fashion the naturally occurring product, (-)-nanaomycin D, was synthesized. In addition, new methodology involving the ring expansion of iminocyclobutenones to aminophenols was discovered.

  DOI：

  10.1021/jo00104a004
• 作为产物：
  描述：

  1-(叔丁基二甲基硅氧基)-1-甲氧基乙烯 、 3,4-二-O-乙酰-1,5-酐-2,6-双脱氧-L-阿拉伯-己-1-糖醇 在 三氟化硼乙醚 作用下， 以 甲苯 为溶剂， 反应 1.5h， 生成 methyl 2-[(2R,3R,6S)-3-hydroxy-2-methyl-3,6-dihydro-2H-pyran-6-yl]acetate 、 methyl 2-[(2S,3R,6S)-3-hydroxy-2-methyl-3,6-dihydro-2H-pyran-6-yl]acetate
  参考文献：
  名称：

  天然存在的格拉纳汀的全合成

  摘要：

  通过连接手性左手片段和右手片段（5）和（10），然后将所得产物（11）内酯化和氧化性O-去甲基化，合成了天然花青素（1）。

  DOI：

  10.1039/c39890000354

文献信息

• OKAZAKI, KOUSUKE;NOMURA, KEIICHI;YOSHII, EIICHI, J. CHEM. SOC. CHEM. COMMUN.,(1989) N, C. 354-356
  作者：OKAZAKI, KOUSUKE、NOMURA, KEIICHI、YOSHII, EIICHI

  DOI：——

  日期：——
• Total synthesis of naturally occurring granaticin
  作者：Kousuke Okazaki、Keiichi Nomura、Eiichi Yoshii

  DOI：10.1039/c39890000354

  日期：——

  Natural granaticin (1) has been synthesized by joining the chiral left and right fragments, (5) and (10), and subsequent lactonization of the resulting product (11) and oxidative O-demethylation.

  通过连接手性左手片段和右手片段（5）和（10），然后将所得产物（11）内酯化和氧化性O-去甲基化，合成了天然花青素（1）。
• General Enantiospecific Route to Isochromanquinones. Synthesis of (-)-Nanaomycin D
  作者：Michael P. Winters、Michael Stranberg、Harold W. Moore

  DOI：10.1021/jo00104a004

  日期：1994.12

  A general enantiospecific synthesis of isochromanquinones is presented. This entails an efficient synthesis of (3aS, 5S, 7aR)-7-bromo-3,3a,5,7a-tetrahydro-5-methyl-2H-furo[3,2-b]pyran-2-one (12) and ultimately the lithium agent 15 from commercially available L-rhamnose. Addition of 15 to the appropriate cyclobutenedione followed by thermolysis of the resulting cyclobutenone leads to the isochromanquinones 16a-c. In an analogous fashion the naturally occurring product, (-)-nanaomycin D, was synthesized. In addition, new methodology involving the ring expansion of iminocyclobutenones to aminophenols was discovered.