Acetic acid (2R,3R,4S,5S,6S)-3-acetoxy-2-acetoxymethyl-5-iodo-6-((E)-(S)-1-prop-2-ynyl-but-2-enyloxy)-tetrahydro-pyran-4-yl ester | 192641-04-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Acetic acid (2R,3R,4S,5S,6S)-3-acetoxy-2-acetoxymethyl-5-iodo-6-((E)-(S)-1-prop-2-ynyl-but-2-enyloxy)-tetrahydro-pyran-4-yl ester
• 英文别名: [(2R,3R,4S,5S,6S)-3,4-diacetyloxy-6-[(E,4S)-hept-5-en-1-yn-4-yl]oxy-5-iodooxan-2-yl]methyl acetate
• CAS: 192641-04-6
• 化学式: C₁₉H₂₅IO₈
• 分子量: 508.307
• InChiKey: RUMNETDFCXRFLY-HSKKYDAOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  28
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  97.4
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  Acetic acid (2R,3R,4S,5S,6S)-3-acetoxy-2-acetoxymethyl-5-iodo-6-((E)-(S)-1-prop-2-ynyl-but-2-enyloxy)-tetrahydro-pyran-4-yl ester 在 三乙基硼 、 氧气 、 碘乙烷 作用下， 以 甲苯 为溶剂， 以37%的产率得到Acetic acid (2R,3S,4R,4aR,4bR,5S,8aS,9aS)-3-acetoxy-2-acetoxymethyl-7-iodo-5-methyl-3,4,4a,4b,5,8,8a,9a-octahydro-2H-benzo[4,5]furo[2,3-b]pyran-4-yl ester
  参考文献：
  名称：

  Tandem radical mediated 5-exo-trig, 6-endo-dig cyclization. Stereoselectivity, α-trimethylsilyl effect and the product spread — IV

  摘要：

  Stereochemistry and mechanism of the title reaction have been investigated. The reaction proceeds well in the (S) series. In the epimeric (R) series a product spread is usually observed. In either series olefin configuration is lost (7 examples), consistent with a freely rotating exocyclic radical intermediate. An alpha-trimethylsilyl group at the olefinic terminus enhances the selectivity of the radical cascade Spectroscopic evidence and MMX calculations suggest that the tandem annulation products of the (S) series are favoured thermodynamically, being more stable than those of the (R) series. Pyranoside (R)G2a is frozen in a half chair conformation. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00519-x
• 作为产物：
  描述：

  Acetic acid (2R,3R,4S,5S,6S)-3-acetoxy-2-acetoxymethyl-5-iodo-6-[(E)-(S)-1-(3-trimethylsilanyl-prop-2-ynyl)-but-2-enyloxy]-tetrahydro-pyran-4-yl ester 以71%的产率得到Acetic acid (2R,3R,4S,5S,6S)-3-acetoxy-2-acetoxymethyl-5-iodo-6-((E)-(S)-1-prop-2-ynyl-but-2-enyloxy)-tetrahydro-pyran-4-yl ester
  参考文献：
  名称：

  Tandem radical mediated 5-exo-trig, 6-endo-dig cyclization. Stereoselectivity, α-trimethylsilyl effect and the product spread — IV

  摘要：

  Stereochemistry and mechanism of the title reaction have been investigated. The reaction proceeds well in the (S) series. In the epimeric (R) series a product spread is usually observed. In either series olefin configuration is lost (7 examples), consistent with a freely rotating exocyclic radical intermediate. An alpha-trimethylsilyl group at the olefinic terminus enhances the selectivity of the radical cascade Spectroscopic evidence and MMX calculations suggest that the tandem annulation products of the (S) series are favoured thermodynamically, being more stable than those of the (R) series. Pyranoside (R)G2a is frozen in a half chair conformation. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00519-x