(2R,3S,4S)-6-hepten-2,3,4-triol | 155154-09-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2R,3S,4S)-6-hepten-2,3,4-triol
• 英文别名: (2R,3S,4S)-hept-6-ene-2,3,4-triol
• CAS: 155154-09-9
• 化学式: C₇H₁₄O₃
• 分子量: 146.186
• InChiKey: MKUDLFMBZAEQMN-VQVTYTSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  60.7
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2R,3S,4S)-6-hepten-2,3,4-triol 在 4-二甲氨基吡啶 臭氧 、 三苯基膦 作用下， 以 吡啶 为溶剂， 反应 19.0h， 生成 1,3,4-Tri-O-acetyl-2-deoxy-α/β-D-ribohexopyranose
  参考文献：
  名称：

  Indium-mediated allylation of aldehydes: A convenient route to 2-deoxy and 2,6-dideoxy carbohydrates

  摘要：

  The allylation of protected polyhydroxy aldehydes 1 and 14 has been achieved by indium metal with ultrasound promotion generating the diastereomeric pair of homoallylic polyols 3, 4 and 16, 17 respectively with moderate to good stereoselectivity. Pursuing this allylation strategy with the corresponding deprotected polyhydroxy aldehydes led to the same pair of homoallylic polyols but with a quite different ratio of the diastereomers generated. The polyols were further transformed to 2-deoxy (5 and 6) and 2,6-dideoxy (18 and 19) carbohydrates by ozonolysis.

  DOI：

  10.1016/s0040-4020(01)80790-0
• 作为产物：
  描述：

  (4S,5R,6R)-5,6-bis(methoxymethoxy)hept-1-en-4-ol 在 silica gel impregnated with phosphomolybdic acid 作用下， 反应 8.0h， 以74%的产率得到(2R,3S,4S)-6-hepten-2,3,4-triol
  参考文献：
  名称：

  脂质内酯及其C9差向异构体的首次全合成

  摘要：

  摘要 本文介绍了以Keck不对称烯丙基化/ Barbier烯丙基化和烯烃交叉复分解为关键步骤的生物活性脂肽内酯和C9-表-脂内酯的首次全合成。 本文介绍了以Keck不对称烯丙基化/ Barbier烯丙基化和烯烃交叉复分解为关键步骤的生物活性脂肽内酯和C9-表-脂内酯的首次全合成。

  DOI：

  10.1055/s-0033-1340314

文献信息

• Stereochemistry of the reactions of substituted allylboronates with chiral aldehydes. Factors influencing aldehyde diastereofacial selectivity
  作者：William R. Roush、Michael A. Adam、Alan E. Walts、David J. Harris

  DOI：10.1021/ja00272a043

  日期：1986.6
• ROUSH, W. R.;BROWN, R. J.;DIMARE, M., J. ORG. CHEM., 1983, 48, N 25, 5083-5093
  作者：ROUSH, W. R.、BROWN, R. J.、DIMARE, M.

  DOI：——

  日期：——
• Indium-mediated allylation of aldehydes: A convenient route to 2-deoxy and 2,6-dideoxy carbohydrates
  作者：Wolfgang H. Binder、Reinhard H. Prenner、Walther Schmid

  DOI：10.1016/s0040-4020(01)80790-0

  日期：1994.1

  The allylation of protected polyhydroxy aldehydes 1 and 14 has been achieved by indium metal with ultrasound promotion generating the diastereomeric pair of homoallylic polyols 3, 4 and 16, 17 respectively with moderate to good stereoselectivity. Pursuing this allylation strategy with the corresponding deprotected polyhydroxy aldehydes led to the same pair of homoallylic polyols but with a quite different ratio of the diastereomers generated. The polyols were further transformed to 2-deoxy (5 and 6) and 2,6-dideoxy (18 and 19) carbohydrates by ozonolysis.
• First Total Synthesis of Lippialactone and Its C9 Epimer
  作者：Palakodety Radha Krishna、Rajesh Nomula、Ramesh Kunde

  DOI：10.1055/s-0033-1340314

  日期：——

  Abstract This paper describes the first total synthesis of bioactive lippialactone and C9-epi-lippialactone adopting Keck asymmetric allylation/Barbier allylation and olefin cross-metathesis as the key steps. This paper describes the first total synthesis of bioactive lippialactone and C9-epi-lippialactone adopting Keck asymmetric allylation/Barbier allylation and olefin cross-metathesis as the key

  摘要 本文介绍了以Keck不对称烯丙基化/ Barbier烯丙基化和烯烃交叉复分解为关键步骤的生物活性脂肽内酯和C9-表-脂内酯的首次全合成。 本文介绍了以Keck不对称烯丙基化/ Barbier烯丙基化和烯烃交叉复分解为关键步骤的生物活性脂肽内酯和C9-表-脂内酯的首次全合成。