(2S,4S)-1,5-dichloro-2,4-pentanediol | 136030-29-0

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 卤代醇
• 英文名称: (2S,4S)-1,5-dichloro-2,4-pentanediol
• 英文别名: (2S,4S)-1,5-dichloro-penta-2,4-diol；(2S,4S)-1,5-dichlorpentane-2,4-diol；(2S,4S)-1,5-dichloropentane-2,4-diol
• CAS: 136030-29-0
• 化学式: C₅H₁₀Cl₂O₂
• 分子量: 173.039
• InChiKey: QJULQKBJMRGSCF-WHFBIAKZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  9
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2S,4S)-1,5-dichloro-2,4-pentanediol 在 正丁基锂 、 4-硝基[1,1-联苯]-2-羧酸 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 生成 (1R,4S)-(-)-4-triisopropylsilyloxy-1-hydroxycyclopent-2-ene
  参考文献：
  名称：

  Synthesis of cyclic 1,3-diols as scaffolds for spatially directed libraries

  摘要：

  一系列1,3-二醇已经合成并用于创建一个空间多样化化合物的试验库。

  DOI：

  10.1039/c6ob00598e
• 作为产物：
  描述：

  2,4-戊二酮,1,5-二氯 以 甲醇 为溶剂， 以75%的产率得到(2S,4S)-1,5-dichloro-2,4-pentanediol
  参考文献：
  名称：

  立体控制合成的C1-C10结构单元（“西南部分”），用于多烯多元醇抗生素菲林III和戊霉素的非天然对映异构体：形成磺内酯的封闭环易位基，用于保护均丙醇。

  摘要：

  高烯丙基，巴豆酸和高烯丙基ethenesulfonate中间的双重闭环复分解甲得到不饱和内酯和含有磺内酯中间体乙。内酯通过非对映选择性的1,4-加成甲硅烷基铜酸酯改性，然后除去磺内酯以提供碘代碳酸化顺式（→  C）的均丙醇。随后进行非对映选择性醛醇缩合（→→  D）。

  DOI：

  10.1002/ejoc.201400145

文献信息

• A practical synthesis of A-ring precursors for 19-nor-1α,25-dihydroxyvitamin D3 analogues
  作者：Sheng-Ze Zhou、Sofia Anné、Maurits Vandewalle

  DOI：10.1016/0040-4039(96)01700-5

  日期：1996.10

  A convergent, more practical route to the A-ring precursors 3 and 5 starting from enantiopure (2S,4S)-1,2:4,5-diepoxypentane (11) is described.

  描述了从对映纯（2S，4S）-1，2：4，5-二环氧戊烷（11）开始向A环前体3和5收敛的，更实用的途径。
• Stereodivergent Synthesis of Enantioenriched 4-Hydroxy-2-cyclopentenones
  作者：Gurpreet Singh、Angelica Meyer、Jeffrey Aubé

  DOI：10.1021/jo402539p

  日期：2014.1.3

  Protected 4-hydroxycyclopentenones (4-HCPs) constitute an important class of intermediates in chemical synthesis. A route to this class of compound has been developed. Key steps include Noyori reduction (which establishes the stereochemistry of the product), ring-closing metathesis, and simple functional group conversions to provide a set of substituted 4-HCPs in either enantiomeric form.
• Enantiospecific Total Synthesis of <scp>l</scp>-2‘,3‘-Dideoxyisonucleosides via Regioselective Opening of Optically Active <i>C</i>₂-Symmetric 1,4-Pentadiene Bis-epoxide¹
  作者：Michael E. Jung、Oliver Kretschik

  DOI：10.1021/jo9721655

  日期：1998.5.1

  A new method for the synthesis of L-2',3'-dideoxyisonucleosides is described. The readily available, optically active C-2-symmetric bis-epoxide (2S,4S)-1,2:4,5-diepoxypentane (5) was prepared by a short route from readily available starting materials. The key step of the new synthesis is the opening of 5 with nucleophiles, which proceeds highly regioselectively; e.g., reaction with sodium sulfide affords a 5:1 mixture of the tetrahydrothiophenediol 9a and the tetrahydrothiopyrandiol 14, and reaction with sodium hydroxide gives exclusively the tetrahydrofurandiol 9b via a preferred 5-exo cyclization. These five-membered diols 9a,b can be converted in only four steps into the modified dideoxyuridine and adenosine isonucleosides 4a-c, one of which (4c) has shown good antiviral activity. In addition, we have examined the opening of the analogous six carbon bis-epoxide, (2S,5S)-1,2:5,6-diepoxyhexane (23), which affords a 3:1 mixture of the hexahydrothiepinediol 24 and the tetrahydrothiopyrandiol 25 with sodium sulfide via a preferred 7-endo cyclization. An alternate route to these two optically active bis-epoxides 5 and 23 was also examined, namely the asymmetric dihydroxylation of 1,4-pentadiene and 1,5-hexadiene followed by selective sulfonylation and epoxide : formation. The asymmetric reaction produces a nearly 1:1 mixture of optically active and meso tetrols, e.g., 28-9 and 32-3. Unfortunately, the tetrols, their simple derivatives, and the final sulfonates and epoxides could not be readily separated by Rnv simple means.
• PREPARATION OF (R,R)-1,2:4,5-DIEPOXYPENTANE
  作者：Rychnovsky, Scott D.、Griesgraber, George、Powers, Jay P.

  DOI：10.15227/orgsyn.077.0001

  日期：——
• Optically pure 1,3-diols from (2R,4R)- and (2S,4S)-1,2:4,5-diepoxypentane
  作者：Scott D. Rychnovsky、George Griesgraber、Sam Zeller、Donald J. Skalitzky

  DOI：10.1021/jo00017a032

  日期：1991.8

  Optically pure (> 97% ee) (2R,4R)-1,2:4,5-diepoxypentane (1) and its enantiomer can be prepared in three steps from 2,4-pentanedione without the need for chromatographic purification. Diepoxide 1 is an efficient precursor to a wide variety of optically pure syn and anti 1,3-diols. Reaction with excess nucleophile gives symmetric[GRAPHICS]anti 1,3-diols in good yield. Reaction with a slight excess of alkyllithium under Ganem's conditions gives the monoepoxides 5 in good yield. Addition of a second nucleophile to monoepoxide 5 gives asymmetric anti 1,3-diols. Mitsunobu inversion of monoepoxide 5 followed by addition of a second nucleophile gives syn 1,3-diols. Optically pure syn and anti 1,3-diols are available from diepoxide 1 in one to three steps and good overall yield.