<3S-(3α,4β,5β)>-3-(acetylamino)-3,4-dihydro-4-hydroxy-5-(hydroxymethyl)-2(5H)-furanone | 24695-37-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: <3S-(3α,4β,5β)>-3-(acetylamino)-3,4-dihydro-4-hydroxy-5-(hydroxymethyl)-2(5H)-furanone
• 英文别名: N-acetylpolyoxaminolactone；N-[(3S,4S,5S)-4-hydroxy-5-(hydroxymethyl)-2-oxooxolan-3-yl]acetamide
• CAS: 24695-37-2
• 化学式: C₇H₁₁NO₅
• 分子量: 189.168
• InChiKey: SFSOCLFOPIFBBR-HCWXCVPCSA-N

物化性质

• 沸点：
  596.0±50.0 °C(Predicted)
• 密度：
  1.44±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  95.9
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (E)-3-<(4S-trans)-2,2-dimethyl-5-<(phenylmethoxy)methyl>-1,3-dioxolan-4-yl>-2-propenol 在 ruthenium trichloride 、 氢氧化钾 、 sodium hydroxide 、 sodium periodate 、 sodium hydride 、 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 四氯化碳 、 二氯甲烷 、 水 、 乙腈 、 xylene 为溶剂， 反应 77.92h， 生成 <3S-(3α,4β,5β)>-3-(acetylamino)-3,4-dihydro-4-hydroxy-5-(hydroxymethyl)-2(5H)-furanone
  参考文献：
  名称：

  A convenient synthesis of polyoxamic acid, 5-O-carbamoylpolyoxamic acid, and their unnatural D isomers

  摘要：

  DOI：

  10.1021/jo00375a057

文献信息

• Synthesis of (+)-polyoxamic acid and D-sorbitol from simple achiral allylic halides employing (S,S)-hydrobenzoin as a chiral source
  作者：Kwan Soo Kim、Yong Joo Lee、Jin Hwan Kim、Da Kyung Sung

  DOI：10.1039/b202823a

  日期：2002.5.9

  S)-hydrobenzoin stannylene acetal followed by regio- and stereoselective transformations of the resulting allylic ether gave (+)-polyoxamic acid and a similar procedure was applied to the synthesis of D-sorbitol from trans-1-iodo-2-hexene.

  顺式-1-溴-2-戊烯与（S，S）-氢苯偶姻亚锡缩醛的偶合反应，然后对所得烯丙基醚进行区域和立体选择性转化，得到（+）-聚草酰胺酸，并采用相似的方法合成来自反式-1-碘-2-己烯的D-山梨醇。
• Asymmetric α-amino acid synthesis: synthesis of (+)-polyoxamic acid using a [3,3]allylic trifluoroacetimidate rearrangement
  作者：Ian Savage、Eric J. Thomas

  DOI：10.1039/c39890000717

  日期：——

  The stereoselective [3,3] rearrangement of allylic trifluoroacetimidate (15) has been used in a synthesis of (+)-polyoxamic acid (1).

  烯丙基三氟乙酰亚氨酸酯（15）的立体选择性[3,3]重排已用于（+）-聚草酰胺酸（1）的合成中。
• Stereoselective synthesis of allylic amines by rearrangement of allylic trifluoroacetimidates: stereoselective synthesis of polyoxamic acid and derivatives of other α-amino acids
  作者：Ian Savage、Eric J. Thomas、Peter D. Wilson

  DOI：10.1039/a905772b

  日期：——

  On heating in xylene under reflux, allylic trifluoroacetimidates undergo [3,3] sigmatropic rearrangement to regioisomeric allylic trifluoroacetamides. Examples include the rearrangements of the trifluoroacetimidates 16 and 73 to the trifluoroacetamides 17 and 74, which were incorporated into stereoselective syntheses of polyoxamic acid 1, and the rearrangement of the trifluoroacetimidate 26. The rearrangement was the key step in asymmetric syntheses of the (S)- and (R)-valine derivatives 37 and 48. Other examples include rearrangements of the trifluoroacetimidates 52, 54 and 56 prepared from geraniol, cinnamyl alcohol and sorbyl alcohol, respectively, and the more complex trifluoroacetimidates 62 and 69. The stereoselectivity of these rearrangements, which are somewhat faster than rearrangements of analogous allylic trichloroacetimidates, is consistent with the participation of chair-like, six-membered, transition structures.

  在甲苯中回流加热时，烯丙基三氟乙亚胺酸酯会发生[3,3] σ迁移重排，生成区域异构的烯丙基三氟乙酰胺。例如，三氟乙亚胺酸酯16和73重排生成三氟乙酰胺17和74，这些被用于合成聚氧基酸1的选择性合成中，以及三氟乙亚胺酸酯26的重排。这一重排是对映选择性合成(S)-和(R)-缬氨酸类似物37和48的关键步骤。其他例子包括由香叶醇、肉桂醇和苏儿醇分别制备的三氟乙亚胺酸酯52、54和56的重排，以及更复杂的三氟乙亚胺酸酯62和69的重排。这些重排的立体选择性比类似的烯丙基三氯乙亚胺酸酯重排稍快，与椅式六元过渡态结构的参与相符。
• An efficient and flexible route to (+)-polyoxamic acid using diastereoselective epoxidation of 1-arylthio-1-nitroalkenes
  作者：Richard F. W. Jackson、Nicholas J. Palmer、Martin J. Wythes

  DOI：10.1039/c39940000095

  日期：——

  Polyoxamic acid 4a is prepared by a short and efficient process in which the key steps are the highly diastereoselective nucleophilic epoxidation of the D-threitol-derived alkene 6 using potassium tert-butylperoxide, followed by reaction of the oxirane 7a with ammonia.

  聚氧肟酸4a是通过一个简短而有效的过程制备的，其中关键步骤是使用叔丁基过氧化钾对D-苏糖醇衍生的烯烃6进行高度立体选择性亲核环氧化，然后使环氧乙烷7a与氨反应。
• Asymmetric amidation of (2S,3S)-pent-4-ene-1,2,3-triol. Total syntheses of (–)-anisomycin and (+)-polyoxamic acid
  作者：Sung Ho Kang、Hyeong-Wook Choi

  DOI：10.1039/cc9960001521

  日期：——

  Intramolecular iodoamidation of pentenetriol 2 provides trihydroxy carbamate 8 in 94% de and was elaborated to (-)-anisomycin 15 and (+)-polyoxamic acid 19.