(3S,4S)-3-<(S)-1-hydroxyethyl>-1-p-methoxyphenyl-4-styrylazetidin-2-one | 101977-77-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: (3S,4S)-3-<(S)-1-hydroxyethyl>-1-p-methoxyphenyl-4-styrylazetidin-2-one
• 英文别名: <3S,4S(E)>-3-<1(S)-hydroxyethyl>-1-(4-methoxyphenyl)-4-(2-phenylethenyl)-2-azetidinone；(3S,4S(E))-3-(1(S)-hydroxyethyl)-1-(4-methoxyphenyl)-4-(2-phenylethenyl)-2-azetidinone；(3S,4S)-3-[(1S)-1-hydroxyethyl]-1-(4-methoxyphenyl)-4-[(E)-2-phenylethenyl]azetidin-2-one
• CAS: 101977-77-9
• 化学式: C₂₀H₂₁NO₃
• 分子量: 323.392
• InChiKey: KBUSDCKWQJQODQ-ZXVGVRINSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3S,4S)-3-<(S)-1-hydroxyethyl>-1-p-methoxyphenyl-4-styrylazetidin-2-one 在 sodium hydroxide 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 3.0h， 生成 <3S,4S(E)>-3-<1(R)-hydroxyethyl>-1-(4-methoxyphenyl)-4-(2-phenylethenyl)-2-azetidinone
  参考文献：
  名称：

  C-Aryl glycosides: electrophile-initiated cyclizations of 6-aryl-5-hexen-2-ols

  摘要：

  An approach to the synthesis of C-aryl glycosides is described. Treatment of beta-lactam 9 with N-bromosuccinimide (NBS) or N-iodosuccinimide (NIS) afforded trans-2,6-disubstituted pyrans 11a and 11b. Treatment of 9 with phenylselenenyl chloride (PhSeCl) or N-(phenylselenenyl)phthalimide (N-PSP) gave 11c and cis-2,6-disubstituted pyran 12c in different ratios depending on the reaction conditions. Treatment of beta-lactam 10 with NBS, NIS, PhSeCl, or N-PSP gave mixtures of pyrans 16 and 17. Treatment of unsaturated alcohol 24a with PhSeCl gave pyran 23a. Conversion of 23a to virenose analog 22, a C-aryl glycoside related to the chrysomycins, was accomplished using a selenoxide elimination-osmium tetraoxide oxidation sequence.

  DOI：

  10.1021/jo00047a020
• 作为产物：
  描述：

  (S)-3-羟基丁酸乙酯 、 N-(4-Methoxyphenyl)-3-phenylpropenaldimine 以25%的产率得到
  参考文献：
  名称：

  GALLUCCI, JUDITH C.;HA, DEOK-CHAN;HART, DAVID J., TETRAHEDRON, 45,(1989) N, C. 1283-1292

  摘要：

  DOI：

文献信息

• Preparation of aminosaccharides using ester-imine condensations: syntheses of methyl -benzoylacosaminide and methyl -[oxo(phenylmethoxy) acetyl)daunosaminide from (S)-ethyl 3-hydroxybutyrate
  作者：Judith C. Gallucci、Deok-Chan Ha、David J. Hart

  DOI：10.1016/0040-4020(89)80126-7

  日期：1989.1

  The dianion of (S)-ethyl β-hydroxybutyrate (1) was treated with -trimethylsilyl Imine 2 to afford β-lactam 4. The same dianion reacted with -ary1 imine 10 to give β-lactams 11, 12, and 13. A three-step sequence was used to convert 4 into the β-lactam-pyran hybrid 9 while a five-step sequence was developed to transform 11 and 12 into 9. Application of the carboxyinversion reaction to derivatives of

  将（S）-β-羟基丁酸乙酯（1）的二价阴离子用-三甲基甲硅烷基亚胺2处理，得到β-内酰胺4。相同的二价阴离子与-ary1亚胺10反应得到β-内酰胺11、12和13。使用三步序列将4转化为β-内酰胺-吡喃杂化物9，同时开发了五步序列将11和12转化为9。将羧基转化反应应用于9的衍生物，可得到氨基-保护的类似物糖蜜（5）和二十二胺（6）。
• An enantioselective approach to carbapenem antibiotics: formal synthesis of (+)-thienamycin
  作者：David J. Hart、Deok-Chan Ha

  DOI：10.1016/s0040-4039(01)80868-6

  日期：1985.1

  An enantioselective synthesis of intermediates in syntheses of thienamycin (15) and epithienamycin-C (16) is described.

  描述了在噻吩霉素（15）和上皮霉素-C（16）的合成中中间体的对映选择性合成。
• Cainelli, Gianfranco; Panunzio, Mauro; Basile, Tiziana, Journal of the Chemical Society. Perkin transactions I, 1987, p. 2637 - 2642
  作者：Cainelli, Gianfranco、Panunzio, Mauro、Basile, Tiziana、Bongini, Alessandro、Giacomini, Daria、Martelli, Giorgio

  DOI：——

  日期：——
• YOSHIOKA, TAKEO;CHIDA, NORITAKA;WATANABE, AZUMA;FUKAGAWA, YASUO;ISHIKARA,+
  作者：YOSHIOKA, TAKEO、CHIDA, NORITAKA、WATANABE, AZUMA、FUKAGAWA, YASUO、ISHIKARA,+

  DOI：——

  日期：——
• HATANAKA, MINORU;PARK, OEE-SOOK;UEDA, IKUO, TETRAHEDRON LETT., 31,(1990) N2, C. 7631-7632
  作者：HATANAKA, MINORU、PARK, OEE-SOOK、UEDA, IKUO

  DOI：——

  日期：——