(1S,2R,4S)-2,2-dimethyl-4-(3-vinyloxiranyl)oxazolidine-3-carboxylic acid tert-butyl ester | 215728-69-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (1S,2R,4S)-2,2-dimethyl-4-(3-vinyloxiranyl)oxazolidine-3-carboxylic acid tert-butyl ester
• 英文别名: tert-butyl (4S)-4-[(2S,3R)-3-ethenyloxiran-2-yl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate
• CAS: 215728-69-1
• 化学式: C₁₄H₂₃NO₄
• 分子量: 269.341
• InChiKey: YSBOSYQQEKJJKJ-AXFHLTTASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  51.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  溴代十二烷 、 (1S,2R,4S)-2,2-dimethyl-4-(3-vinyloxiranyl)oxazolidine-3-carboxylic acid tert-butyl ester 在 叔丁基锂 作用下， 生成 (2S,3R,4E)-3-(tert-butoxycarbonyl)-4-(1-hydroxy-hexadec-2-enyl)-2,2-dimethyloxazolidine
  参考文献：
  名称：

  Asymmetric α-Chloroallylboration of Amino Aldehydes:  A Novel and Highly Versatile Route to d- and l-erythro-Sphingoid Bases

  摘要：

  Serinal-derived vinyloxiranes represent versatile building blocks for synthesis of D-(or L-)erythrosphingosine and, its analogues. Asymmetric alpha-chloroallylation of the Garner aldehyde with chiral and achiral gamma-(Z)-chloroallylboranes, followed by DBU-mediated cyclization of the corresponding chlorohydrins, provides a highly effective route to oxazolidine vinyloxiranes in high yield under mild conditions, Matched and mismatched cases of the double diastereoselective allylation were investigated. The vinyloxirane reacts with a variety of organocuprates by a S(N)2' type nucleophilic substitution, yielding protected sphingoid bases as (E)-allylic alcohols exclusively. By the new approach, a multitude of different; sphingoid core structures becomes available, from a uniform protocol, with high yield and efficiency.

  DOI：

  10.1021/jo990117+
• 作为产物：
  描述：

  3-反-溴碳-2,2'-二甲基氧酸酯 在 8-羟基喹啉 、 三氟化硼乙醚 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 (+)-B-methoxydiisocamphenylborane 作用下， 以 二氯甲烷 为溶剂， 生成 (1S,2R,4S)-2,2-dimethyl-4-(3-vinyloxiranyl)oxazolidine-3-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Serinal-derived vinyl oxiranes as novel and versatile building blocks for the stereoselective synthesis of D- and L-erythro-sphingosines

  摘要：

  噁唑烷乙烯基环氧乙烷 1 是一种用于制备对映体纯 D-(+)-赤藓-鞘氨醇及其类似物的新型多功能结构单元，它是通过对加纳醛进行氯烯丙基硼化而制备的，具有绝对的立体可控性和良好的收率。

  DOI：

  10.1039/a804415e

文献信息

• (6R,7R)-[4,5,6,7-2H4]-Palmitoate and (8S,9R)-[8,9-2H2]-l-erythro-Sphinganine: Probes for the Analysis of the Stereochemical Course of Δ6-Desaturases from Plants and Insects
  作者：Oliver Thum

  DOI：10.1055/s-1999-3630

  日期：1999.12
• Serinal-derived vinyl oxiranes as novel and versatile building blocks for the stereoselective synthesis of D- and L-erythro-sphingosines
  作者：Christian Hertweck、Wilhelm Boland、Helmar Goerls

  DOI：10.1039/a804415e

  日期：——

  Oxazolidine vinyl oxirane 1, a novel and highly versatile building block for the preparation of enantiopure D-(+)-erythro-sphingosine and analogues, has been prepared by chloroallylboration of the Garner aldehyde with absolute stereocontrol and in good yield.

  噁唑烷乙烯基环氧乙烷 1 是一种用于制备对映体纯 D-(+)-赤藓-鞘氨醇及其类似物的新型多功能结构单元，它是通过对加纳醛进行氯烯丙基硼化而制备的，具有绝对的立体可控性和良好的收率。
• Asymmetric α-Chloroallylboration of Amino Aldehydes:  A Novel and Highly Versatile Route to <scp>d</scp>- and <scp>l</scp>-<i>erythro</i>-Sphingoid Bases
  作者：Christian Hertweck、Wilhelm Boland

  DOI：10.1021/jo990117+

  日期：1999.6.1

  Serinal-derived vinyloxiranes represent versatile building blocks for synthesis of D-(or L-)erythrosphingosine and, its analogues. Asymmetric alpha-chloroallylation of the Garner aldehyde with chiral and achiral gamma-(Z)-chloroallylboranes, followed by DBU-mediated cyclization of the corresponding chlorohydrins, provides a highly effective route to oxazolidine vinyloxiranes in high yield under mild conditions, Matched and mismatched cases of the double diastereoselective allylation were investigated. The vinyloxirane reacts with a variety of organocuprates by a S(N)2' type nucleophilic substitution, yielding protected sphingoid bases as (E)-allylic alcohols exclusively. By the new approach, a multitude of different; sphingoid core structures becomes available, from a uniform protocol, with high yield and efficiency.