(2'R,3'R,4R,5S)-2,2-dimethyl-5-<(tert-butyldimethylsilyloxy)methyl>-4-<3'-<(4''-methylphenyl)thio>-3'-nitrooxiran-2'-yl>-1,3-dioxolane | 157661-83-1

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: (2'R,3'R,4R,5S)-2,2-dimethyl-5-<(tert-butyldimethylsilyloxy)methyl>-4-<3'-<(4''-methylphenyl)thio>-3'-nitrooxiran-2'-yl>-1,3-dioxolane
• 英文别名: tert-butyl-[[(4S,5R)-2,2-dimethyl-5-[(2R,3R)-3-(4-methylphenyl)sulfanyl-3-nitrooxiran-2-yl]-1,3-dioxolan-4-yl]methoxy]-dimethylsilane
• CAS: 157661-83-1
• 化学式: C₂₁H₃₃NO₆SSi
• 分子量: 455.648
• InChiKey: ARBBKVMGIJKARG-XKGFGPFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.96
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  111
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2'R,3'R,4R,5S)-2,2-dimethyl-5-<(tert-butyldimethylsilyloxy)methyl>-4-<3'-<(4''-methylphenyl)thio>-3'-nitrooxiran-2'-yl>-1,3-dioxolane 在 ammonium hydroxide 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 30.0h， 生成 <3S-(3α,4β,5β)>-3-(acetylamino)-3,4-dihydro-4-hydroxy-5-(hydroxymethyl)-2(5H)-furanone
  参考文献：
  名称：

  An efficient and flexible route to (+)-polyoxamic acid using diastereoselective epoxidation of 1-arylthio-1-nitroalkenes

  摘要：

  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。

  DOI：

  10.1039/c39940000095
• 作为产物：
  描述：

  (4R,5S)-5-tert-butyldimethylsilyloxymethyl-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde 在 potassium tert-butylate 、 potassium tert-butylperoxide 、 甲基磺酰氯 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 叔丁醇 为溶剂， 反应 7.0h， 生成 (2'R,3'R,4R,5S)-2,2-dimethyl-5-<(tert-butyldimethylsilyloxy)methyl>-4-<3'-<(4''-methylphenyl)thio>-3'-nitrooxiran-2'-yl>-1,3-dioxolane
  参考文献：
  名称：

  An efficient and flexible route to (+)-polyoxamic acid using diastereoselective epoxidation of 1-arylthio-1-nitroalkenes

  摘要：

  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。

  DOI：

  10.1039/c39940000095

文献信息

• 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。
• A New Approach to the Synthesis of .beta.-Hydroxy-.alpha.-amino Acids Using (Arylthio)nitrooxiranes
  作者：Richard F. W. Jackson、Nicholas J. Palmer、Martin J. Wythes、William Clegg、Mark R. J. Elsegood

  DOI：10.1021/jo00125a032

  日期：1995.10

  2-(Arylthio)-2-nitrooxiranes, prepared by the nucleophilic epoxidation of 1-(arylthio)-1-nitroalkenes using anhydrous metal alkyl peroxides in tetrahydrofuran, react with aqueous ammonia to give alpha-amino thioesters in good yield, without significant formation of the primary amide by subsequent reaction of the thioester with ammonia. lit situ protection of the amino group is possible, leading to a range of protected derivatives. Diastereoselective epoxidation of 1-(arylthio)-1-nitroalkenes with an allylic, oxygen-substituted stereogenic center using metal alkyl peroxides is possible, and the sense of diastereoselectivity can be controlled simply by use of lithium or potassium as the counterion. Enhanced syn selectivity (15:1) in lithium tert-butyl peroxide mediated epoxidations can be achieved by using toluene as solvent. Use of potassium triphenylmethyl peroxide, rather than potassium tert-butyl peroxide, generally gives higher anti selectivity (12:1). Reactions of enantiomerically and diastereoisomerically pure 2-(arylthio)-2-nitrooxiranes with ammonia proceed stereospecifically with inversion of configuration, establishing a stereocontrolled route to beta-hydroxy-alpha-amino acids. Use of other nitrogen nucleophiles, for example amino acid esters, is also possible, leading to a stereospecific approach to a-amino dicarboxylic acids. Applications of this methodology, which constitutes a stereocontrolled Strecker reaction, to the synthesis of gamma-hydroxy threonine derivatives 19-22, polyoxamic acid (26), and the C-5 epimer of the sugar fragment of polyoxin C (27) are described.