(S)-1-((1S,5R,7R)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-2-hydroxy-2-methoxy-ethanone | 178603-15-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (S)-1-((1S,5R,7R)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-2-hydroxy-2-methoxy-ethanone
• 英文别名: (2S)-1-[(1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3lambda6-thia-4-azatricyclo[5.2.1.01,5]decan-4-yl]-2-hydroxy-2-methoxyethanone；(2S)-1-[(1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ6-thia-4-azatricyclo[5.2.1.01,5]decan-4-yl]-2-hydroxy-2-methoxyethanone
• CAS: 178603-15-1
• 化学式: C₁₃H₂₁NO₅S
• 分子量: 303.379
• InChiKey: JTMSVAFVXBFFIR-MBJVOQIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  92.3
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-1-((1S,5R,7R)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-2-hydroxy-2-methoxy-ethanone 在 phosphate buffer 、 碘 、 zinc dibromide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 30.0h， 生成 (2R)-bornane-10,2-sultam
  参考文献：
  名称：

  Diastereoselective allylation of N-glyoxyloyl-(2R)-bornane-10,2-sultam and (1R)-8-phenylmenthyl glyoxylate: synthesis of (2S,4S)-2-hydroxy-4-hydroxymethyl-4-butanolide

  摘要：

  The diastereoselective addition of allylsilanes and allylstannanes to N-glyoxyloyl-(2R)-bornane-10,2-sultam 1 and (1R)-8-phenylmenthyl glyoxylate 7 in the presence of Lewis acids has been studied. We obtained diastereoselectivities up to 84% and 94% for the allylation of 2 and 7, respectively. The application of the allylation products of 1 or 2 in the synthesis of 4-butanolides, for example (2S,4S)-2-hydroxy-4-hydroxymethyl-4-butanolide 13 is presented. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.10.025
• 作为产物：
  描述：

  甲醇 、 (1S)-N-crotyl-2,10-camphorsultam 在 二甲基硫 、 臭氧 作用下， 生成 (S)-1-((1S,5R,7R)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-2-hydroxy-2-methoxy-ethanone
  参考文献：
  名称：

  Efficient synthesis of N-glyoxyloyl-(2R)-bornane-10,2-sultam

  摘要：

  Starting from (2R)-bornane-10,2-sultam 1, the useful chiron N-glyoxyloyl-(2R)-bornane-10,2-sultam 5 is prepared via its crystalline precursor 4. The hemiacetal 4 whose structure was proved by the X-ray analysis is formed in diastereomerically pure form. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00155-3

文献信息

• The asymmetric ene reaction of N-glyoxyloyl-(2R)-bornane-10,2-sultam with 1-pentene and 1-hexene
  作者：Artur Jeżewski、Katarzyna Chajewska、Zbigniew Wielogórski、Janusz Jurczak

  DOI：10.1016/s0957-4166(97)00130-4

  日期：1997.6

  The asymmetric ene reaction of N-glyoxyloyl-(2R)-bornane-10,2-sultarn 2 and its hemiacetal 3 with I-pentene 4 and I-hexene 5 in the presence of Lewis acids is reported. All the ene reactions studied led to diastereoisomeric mixtures of olefins 6 and 7 or 8 and 9, with predominance of products of the (S) absolute configuration on the newly formed stereogenic center. The absolute configuration (via X-ray analysis of 6 and chemical correlation) and the extent of asymmetric induction were established. Stereochemical models are proposed. (C) 1997 Elsevier Science Ltd.
• Synthesis of chiral 4-substituted 2-hydroxypent-4-enoic acid derivatives via diastereoselective ene reaction promoted by ZnBr2
  作者：Piotr Kwiatkowski、Jacek Kwiatkowski、Jakub Majer、Janusz Jurczak

  DOI：10.1016/j.tetasy.2007.01.007

  日期：2007.2

  The diastereoselective carbonyl-ene reaction of various 1,1-disubstituted olefins with the chiral derivatives of glyoxylic acid, with Oppolzer's sultam 1a and 8-phenylmenthol 1b auxiliaries, was studied. The reaction proceeds effectively under undemanding conditions in the presence of equimolar or catalytic amount of ZnBr2 in good yield and at 72-94% de. Diastereoselectivities are usually slightly better with 8-phenylmenthyl glyoxylate 1b, however, the use of hemiacetal la is preferred because the products are often crystalline. (c) 2007 Elsevier Ltd. All rights reserved.
• Diastereoselective Addition of Allyltrimethylsilane to<i>N</i>-Glyoxyloyl-(<i>2R</i>)-bornane-10,2-sultam. A new synthesis of (<i>S</i>)-1,2-Pentanediol
  作者：Katarzyna Kiegiel、Piotr Prokopowicz、Janusz Jurczak

  DOI：10.1080/00397919908085920

  日期：1999.11

  Addition of allyltrimethylsilane (3) to N-glyoxyloyl-(2R)-bornane-10,2-sultam (4) in the presence of Lewis acid afforded, in high diastereoselectivity, adduct (2'S)-6 which, after recrystallization, was hydrogenated to give optically pure (S)-1,2-pentanediol (1).
• Efficient synthesis of N-glyoxyloyl-(2R)-bornane-10,2-sultam
  作者：Tomasz Bauer、Artur Jeżewski、Christian Chapuis、Janusz Jurczak

  DOI：10.1016/0957-4166(96)00155-3

  日期：1996.5

  Starting from (2R)-bornane-10,2-sultam 1, the useful chiron N-glyoxyloyl-(2R)-bornane-10,2-sultam 5 is prepared via its crystalline precursor 4. The hemiacetal 4 whose structure was proved by the X-ray analysis is formed in diastereomerically pure form. Copyright (C) 1996 Elsevier Science Ltd
• Diastereoselective allylation of N-glyoxyloyl-(2R)-bornane-10,2-sultam and (1R)-8-phenylmenthyl glyoxylate: synthesis of (2S,4S)-2-hydroxy-4-hydroxymethyl-4-butanolide
  作者：Katarzyna Kiegiel、Tomasz Bałakier、Piotr Kwiatkowski、Janusz Jurczak

  DOI：10.1016/j.tetasy.2004.10.025

  日期：2004.12

  The diastereoselective addition of allylsilanes and allylstannanes to N-glyoxyloyl-(2R)-bornane-10,2-sultam 1 and (1R)-8-phenylmenthyl glyoxylate 7 in the presence of Lewis acids has been studied. We obtained diastereoselectivities up to 84% and 94% for the allylation of 2 and 7, respectively. The application of the allylation products of 1 or 2 in the synthesis of 4-butanolides, for example (2S,4S)-2-hydroxy-4-hydroxymethyl-4-butanolide 13 is presented. (C) 2004 Elsevier Ltd. All rights reserved.