(2S,3S,5R)-2-(phenylmethyl)-1-carbomethoxy-5-nonyl-3-pyrrolidinol | 131013-30-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (2S,3S,5R)-2-(phenylmethyl)-1-carbomethoxy-5-nonyl-3-pyrrolidinol
• 英文别名: (2S,3S,5R)-2-benzyl-3-hydroxy-1-methoxycarbonyl-5-nonylazolidine；(2S,3S,5R)-N-Methoxycarbonyl-2-benzyl-5-nonyl-3-pyrrolidinol；methyl (2S,3S,5R)-2-benzyl-3-hydroxy-5-nonylpyrrolidine-1-carboxylate
• CAS: 131013-30-4
• 化学式: C₂₂H₃₅NO₃
• 分子量: 361.525
• InChiKey: SERDRYDDZMIFSE-HKBOAZHASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  26
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.68
• 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：

  (2S,3S,5R)-2-(phenylmethyl)-1-carbomethoxy-5-nonyl-3-pyrrolidinol 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 2.5h， 以91%的产率得到1-甲基-2beta-苄基-5beta-壬基吡咯烷-3beta-醇
  参考文献：
  名称：

  Unprecedented Facial Diastereoselectivity in the Paternò-Büchi Reaction of a Chiral Dihydropyrrole—A Short Total Synthesis of (+)-Preussin

  摘要：

  DOI：

  10.1002/(sici)1521-3773(19981231)37:24<3400::aid-anie3400>3.0.co;2-3
• 作为产物：
  描述：

  Z-L-苯丙氨醇 在 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 palladium on activated charcoal 、 bis(acetylacetonate)oxovanadium 叔丁基过氧化氢 、 sodium hypochlorite 、 正丁基锂 、 氢气 、 四氯化锡 、 碳酸氢钠 、 sodium bromide 作用下， 以 四氢呋喃 、 甲醇 、 六甲基磷酰三胺 、 二氯甲烷 、 水 、 乙酸乙酯 、 甲苯 为溶剂， 反应 8.0h， 生成 (2S,3S,5R)-2-(phenylmethyl)-1-carbomethoxy-5-nonyl-3-pyrrolidinol
  参考文献：
  名称：

  Efficient Stereoselective Synthesis of (2S,3S,5R)-(+)-Preussin

  摘要：

  DOI：

  10.3987/com-00-s(i)69

文献信息

• The Synthesis of (+)-Preussin and Related Pyrrolidinols by Diastereoselective Paternò-Büchi Reactions of Chiral 2-Substituted 2,3-Dihydropyrroles
  作者：Thorsten Bach、Harm Brummerhop、Klaus Harms

  DOI：10.1002/1521-3765(20001016)6:20<3838::aid-chem3838>3.0.co;2-1

  日期：2000.10.16

  The N-alkoxycarbonyl substituted 2,3-dihydropyrroles 3 and 8 are converted to 2-benzyl-3-pyrrolidinols by the Paterno-Buchi reaction followed by hydrogenolysis. Since the addition of the photoexcited benzaldehyde at the unsaturated heterocycle proceeds in a syn fashion, the benzyl group at C-2 and the hydroxy group at C-3 of the product are cis oriented. The simple and facial diastereoselectivities of the Paterno-Buchi reaction were studied more closely and the relative configuration of the products was elucidated. The thermodynamically less stable endo product is formed as a result of simple diastereoselection. The face differentiation in 2-substituted 2,3-dihydropyrroles is presumably due to the nonplanarity of these heterocycles, which forces attack of the carbonyl group on the face with the existing substituent. All-cis-pyrrolidinols are consequently formed after hydrogenolysis. Following this route, a total synthesis of the pyrrolidinol alkaloid (+)-preussin (1) was conducted, which yielded the target compound in a total yield of 11% over nine steps starting from L-pyroglutaminol (11).
• Unprecedented Facial Diastereoselectivity in the Paternò-Büchi Reaction of a Chiral Dihydropyrrole—A Short Total Synthesis of (+)-Preussin
  作者：Thorsten Bach、Harm Brummerhop

  DOI：10.1002/(sici)1521-3773(19981231)37:24<3400::aid-anie3400>3.0.co;2-3

  日期：1998.12.31
• Total synthesis of (+)-preussin, a novel antifungal agent
  作者：Chwang Siek Pak、Ge Hyeong Lee

  DOI：10.1021/jo00003a040

  日期：1991.2

  The total synthesis of (+)-preussin, (2S,3S,5R)-1-methyl-5-nonyl-2-(phenylmethyl)-3-pyrrolidinol, was achieved by using D-glucose as the starting material. The key synthetic steps involved the sequential reduction and cyclization of azido triflate 6 to construct the pyrrolidine moiety 7 with the proper stereochemistry.
• PAK, CHWANG SIEK;LEE, GE HYEONG, J. ORG. CHEM., 56,(1991) N, C. 1128-1133
  作者：PAK, CHWANG SIEK、LEE, GE HYEONG

  DOI：——

  日期：——
• Efficient Stereoselective Synthesis of (2S,3S,5R)-(+)-Preussin
  作者：Janusz Jurczak、Antoni Krasinski、Henryk Gruza

  DOI：10.3987/com-00-s(i)69

  日期：——