(1R)-1-[(1S,2S,3R,4R)-3-[[tert-butyl(dimethyl)silyl]oxymethyl]-7-oxabicyclo[2.2.1]hept-5-en-2-yl]-1-hydroxyhexan-3-one | 198822-22-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R)-1-[(1S,2S,3R,4R)-3-[[tert-butyl(dimethyl)silyl]oxymethyl]-7-oxabicyclo[2.2.1]hept-5-en-2-yl]-1-hydroxyhexan-3-one
• CAS: 198822-22-9
• 化学式: C₁₉H₃₄O₄Si
• 分子量: 354.562
• InChiKey: UCZIQYDLLACPQS-DZVNLGKHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1R)-1-[(1S,2S,3R,4R)-3-[[tert-butyl(dimethyl)silyl]oxymethyl]-7-oxabicyclo[2.2.1]hept-5-en-2-yl]-1-hydroxyhexan-3-one 在 4 A molecular sieve 、 sodium cyanoborohydride 、 溶剂黄146 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 37.0h， 生成 (1S,2S,3R,4R,1'R,3'R)-2-(4'-benzyl-3'-propyl-4',6'-tetrahydrooxazinyl)-3-tert-butyldimethylsilyloxymethyl-7-oxabicyclo[2.2.1]hept-5-ene
  参考文献：
  名称：

  致力于Pamamycin-607的总合成：东部部分的制备（C 8 –C 18片段）

  摘要：

  Pamamycin-607属于一组由各种“链霉菌”生产的同源大环氧化物，它们具有显着的自调节抗真菌，抗菌和阴离子转移活性。此处报道了帕马霉素-607的非外消旋C 8 -C 18部分的合成，该方法的特征是立体选择性羟醛缩合，然后立体控制还原羟胺化胺化和分子内迈克尔形成顺式-选择性四氢呋喃。由底物的几何形状引起的环化。

  DOI：

  10.1002/(sici)1099-0690(199909)1999:9<2303::aid-ejoc2303>3.0.co;2-8
• 作为产物：
  描述：

  (1S,2S,3R,4R)-2-乙酰氧基甲基-3-羟甲基-7-氧杂双环[2.2.1]庚-5-烯 在 咪唑 、 氢氧化钾 、 戴斯-马丁氧化剂 、 lithium diisopropyl amide 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.5h， 生成 (1R)-1-[(1S,2S,3R,4R)-3-[[tert-butyl(dimethyl)silyl]oxymethyl]-7-oxabicyclo[2.2.1]hept-5-en-2-yl]-1-hydroxyhexan-3-one
  参考文献：
  名称：

  A novel and efficient stereoselective synthesis of the southern part of pamamycin-607

  摘要：

  The C1'C11' portion of the antibiotic pamamycin-607 Was synthesized from the enantiomerically pure hydroxy acetate 3, readily available by enzymatic transesterification of the corresponding diol with vinylacetate. This synthesis entailed a series of stereoselective transformations: the absolute configurations of C-6' and C-8' were fixed by an aldol condensation followed by an anti-reduction of the resulting beta-hydroxyketone. The configurations of the last two asymmetric centers C-2' and C-3' were controlled by a novel highly diastereoselective intramolecular cyclization catalyzed by fluoride ions. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00475-8

文献信息

• A novel and efficient stereoselective synthesis of the southern part of pamamycin-607
  作者：Gérard Mandville、Christian Girard、Robert Bloch

  DOI：10.1016/s0957-4166(97)00475-8

  日期：1997.11

  The C1'C11' portion of the antibiotic pamamycin-607 Was synthesized from the enantiomerically pure hydroxy acetate 3, readily available by enzymatic transesterification of the corresponding diol with vinylacetate. This synthesis entailed a series of stereoselective transformations: the absolute configurations of C-6' and C-8' were fixed by an aldol condensation followed by an anti-reduction of the resulting beta-hydroxyketone. The configurations of the last two asymmetric centers C-2' and C-3' were controlled by a novel highly diastereoselective intramolecular cyclization catalyzed by fluoride ions. (C) 1997 Elsevier Science Ltd.
• Towards the Total Synthesis of Pamamycin-607: Preparation of the Eastern Part (C8–C18 Fragment)
  作者：Gérard Mandville、Robert Bloch

  DOI：10.1002/(sici)1099-0690(199909)1999:9<2303::aid-ejoc2303>3.0.co;2-8

  日期：1999.9

  Pamamycin-607 belongs to a group of homologous macrodiolides, produced by various “Streptomyces”, that possess remarkable autoregulatory antifungal, antibacterial and anion-transfering activities. The synthesis of the non-racemic C8–C18 portion of pamamycin-607 is reported here and involves a route that features a stereoselective aldol condensation followed by a stereocontrolled reductive amination

  Pamamycin-607属于一组由各种“链霉菌”生产的同源大环氧化物，它们具有显着的自调节抗真菌，抗菌和阴离子转移活性。此处报道了帕马霉素-607的非外消旋C 8 -C 18部分的合成，该方法的特征是立体选择性羟醛缩合，然后立体控制还原羟胺化胺化和分子内迈克尔形成顺式-选择性四氢呋喃。由底物的几何形状引起的环化。