tri(propan-2-yl)silyl (17R,18S,19S,20S,21S,22S)-17-hydroxy-26-[[(2S)-3-methyl-1-[(2-methylpropan-2-yl)oxy]-1-oxobutan-2-yl]amino]-26-oxo-18,19,20,21,22-pentakis(phenylmethoxy)hexacos-14-ynoate | 910630-80-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: tri(propan-2-yl)silyl (17R,18S,19S,20S,21S,22S)-17-hydroxy-26-[[(2S)-3-methyl-1-[(2-methylpropan-2-yl)oxy]-1-oxobutan-2-yl]amino]-26-oxo-18,19,20,21,22-pentakis(phenylmethoxy)hexacos-14-ynoate
• CAS: 910630-80-7
• 化学式: C₇₉H₁₁₃NO₁₁Si
• 分子量: 1280.85
• InChiKey: XILLVBXMYAZOLB-IINRIZEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  17.72
• 重原子数：
  92
• 可旋转键数：
  47
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  148
• 氢给体数：
  2
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  tri(propan-2-yl)silyl (17R,18S,19S,20S,21S,22S)-17-hydroxy-26-[[(2S)-3-methyl-1-[(2-methylpropan-2-yl)oxy]-1-oxobutan-2-yl]amino]-26-oxo-18,19,20,21,22-pentakis(phenylmethoxy)hexacos-14-ynoate 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 0.17h， 生成 (17R,18S,19S,20S,21S,22S)-18,19,20,21,22-Pentakis-benzyloxy-25-((S)-1-tert-butoxycarbonyl-2-methyl-propylcarbamoyl)-17-hydroxy-pentacos-14-ynoic acid
  参考文献：
  名称：

  Stereochemistry of Sagittamide A:  Prediction and Confirmation

  摘要：

  The C5-C10 relative stereochemistry of sagittamide A was predicted, with the use of the (3)J(H,H) profiles assembled from the spin-coupling constants reported in the literature. The predicted relative stereochemistry was then confirmed by a total synthesis of two relevant remote diastereomers. The absolute configuration of sagittamide A was established through a detailed H-1 NMR analysis of the two remote diastereomers, followed by doping experiments of them with the authentic natural product.

  DOI：

  10.1021/ol061582d
• 作为产物：
  描述：

  2,3,4-tri-O-benzyl-D-galactopyranoside 在 sodium tetrahydroborate 、 四氧化锇 、 正丁基锂 、 N-甲基吲哚酮 、 三氟甲磺酸 、 三氟化硼乙醚 、 水 、 碳酸氢钠 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 戴斯-马丁氧化剂 、 溶剂黄146 、 (+)-10-camphorsulfonic acid 、 N,N-二异丙基乙胺 、 三苯基膦 、 lithium hexamethyldisilazane 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醚 、 乙醇 、 二氯甲烷 、 氯仿 、 环己烷 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 32.5h， 生成 tri(propan-2-yl)silyl (17R,18S,19S,20S,21S,22S)-17-hydroxy-26-[[(2S)-3-methyl-1-[(2-methylpropan-2-yl)oxy]-1-oxobutan-2-yl]amino]-26-oxo-18,19,20,21,22-pentakis(phenylmethoxy)hexacos-14-ynoate
  参考文献：
  名称：

  Stereochemistry of Sagittamide A:  Prediction and Confirmation

  摘要：

  The C5-C10 relative stereochemistry of sagittamide A was predicted, with the use of the (3)J(H,H) profiles assembled from the spin-coupling constants reported in the literature. The predicted relative stereochemistry was then confirmed by a total synthesis of two relevant remote diastereomers. The absolute configuration of sagittamide A was established through a detailed H-1 NMR analysis of the two remote diastereomers, followed by doping experiments of them with the authentic natural product.

  DOI：

  10.1021/ol061582d

文献信息

• Stereochemistry of Sagittamide A:  Prediction and Confirmation
  作者：Hirofumi Seike、Indranath Ghosh、Yoshito Kishi

  DOI：10.1021/ol061582d

  日期：2006.8.1

  The C5-C10 relative stereochemistry of sagittamide A was predicted, with the use of the (3)J(H,H) profiles assembled from the spin-coupling constants reported in the literature. The predicted relative stereochemistry was then confirmed by a total synthesis of two relevant remote diastereomers. The absolute configuration of sagittamide A was established through a detailed H-1 NMR analysis of the two remote diastereomers, followed by doping experiments of them with the authentic natural product.