tert-butyl (2S)-2-[[(Z,7S,8R,9S)-9-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-7,8,9-tris(phenylmethoxy)non-5-enoyl]amino]-3-methylbutanoate | 910630-77-2

• 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: tert-butyl (2S)-2-[[(Z,7S,8R,9S)-9-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-7,8,9-tris(phenylmethoxy)non-5-enoyl]amino]-3-methylbutanoate
• CAS: 910630-77-2
• 化学式: C₄₄H₅₉NO₈
• 分子量: 729.954
• InChiKey: YDVJUQVSJDJWIO-WMCWVGRJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  53
• 可旋转键数：
  22
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  102
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  tert-butyl (2S)-2-[[(Z,7S,8R,9S)-9-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-7,8,9-tris(phenylmethoxy)non-5-enoyl]amino]-3-methylbutanoate 在 四氧化锇 、 N-甲基吲哚酮 、 三氟甲磺酸 、 水 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 环己烷 为溶剂， 反应 4.0h， 生成 (S)-3-Methyl-2-[(5S,6S,7S,8S,9S)-5,6,7,8,9-pentakis-benzyloxy-9-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-nonanoylamino]-butyric acid tert-butyl ester
  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 、 碳酸氢钠 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 戴斯-马丁氧化剂 、 (+)-10-camphorsulfonic acid 、 N,N-二异丙基乙胺 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 16.0h， 生成 tert-butyl (2S)-2-[[(Z,7S,8R,9S)-9-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-7,8,9-tris(phenylmethoxy)non-5-enoyl]amino]-3-methylbutanoate
  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.