2-trimethylsilylethyl (4aR,6R,7R,8S,8aR)-7-hydroxy-3-[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-oxo-3-phenylmethoxypropyl]-8-tri(propan-2-yl)silyloxy-6-[tri(propan-2-yl)silyloxymethyl]-6,7,8,8a-tetrahydro-4aH-pyrano[2,3-b][1,4]oxathiine-2-carboxylate | 766514-63-0

• 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: 2-trimethylsilylethyl (4aR,6R,7R,8S,8aR)-7-hydroxy-3-[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-oxo-3-phenylmethoxypropyl]-8-tri(propan-2-yl)silyloxy-6-[tri(propan-2-yl)silyloxymethyl]-6,7,8,8a-tetrahydro-4aH-pyrano[2,3-b][1,4]oxathiine-2-carboxylate
• CAS: 766514-63-0
• 化学式: C₄₇H₈₃NO₁₁SSi₃
• 分子量: 954.499
• InChiKey: MYRYZPVXGRPUCB-ZZRMRHNYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.08
• 重原子数：
  63
• 可旋转键数：
  25
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  173
• 氢给体数：
  2
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  2-trimethylsilylethyl (4aR,6R,7R,8S,8aR)-7-hydroxy-3-[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-oxo-3-phenylmethoxypropyl]-8-tri(propan-2-yl)silyloxy-6-[tri(propan-2-yl)silyloxymethyl]-6,7,8,8a-tetrahydro-4aH-pyrano[2,3-b][1,4]oxathiine-2-carboxylate 在 三甲基氯硅烷 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.5h， 生成 (4aR,6R,7R,8S,8aR)-3-[(S)-2-Benzyloxycarbonyl-2-(2-naphthalen-2-yl-acetylamino)-ethyl]-7-hydroxy-6-hydroxymethyl-8-triisopropylsilanyloxy-6,7,8,8a-tetrahydro-4aH-4,5-dioxa-1-thia-naphthalene-2-carboxylic acid 2-trimethylsilanyl-ethyl ester
  参考文献：
  名称：

  A New Scaffold for the Stereoselective Synthesis of α-O-Linked Glycopeptide Mimetics

  摘要：

  alpha-O-Linked glycohomoglutamates are obtained as diastereomerically pure compounds by chemo-, regio-, and stereoselective cycloadditions between glycals and aspartic acid derivatives. The latter constitute orthogonally functionalized scaffolds for glycopeptide mimetics.

  DOI：

  10.1021/jo049441h
• 作为产物：
  描述：

  (S)-2-tert-Butoxycarbonylamino-4-(2,2-dimethyl-4,6-dioxo-[1,3]dioxan-5-ylidene)-4-hydroxy-butyric acid benzyl ester 在 吡啶 、 phthalimidesulfenyl chloride 作用下， 以 氯仿 、 苯 为溶剂， 反应 40.0h， 生成 2-trimethylsilylethyl (4aR,6R,7R,8S,8aR)-7-hydroxy-3-[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-oxo-3-phenylmethoxypropyl]-8-tri(propan-2-yl)silyloxy-6-[tri(propan-2-yl)silyloxymethyl]-6,7,8,8a-tetrahydro-4aH-pyrano[2,3-b][1,4]oxathiine-2-carboxylate
  参考文献：
  名称：

  A New Scaffold for the Stereoselective Synthesis of α-O-Linked Glycopeptide Mimetics

  摘要：

  alpha-O-Linked glycohomoglutamates are obtained as diastereomerically pure compounds by chemo-, regio-, and stereoselective cycloadditions between glycals and aspartic acid derivatives. The latter constitute orthogonally functionalized scaffolds for glycopeptide mimetics.

  DOI：

  10.1021/jo049441h

文献信息

• A New Scaffold for the Stereoselective Synthesis of α-<i>O</i>-Linked Glycopeptide Mimetics
  作者：Francesca Venturi、Chiara Venturi、Francesca Liguori、Martina Cacciarini、Monica Montalbano、Cristina Nativi

  DOI：10.1021/jo049441h

  日期：2004.9.1

  alpha-O-Linked glycohomoglutamates are obtained as diastereomerically pure compounds by chemo-, regio-, and stereoselective cycloadditions between glycals and aspartic acid derivatives. The latter constitute orthogonally functionalized scaffolds for glycopeptide mimetics.