1-O-2-S-[1'-benzyloxycarbonyl-2'-(4'-t-butoxycarbonylamino)-methylpropionate-1'-2'-ethenyl]-3,4,6-tri-O-benzyl-α-D-glucopyranoside | 766514-49-2

• 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: 1-O-2-S-[1'-benzyloxycarbonyl-2'-(4'-t-butoxycarbonylamino)-methylpropionate-1'-2'-ethenyl]-3,4,6-tri-O-benzyl-α-D-glucopyranoside
• 英文别名: methyl (4aR,6R,7R,8S,8aR)-3-[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-oxo-3-phenylmethoxypropyl]-7,8-bis(phenylmethoxy)-6-(phenylmethoxymethyl)-6,7,8,8a-tetrahydro-4aH-pyrano[2,3-b][1,4]oxathiine-2-carboxylate
• CAS: 766514-49-2
• 化学式: C₄₆H₅₁NO₁₁S
• 分子量: 825.977
• InChiKey: LCKPCMNLTDVINO-UHKKDHQASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  59
• 可旋转键数：
  21
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  162
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  1-O-2-S-[1'-benzyloxycarbonyl-2'-(4'-t-butoxycarbonylamino)-methylpropionate-1'-2'-ethenyl]-3,4,6-tri-O-benzyl-α-D-glucopyranoside 在 三氟甲磺酸三甲基硅酯 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 4.5h， 生成 methyl (4aR,6R,7R,8S,8aR)-3-[(2S)-2-acetamido-3-methoxy-3-oxopropyl]-6-(hydroxymethyl)-7,8-bis(phenylmethoxy)-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
• 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 25.0h， 生成 1-O-2-S-[1'-benzyloxycarbonyl-2'-(4'-t-butoxycarbonylamino)-methylpropionate-1'-2'-ethenyl]-3,4,6-tri-O-benzyl-α-D-glucopyranoside
  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.