1-[(2R,4aR,6S,7R,8R,8aS)-6-[(2R,3S,4R,5R,6S)-6-[tert-butyl(dimethyl)silyl]oxy-5-(3,4-dimethyl-2,5-dioxopyrrol-1-yl)-4-phenylmethoxy-2-(phenylmethoxymethyl)oxan-3-yl]oxy-8-hydroxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-yl]-3,4-dimethylpyrrole-2,5-dione | 678159-13-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-[(2R,4aR,6S,7R,8R,8aS)-6-[(2R,3S,4R,5R,6S)-6-[tert-butyl(dimethyl)silyl]oxy-5-(3,4-dimethyl-2,5-dioxopyrrol-1-yl)-4-phenylmethoxy-2-(phenylmethoxymethyl)oxan-3-yl]oxy-8-hydroxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-yl]-3,4-dimethylpyrrole-2,5-dione
• CAS: 678159-13-2
• 化学式: C₅₁H₆₂N₂O₁₃Si
• 分子量: 939.144
• InChiKey: IJBLGBUZKWWEDU-QCNMWCNXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.27
• 重原子数：
  67
• 可旋转键数：
  15
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.49
• 拓扑面积：
  169
• 氢给体数：
  1
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  1-[(2R,4aR,6S,7R,8R,8aS)-6-[(2R,3S,4R,5R,6S)-6-[tert-butyl(dimethyl)silyl]oxy-5-(3,4-dimethyl-2,5-dioxopyrrol-1-yl)-4-phenylmethoxy-2-(phenylmethoxymethyl)oxan-3-yl]oxy-8-hydroxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-yl]-3,4-dimethylpyrrole-2,5-dione 在 吡啶 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 乙酸乙酯 为溶剂， 反应 4.0h， 生成 3-O-acetyl-4,6-O-benzylidene-2-deoxy-2-dimethylmaleimido-β-D-glucopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido-β-D-glucopyranose
  参考文献：
  名称：

  Synthesis of a Fragment of Bacterial Cell Wall

  摘要：

  Cell wall is indispensable for survival of bacteria. This large molecular "mesh" encases the entire cytoplasm of bacteria, and it is comprised of repeating backbone units of N-acetyl-glucosamine (NAG)-N-acetyl-muramic acid (NAM). A pentapeptide is attached to each of the lactyl units of the N-acetyl-muramic acid. The cell wall has both cross-linked and non-cross-linked components. In the present paper, we have devised a synthetic route for the preparation of a fragment of the cell wall comprised of a tetrasaccharide (NAG-NAM-NAG-NAM), along with the two appended peptides. We also report the syntheses of three glycosyl donors (compounds 5, 7, and 9) and three glycosyl acceptors (compounds 4, 6, and 8) based on the D-glucosamine structure as a building unit. The synthetic strategy that is disclosed is generally useful in construction of other natural products containing the D-glucosamine as a building block.

  DOI：

  10.1021/jo035583k
• 作为产物：
  描述：

  2,3-二甲基马来酸酐 在 咪唑 、 三氟甲磺酸 、 sodium methylate 、 乙酸肼 、 二正丁基氧化锡 、 对甲苯磺酸 作用下， 以 甲醇 、 二氯甲烷 、 环己烷 、 乙腈 为溶剂， 反应 6.0h， 生成 1-[(2R,4aR,6S,7R,8R,8aS)-6-[(2R,3S,4R,5R,6S)-6-[tert-butyl(dimethyl)silyl]oxy-5-(3,4-dimethyl-2,5-dioxopyrrol-1-yl)-4-phenylmethoxy-2-(phenylmethoxymethyl)oxan-3-yl]oxy-8-hydroxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-yl]-3,4-dimethylpyrrole-2,5-dione
  参考文献：
  名称：

  Synthesis of a Fragment of Bacterial Cell Wall

  摘要：

  Cell wall is indispensable for survival of bacteria. This large molecular "mesh" encases the entire cytoplasm of bacteria, and it is comprised of repeating backbone units of N-acetyl-glucosamine (NAG)-N-acetyl-muramic acid (NAM). A pentapeptide is attached to each of the lactyl units of the N-acetyl-muramic acid. The cell wall has both cross-linked and non-cross-linked components. In the present paper, we have devised a synthetic route for the preparation of a fragment of the cell wall comprised of a tetrasaccharide (NAG-NAM-NAG-NAM), along with the two appended peptides. We also report the syntheses of three glycosyl donors (compounds 5, 7, and 9) and three glycosyl acceptors (compounds 4, 6, and 8) based on the D-glucosamine structure as a building unit. The synthetic strategy that is disclosed is generally useful in construction of other natural products containing the D-glucosamine as a building block.

  DOI：

  10.1021/jo035583k

文献信息

• Synthesis of a Fragment of Bacterial Cell Wall
  作者：Dusan Hesek、Mijoon Lee、Ken-ichiro Morio、Shahriar Mobashery

  DOI：10.1021/jo035583k

  日期：2004.3.1

  Cell wall is indispensable for survival of bacteria. This large molecular "mesh" encases the entire cytoplasm of bacteria, and it is comprised of repeating backbone units of N-acetyl-glucosamine (NAG)-N-acetyl-muramic acid (NAM). A pentapeptide is attached to each of the lactyl units of the N-acetyl-muramic acid. The cell wall has both cross-linked and non-cross-linked components. In the present paper, we have devised a synthetic route for the preparation of a fragment of the cell wall comprised of a tetrasaccharide (NAG-NAM-NAG-NAM), along with the two appended peptides. We also report the syntheses of three glycosyl donors (compounds 5, 7, and 9) and three glycosyl acceptors (compounds 4, 6, and 8) based on the D-glucosamine structure as a building unit. The synthetic strategy that is disclosed is generally useful in construction of other natural products containing the D-glucosamine as a building block.