methyl 4,6-O-benzylidene-2-deoxy-2-dimethylmaleimido-β-D-glucopyranose | 1000403-62-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: methyl 4,6-O-benzylidene-2-deoxy-2-dimethylmaleimido-β-D-glucopyranose
• 英文别名: 1-[(4aR,6R,7R,8R,8aS)-8-hydroxy-6-methoxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-yl]-3,4-dimethylpyrrole-2,5-dione
• CAS: 1000403-62-2
• 化学式: C₂₀H₂₃NO₇
• 分子量: 389.405
• InChiKey: JJFVHTLLMCZEOU-ZLKCUPGUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  94.5
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl 4,6-O-benzylidene-2-deoxy-2-dimethylmaleimido-β-D-glucopyranose 在 吡啶 、 三氟甲磺酸 、 硼烷-三甲胺络合物 、 4 A molecular sieve 、 三氟化硼乙醚 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 3.0h， 生成 methyl 3-O-acetyl-6-O-benzyl-2-deoxy-2-dimethylmaleimido-β-D-glucopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido-β-D-glucopyranosyl-(1->4)-3-O-acetyl-6-O-benzyl-2-deoxy-2-dimethylmaleimido-β-D-glucopyranoside
  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：

  methyl 3,4,6-tri-O-acetyl-2-deoxy-2-dimethylmaleimido-β-D-glucopyranoside 在 sodium methylate 、 对甲苯磺酸 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 2.5h， 生成 methyl 4,6-O-benzylidene-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

文献信息

• Differential O-3/O-4 regioselectivity in the glycosylation of α and β anomers of 6-O-substituted N-dimethylmaleoyl-protected d-glucosamine acceptors
  作者：María L. Bohn、María I. Colombo、Pablo L. Pisano、Carlos A. Stortz、Edmundo A. Rúveda

  DOI：10.1016/j.carres.2007.08.006

  日期：2007.12

  An assessment of the relative O-3/O-4 reactivities of both methyl alpha- and beta-D-glycosides of N-dimethylmaleoyl (DMM) D-glucosamine acceptors protected at O-6 with benzoyl (Bz), benzyl (Bn), and tert-butyldiphenylsilyl (TBDPS) groups is presented using per-O-benzoylated beta-D-galactofuranosyl and per-O-acetylated alpha-D-galactopyranosyl trichloroacetimidates as glycosyl donors. Using the former donor, the a anomer of the 6-O-benzoylated compound gave exclusive substitution at O-3, whereas the other two compounds with a-configuration kept this site as preferential. The P anomer of the 6-O-benzoylated compound gave the same amounts of reaction products on O-3 and O-4, whereas the other P analogs carried a more reactive O-4. The same reactions were carried out using as donor the less-reactive per-O-acetylated alpha-D-galactopyranosyl trichloroacetimidate. Although the same trend was found to occur, the O-4 was always relatively more reactive with the pyranosyl donor than with the furanosyl donor, when keeping the remaining factors constant. Furthermore, the P anomers of the acceptor gave almost exclusive substitution at O-4. These observations confirm and extend the utility of these 'matching' donor and acceptor reactivities. (c) 2007 Elsevier Ltd. All rights reserved.
• 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.