1-((2R,3R,4R,5S,6R)-4,5-Dihydroxy-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-3-yl)-3,4-dimethyl-pyrrole-2,5-dione | 898547-26-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-((2R,3R,4R,5S,6R)-4,5-Dihydroxy-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-3-yl)-3,4-dimethyl-pyrrole-2,5-dione
• CAS: 898547-26-7
• 化学式: C₁₃H₁₉NO₇
• 分子量: 301.296
• InChiKey: MORBCPNNXFBNPT-RGXSPZPFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.85
• 重原子数：
  21.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  116.53
• 氢给体数：
  3.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  1-((2R,3R,4R,5S,6R)-4,5-Dihydroxy-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-3-yl)-3,4-dimethyl-pyrrole-2,5-dione 在 吡啶 、 硼烷-三甲胺络合物 、 三氟化硼乙醚 、 对甲苯磺酸 作用下， 以 乙腈 为溶剂， 反应 3.5h， 生成 methyl 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：

  在 甲醇 、 碘代三甲硅烷 作用下， 以 二氯甲烷 为溶剂， 反应 0.66h， 生成 1-((2R,3R,4R,5S,6R)-4,5-Dihydroxy-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-3-yl)-3,4-dimethyl-pyrrole-2,5-dione
  参考文献：
  名称：

  Efficient Synthesis ofO-,S-,N- andC-Glycosides of 2-Amino-2-Deoxy-d-Glucopyranose from Glycosyl Iodides

  摘要：

  在温和条件下，受保护的D-葡糖胺的糖基碘化物就地生成，并与各种亲核试剂偶联，以良好产率提供相应的β-糖苷。

  DOI：

  10.1055/s-2003-44978

文献信息

• A comparative study of the influence of some protecting groups on the reactivity of d-glucosamine acceptors with a galactofuranosyl donor
  作者：María L. Bohn、María I. Colombo、Carlos A. Stortz、Edmundo A. Rúveda

  DOI：10.1016/j.carres.2006.03.030

  日期：2006.7

  experiments with a galactofuranosyl trichloroacetimidate donor were performed with glucosamine acceptors having a free 4-OH group and carrying different protecting groups at N-2, O-3, and O-6. The most reactive acceptor is the N-dimethylmaleimido 3,6-di-O-benzylated derivative (6c), which reacts even faster than the oxazolidinone 1a. Molecular orbital calculations have helped to rationalize these experimental

  使用具有游离4-OH基团且在N-2，O-3和O-6处带有不同保护基的葡糖胺受体，进行了半乳糖呋喃糖基三氯乙酰亚氨酸酯供体的竞争性糖基化实验。反应性最高的受体是N-二甲基马来酰亚胺基3,6-二-O-苄基化衍生物（6c），其反应甚至比恶唑烷酮1a还要快。分子轨道计算已根据供体和受体之间发生的硬-硬反应，帮助合理化了这些实验事实。
• 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.