methyl 6-O-benzoyl-2-deoxy-2-dimethylmaleimido-β-D-glucopyranoside | 1000403-58-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 6-O-benzoyl-2-deoxy-2-dimethylmaleimido-β-D-glucopyranoside
• 英文别名: [(2R,3S,4R,5R,6R)-5-(3,4-dimethyl-2,5-dioxopyrrol-1-yl)-3,4-dihydroxy-6-methoxyoxan-2-yl]methyl benzoate
• CAS: 1000403-58-6
• 化学式: C₂₀H₂₃NO₈
• 分子量: 405.405
• InChiKey: FWUUJVRLCFIGNF-QHXDDQSASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  123
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  methyl 6-O-benzoyl-2-deoxy-2-dimethylmaleimido-β-D-glucopyranoside 、 2,3,5,6-tetra-O-benzoyl-β-D-galactofuranosyl trichloroacetimidate 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 0.5h， 以37%的产率得到[(2R,3S,4R,5R,6R)-4-[(2R,3R,4S,5S)-3,4-dibenzoyloxy-5-[(1R)-1,2-dibenzoyloxyethyl]oxolan-2-yl]oxy-5-(3,4-dimethyl-2,5-dioxopyrrol-1-yl)-3-hydroxy-6-methoxyoxan-2-yl]methyl benzoate
  参考文献：
  名称：

  Differential O-3/O-4 regioselectivity in the glycosylation of α and β anomers of 6-O-substituted N-dimethylmaleoyl-protected d-glucosamine acceptors

  摘要：

  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.

  DOI：

  10.1016/j.carres.2007.08.006
• 作为产物：
  描述：

  methyl 6-O-benzyl-2-deoxy-2-dimethylmaleimido-α-D-glucopyranoside 、 苯甲酰氯 在 吡啶 作用下， 以55%的产率得到methyl 6-O-benzoyl-2-deoxy-2-dimethylmaleimido-β-D-glucopyranoside
  参考文献：
  名称：

  Differential O-3/O-4 regioselectivity in the glycosylation of α and β anomers of 6-O-substituted N-dimethylmaleoyl-protected d-glucosamine acceptors

  摘要：

  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.

  DOI：

  10.1016/j.carres.2007.08.006

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.