methyl 6-O-benzyl-2-deoxy-2-dimethylmaleimido-α-D-glucopyranoside | 1000403-56-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 6-O-benzyl-2-deoxy-2-dimethylmaleimido-α-D-glucopyranoside
• 英文别名: 1-[(2S,3R,4R,5S,6R)-4,5-dihydroxy-2-methoxy-6-(phenylmethoxymethyl)oxan-3-yl]-3,4-dimethylpyrrole-2,5-dione
• CAS: 1000403-56-4
• 化学式: C₂₀H₂₅NO₇
• 分子量: 391.421
• InChiKey: LVHPIONMQRUHJX-RXFYRGCNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  106
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl 6-O-benzyl-2-deoxy-2-dimethylmaleimido-α-D-glucopyranoside 在 吡啶 、 4-二甲氨基吡啶 、 四丁基氟化铵 、 溶剂黄146 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 18.42h， 生成 methyl 2,3,4-tri-O-acetyl-6-O-benzyl-β-D-glucopyranosyl-(1→4)-3-O-acetyl-6-O-benzyl-2-deoxy-2-dimethylmaleimido-α-D-glucopyranoside
  参考文献：
  名称：

  Differential O-3/O-4 selectivity in the glycosylation of N-dimethylmaleoyl-protected hexosamine acceptors: effect of a conformationally armed (superarmed) glycosyl donor

  摘要：

  An assessment of the relative O-3/O-4 reactivities of both alpha- and beta-methyl glycosides of N-dimethylmaleoyl (DMM) glucosamine and allosamine acceptors protected at O-6 with a benzyl group using a D-glucopyranosyl conformationally armed donor (superarmed donor) counterpart is presented. The glycosylation of glucosamine derivatives followed the trends already observed for disarmed donors. On the other hand, the glycosylation of allosamine derivatives gave exclusively substitution on the equatorial O-4, in spite that with a disarmed donor the point of substitution is exclusively on the more hindered, electronically-preferred O-3. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2013.08.002
• 作为产物：
  描述：

  1-[(4aR,6S,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 在 硼烷-三甲胺络合物 、 三氟化硼乙醚 作用下， 以 乙腈 为溶剂， 以72%的产率得到methyl 6-O-benzyl-2-deoxy-2-dimethylmaleimido-α-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.
• Differential O-3/O-4 selectivity in the glycosylation of N-dimethylmaleoyl-protected hexosamine acceptors: effect of a conformationally armed (superarmed) glycosyl donor
  作者：F. Della Felice、Edmundo A. Rúveda、Carlos A. Stortz、María I. Colombo

  DOI：10.1016/j.carres.2013.08.002

  日期：2013.10

  An assessment of the relative O-3/O-4 reactivities of both alpha- and beta-methyl glycosides of N-dimethylmaleoyl (DMM) glucosamine and allosamine acceptors protected at O-6 with a benzyl group using a D-glucopyranosyl conformationally armed donor (superarmed donor) counterpart is presented. The glycosylation of glucosamine derivatives followed the trends already observed for disarmed donors. On the other hand, the glycosylation of allosamine derivatives gave exclusively substitution on the equatorial O-4, in spite that with a disarmed donor the point of substitution is exclusively on the more hindered, electronically-preferred O-3. (C) 2013 Elsevier Ltd. All rights reserved.