| 1000403-54-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• CAS: 1000403-54-2
• 化学式: C₁₃H₁₉NO₇
• 分子量: 301.296
• InChiKey: MORBCPNNXFBNPT-ACDNLYMZSA-N

物化性质

• 熔点：
  196.6-198.0 °C
• 沸点：
  516.5±50.0 °C(Predicted)
• 密度：
  1.45±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

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：

  、 苯甲酰氯 在 吡啶 作用下， 以74%的产率得到methyl 6-O-benzoyl-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
• 作为产物：
  描述：

  在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以92%的产率得到
  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