benzyl 3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido-β-D-glucopyranoside | 340290-40-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl 3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido-β-D-glucopyranoside
• 英文别名: 1-[(2R,3R,4R,5S,6R)-5-hydroxy-2,4-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-yl]-3,4-dimethylpyrrole-2,5-dione
• CAS: 340290-40-6
• 化学式: C₃₃H₃₅NO₇
• 分子量: 557.643
• InChiKey: RLBSQJANWAVNPW-XSETXXIFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  41
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  benzyl 3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido-β-D-glucopyranoside 、 3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido-4-phenoxyacetyl-D-glucopyranoside trichloroacetimidiate 在 三氟甲磺酸三甲基硅酯 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以65%的产率得到benzyl 3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido-4-O-phenoxyacetyl-β-D-glucopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of chitotetraose and chitohexaose based on dimethylmaleoyl protection

  摘要：

  tert-Butyldimethylsilyl 3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido-beta -D-glucopyranoside was readily transformed into the disaccharide glycosyl donor, 3,4,6-tri-O-acetyl-2-deoxy-2-dimethylmaleimido-beta -D-glucopyranosyl-(1 --> 4)-3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido-alpha/beta -D-glucopyranosyl trichloroacetimidate, and the disaccharide glycosyl acceptor, tert-butyldimethylsilyl 3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido-beta -D-glucopyranosyl-(1 --> 4)-3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido-beta -D-glucopyranoside. A TMSOTf-catalysed coupling of the acceptor with the donor afforded the respective tetrasaccharide derivative, which can be transformed to chitotetraose. tert-Butyldimethylsilyl 3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido-4-O-phenoxyacetyl-beta -D-glucopyranosyl-(1 --> 4)-3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido-beta -D-glucopyranoside was converted into donor 3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido-4-O-phenoxyacetyl-beta -D-glucopyranosyl- (1 --> 4)-3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido-beta -D-glucopyranosyl trichloroacetimidate. Its coupling with benzyl 3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido- beta -D-glucopyranosyl-(1 --> 4)-3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido-beta -D-glucopyranoside, followed by dephenoxyacetylation, gave benzyl 3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimiido-beta -D-glucopyranosyl- (1 --> 4)-3,6-di-O-benzyl-2-deoxy-2-dimethyimaleimido-beta -D-glucopyranosyl-(1 --> 4)- 3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido- beta -D-glucopyranosyl-(1 --> 4)-3.6-di-O-benzyl-2-deoxy-2-dimethylmaleimido-beta -D-glucopyranoside, whose glycosylation furnished, after replacement of the DMM-group by the acetyl moiety and subsequent deprotection, chitohexaose. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(01)00024-6
• 作为产物：
  描述：

  benzyl 3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido-4-O-phenoxyacetyl-β-D-glucopyranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以83%的产率得到benzyl 3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of chitotetraose and chitohexaose based on dimethylmaleoyl protection

  摘要：

  tert-Butyldimethylsilyl 3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido-beta -D-glucopyranoside was readily transformed into the disaccharide glycosyl donor, 3,4,6-tri-O-acetyl-2-deoxy-2-dimethylmaleimido-beta -D-glucopyranosyl-(1 --> 4)-3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido-alpha/beta -D-glucopyranosyl trichloroacetimidate, and the disaccharide glycosyl acceptor, tert-butyldimethylsilyl 3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido-beta -D-glucopyranosyl-(1 --> 4)-3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido-beta -D-glucopyranoside. A TMSOTf-catalysed coupling of the acceptor with the donor afforded the respective tetrasaccharide derivative, which can be transformed to chitotetraose. tert-Butyldimethylsilyl 3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido-4-O-phenoxyacetyl-beta -D-glucopyranosyl-(1 --> 4)-3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido-beta -D-glucopyranoside was converted into donor 3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido-4-O-phenoxyacetyl-beta -D-glucopyranosyl- (1 --> 4)-3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido-beta -D-glucopyranosyl trichloroacetimidate. Its coupling with benzyl 3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido- beta -D-glucopyranosyl-(1 --> 4)-3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido-beta -D-glucopyranoside, followed by dephenoxyacetylation, gave benzyl 3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimiido-beta -D-glucopyranosyl- (1 --> 4)-3,6-di-O-benzyl-2-deoxy-2-dimethyimaleimido-beta -D-glucopyranosyl-(1 --> 4)- 3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido- beta -D-glucopyranosyl-(1 --> 4)-3.6-di-O-benzyl-2-deoxy-2-dimethylmaleimido-beta -D-glucopyranoside, whose glycosylation furnished, after replacement of the DMM-group by the acetyl moiety and subsequent deprotection, chitohexaose. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(01)00024-6

文献信息

• Synthesis of chitotetraose and chitohexaose based on dimethylmaleoyl protection
  作者：Mohamed R.E Aly、El-Sayed I Ibrahim、El Sayed H El Ashry、Richard R Schmidt

  DOI：10.1016/s0008-6215(01)00024-6

  日期：2001.3

  tert-Butyldimethylsilyl 3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido-beta -D-glucopyranoside was readily transformed into the disaccharide glycosyl donor, 3,4,6-tri-O-acetyl-2-deoxy-2-dimethylmaleimido-beta -D-glucopyranosyl-(1 --> 4)-3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido-alpha/beta -D-glucopyranosyl trichloroacetimidate, and the disaccharide glycosyl acceptor, tert-butyldimethylsilyl 3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido-beta -D-glucopyranosyl-(1 --> 4)-3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido-beta -D-glucopyranoside. A TMSOTf-catalysed coupling of the acceptor with the donor afforded the respective tetrasaccharide derivative, which can be transformed to chitotetraose. tert-Butyldimethylsilyl 3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido-4-O-phenoxyacetyl-beta -D-glucopyranosyl-(1 --> 4)-3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido-beta -D-glucopyranoside was converted into donor 3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido-4-O-phenoxyacetyl-beta -D-glucopyranosyl- (1 --> 4)-3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido-beta -D-glucopyranosyl trichloroacetimidate. Its coupling with benzyl 3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido- beta -D-glucopyranosyl-(1 --> 4)-3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido-beta -D-glucopyranoside, followed by dephenoxyacetylation, gave benzyl 3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimiido-beta -D-glucopyranosyl- (1 --> 4)-3,6-di-O-benzyl-2-deoxy-2-dimethyimaleimido-beta -D-glucopyranosyl-(1 --> 4)- 3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido- beta -D-glucopyranosyl-(1 --> 4)-3.6-di-O-benzyl-2-deoxy-2-dimethylmaleimido-beta -D-glucopyranoside, whose glycosylation furnished, after replacement of the DMM-group by the acetyl moiety and subsequent deprotection, chitohexaose. (C) 2001 Elsevier Science Ltd. All rights reserved.