methyl 2,3,4-tri-O-acetyl-α-D-glucopyranosyl-(1->4)-2,3-di-O-acetyl-α-D-glucopyranosyl-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside | 1092071-15-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3,4-tri-O-acetyl-α-D-glucopyranosyl-(1->4)-2,3-di-O-acetyl-α-D-glucopyranosyl-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside
• 英文别名: Glc2Ac3Ac4Ac(a1-4)Glc2Ac3Ac(a1-4)b-Glc1Me2Ac3Ac6Ac；[(2R,3R,4S,5R,6R)-4,5-diacetyloxy-3-[(2R,3R,4S,5R,6R)-3,4-diacetyloxy-6-(hydroxymethyl)-5-[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-6-methoxyoxan-2-yl]methyl acetate
• CAS: 1092071-15-2
• 化学式: C₃₅H₅₀O₂₄
• 分子量: 854.768
• InChiKey: JFSNYEWKYPIQGU-FRJGCGJYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.3
• 重原子数：
  59
• 可旋转键数：
  24
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  306
• 氢给体数：
  2
• 氢受体数：
  24

反应信息

• 作为反应物：
  描述：

  methyl 2,3,4-tri-O-acetyl-α-D-glucopyranosyl-(1->4)-2,3-di-O-acetyl-α-D-glucopyranosyl-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside 在 四氯化碳 、 三苯基膦 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 以77%的产率得到methyl 2,3,4-tri-O-acetyl-6-chloro-6-deoxy-α-D-glucopyranosyl-(1->4)-2,3-di-O-acetyl-6-chloro-6-deoxy-α-D-glucopyranosyl-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside
  参考文献：
  名称：

  Efficient regioselective chemical modifications of maltotriose: an easy access to oligosaccharidic scaffold

  摘要：

  Regioselective chlorination of fully unprotected maltotriose has given in high yield 1(I),2(I-III),3(I-III),4(III)-octa-O-acetyl-6(I-III)-trichloro-6(I-III)-trideoxymaltotriose. Moreover, regioselective ditritylation of methyl beta-maltotrioside has provided the two regioselectively C-6-disubstituted trisaccharides. Selective deprotection of these new compounds gives the corresponding diol and halogenated analogues, respectively, in good yield. All compounds have been completely characterized and the substitution pattern in the oligosaccharidic sequence has been elucidated. A new family of amphiphilic carbohydrates, namely the 6-deoxy-6-alkylthiomaltotriose derivatives, bearing either two or three thioalkyl hydrophobic chains, respectively, has been synthesized. Critical micellar concentration (CMC) values as well as the antimicrobial properties have been evaluated for amphiphilic compounds. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2008.04.035
• 作为产物：
  描述：

  methyl 2,3,4-tri-O-acetyl-6-O-trityl-α-D-glucopyranosyl-(1->4)-2,3-di-O-acetyl-6-O-trityl-α-D-glucopyranosyl-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside 在 Cl₆Fe 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以71%的产率得到methyl 2,3,4-tri-O-acetyl-α-D-glucopyranosyl-(1->4)-2,3-di-O-acetyl-α-D-glucopyranosyl-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside
  参考文献：
  名称：

  Efficient regioselective chemical modifications of maltotriose: an easy access to oligosaccharidic scaffold

  摘要：

  Regioselective chlorination of fully unprotected maltotriose has given in high yield 1(I),2(I-III),3(I-III),4(III)-octa-O-acetyl-6(I-III)-trichloro-6(I-III)-trideoxymaltotriose. Moreover, regioselective ditritylation of methyl beta-maltotrioside has provided the two regioselectively C-6-disubstituted trisaccharides. Selective deprotection of these new compounds gives the corresponding diol and halogenated analogues, respectively, in good yield. All compounds have been completely characterized and the substitution pattern in the oligosaccharidic sequence has been elucidated. A new family of amphiphilic carbohydrates, namely the 6-deoxy-6-alkylthiomaltotriose derivatives, bearing either two or three thioalkyl hydrophobic chains, respectively, has been synthesized. Critical micellar concentration (CMC) values as well as the antimicrobial properties have been evaluated for amphiphilic compounds. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2008.04.035