O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-(1->4)-O-(2,3,6-tri-O-acetyl-β-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranosyl 3,4,6-tri-O-acetyl-2-deoxy-α-D-arabino-hexopyranoside | 212266-54-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-(1->4)-O-(2,3,6-tri-O-acetyl-β-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranosyl 3,4,6-tri-O-acetyl-2-deoxy-α-D-arabino-hexopyranoside
• CAS: 212266-54-1
• 化学式: C₆₅H₈₀O₃₀
• 分子量: 1341.33
• InChiKey: QWTHRZBYITYEDF-DXTLXEQCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.66
• 重原子数：
  95.0
• 可旋转键数：
  29.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  355.3
• 氢给体数：
  0.0
• 氢受体数：
  30.0

反应信息

• 作为反应物：
  描述：

  O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-(1->4)-O-(2,3,6-tri-O-acetyl-β-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranosyl 3,4,6-tri-O-acetyl-2-deoxy-α-D-arabino-hexopyranoside 在 palladium on activated charcoal 氢气 、 sodium methylate 作用下， 以 甲醇 、 乙二醇二甲醚 、 乙醇 、 水 为溶剂， 25.0 ℃ 、110.0 kPa 条件下， 反应 20.0h， 生成 Glc(a1-4)Glc(b1-4)Glc(a1-1a)2-deoxy-D-araHex
  参考文献：
  名称：

  The Synthesis of the 2- and 2'-Monodeoxygenated Analogues of β-Maltosyl-(1→4)-Trehalose

  摘要：

  Two derivatives of beta-maltosyl-(1-->4)-trehalose monodeoxygenated at C-2 or C-2' have been synthesized in [2+2] block syntheses. N-Iodosuccinimide-mediated coupling of tetra-O-benzyl-glucose to tri-O-acetyl-D-glucal followed by O-acetylation furnished 3,4,6-tri-O-acetyl-2-deoxy-2-iodo-alpha-D-mannopyranosyl 2,3,4,6-tetra-O-benzyl-alpha-D-glucopyranoside (7), which was used as a starting material for both tetrasaccharides. For the preparation of the 2'-monodeoxygenated saccharide the deoxyiodo pyranose moiety of 7 was further elaborated by de-O-acetylation, O-benzylidenation, O-benzylation, and selective reductive opening of the benzylidene acetal to give glycosyl acceptor 10. Glycosylation with hepta-O-acetylmaltosyl bromide and deprotection including removal of the iodo substituent afforded the 2'-deoxymaltosyl-(1-->4)-trehalose 14. On the other hand, the non-iodinated pyranose moiety of 7 was transformed to a glycosyl acceptor. The removal of the benzyl groups of 7 necessitated also the reduction of the iodo group at this early stage. The resulting 3,4,6-tri-O-acetyl-2-deoxy-alpha-D-arabino-hexopyranosyl alpha-D-glucopyranoside was subjected to a similar reaction sequence as above to finally result in the 2-deoxymaltosyl-(1-->4)-trehalose 22.

  DOI：

  10.1080/07328309808002338
• 作为产物：
  描述：

  2-deoxy-2-iodo-α-D-mannopyranosyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside 在 palladium on activated charcoal 盐酸 、 三氟甲磺酸 、 3 Angstroem MS 、 氢气 、 silver trifluoromethanesulfonate 、 sodium cyanoborohydride 、 1,1,3,3-四甲基脲 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 吡啶 、 乙醚 、 乙醇 、 二氯甲烷 、 环己烷 为溶剂， 25.0 ℃ 、110.0 kPa 条件下， 反应 44.0h， 生成 O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-(1->4)-O-(2,3,6-tri-O-acetyl-β-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranosyl 3,4,6-tri-O-acetyl-2-deoxy-α-D-arabino-hexopyranoside
  参考文献：
  名称：

  The Synthesis of the 2- and 2'-Monodeoxygenated Analogues of β-Maltosyl-(1→4)-Trehalose

  摘要：

  Two derivatives of beta-maltosyl-(1-->4)-trehalose monodeoxygenated at C-2 or C-2' have been synthesized in [2+2] block syntheses. N-Iodosuccinimide-mediated coupling of tetra-O-benzyl-glucose to tri-O-acetyl-D-glucal followed by O-acetylation furnished 3,4,6-tri-O-acetyl-2-deoxy-2-iodo-alpha-D-mannopyranosyl 2,3,4,6-tetra-O-benzyl-alpha-D-glucopyranoside (7), which was used as a starting material for both tetrasaccharides. For the preparation of the 2'-monodeoxygenated saccharide the deoxyiodo pyranose moiety of 7 was further elaborated by de-O-acetylation, O-benzylidenation, O-benzylation, and selective reductive opening of the benzylidene acetal to give glycosyl acceptor 10. Glycosylation with hepta-O-acetylmaltosyl bromide and deprotection including removal of the iodo substituent afforded the 2'-deoxymaltosyl-(1-->4)-trehalose 14. On the other hand, the non-iodinated pyranose moiety of 7 was transformed to a glycosyl acceptor. The removal of the benzyl groups of 7 necessitated also the reduction of the iodo group at this early stage. The resulting 3,4,6-tri-O-acetyl-2-deoxy-alpha-D-arabino-hexopyranosyl alpha-D-glucopyranoside was subjected to a similar reaction sequence as above to finally result in the 2-deoxymaltosyl-(1-->4)-trehalose 22.

  DOI：

  10.1080/07328309808002338