3,6-di-O-benzyl-2-deoxy-2-iodo-α-D-mannopyranosyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside | 212266-46-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,6-di-O-benzyl-2-deoxy-2-iodo-α-D-mannopyranosyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside
• CAS: 212266-46-1
• 化学式: C₅₄H₅₇IO₁₀
• 分子量: 992.945
• InChiKey: XVFBQSPDIHZUDQ-JZLSZLSTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.39
• 重原子数：
  65.0
• 可旋转键数：
  22.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  103.3
• 氢给体数：
  1.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  2,3,6,2',3',4',6'-hepta-O-acetyl-α-D-maltosyl bromide 、 3,6-di-O-benzyl-2-deoxy-2-iodo-α-D-mannopyranosyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside 在 silver trifluoromethanesulfonate 、 1,1,3,3-四甲基脲 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以54%的产率得到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)-3,6-di-O-benzyl-2-deoxy-2-iodo-α-D-mannopyranosyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside
  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 盐酸 、 三氟甲磺酸 、 3 Angstroem MS 、 sodium cyanoborohydride 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 环己烷 为溶剂， 反应 6.0h， 生成 3,6-di-O-benzyl-2-deoxy-2-iodo-α-D-mannopyranosyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside
  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