3,4,6-tri-O-acetyl-2-deoxy-2-iodo-α-D-mannopyranosyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside | 212266-43-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,4,6-tri-O-acetyl-2-deoxy-2-iodo-α-D-mannopyranosyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside
• CAS: 212266-43-8
• 化学式: C₄₆H₅₁IO₁₃
• 分子量: 938.808
• InChiKey: WFBBTQLCAIRGLB-SCHRWIETSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.66
• 重原子数：
  60.0
• 可旋转键数：
  19.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  143.51
• 氢给体数：
  0.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  3,4,6-tri-O-acetyl-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 、 sodium cyanoborohydride 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醚 、 乙醇 、 二氯甲烷 、 环己烷 为溶剂， 25.0 ℃ 、110.0 kPa 条件下， 反应 19.0h， 生成 Acetic acid (2R,3S,4R,6R)-3-acetoxy-2-acetoxymethyl-6-((2R,3R,4S,5R,6R)-3,4-bis-benzyloxy-6-benzyloxymethyl-5-hydroxy-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yl ester
  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：

  Acetic acid (2R,3R,4S)-3-acetoxy-2-acetoxymethyl-5-iodo-6-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yl ester 在 sodium carbonate 作用下， 以 吡啶 、 甲醇 、 水 为溶剂， 反应 23.0h， 生成 3,4,6-tri-O-acetyl-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