3-azido-2,4-di-O-benzyl-3-deoxy-α-D-glucopyranosyl-(1→1')-3'-azido-2',4'-di-O-benzyl-3'-deoxy-a-D-glucopyranoside | 1417719-95-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-azido-2,4-di-O-benzyl-3-deoxy-α-D-glucopyranosyl-(1→1')-3'-azido-2',4'-di-O-benzyl-3'-deoxy-a-D-glucopyranoside
• CAS: 1417719-95-9
• 化学式: C₄₀H₄₄N₆O₉
• 分子量: 752.824
• InChiKey: NQSMVQPPPRUTPG-QKYQEKRYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.14
• 重原子数：
  55.0
• 可旋转键数：
  18.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  202.59
• 氢给体数：
  2.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  3-azido-2,4-di-O-benzyl-3-deoxy-α-D-glucopyranosyl-(1→1')-3'-azido-2',4'-di-O-benzyl-3'-deoxy-a-D-glucopyranoside 在 palladium(II) hydroxide 、 肼 、 溶剂黄146 作用下， 以 甲醇 、 水 为溶剂， 反应 40.0h， 以98%的产率得到3-amino-3-deoxyα-D-glucopyranosyl-(1→1')-3'-amino-3'-deoxy-α-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of 3,3′-neotrehalosadiamine and related 1,1′-aminodisaccharides using disarmed, armed, and superarmed building blocks

  摘要：

  Here we report a high yielding, stereoselective synthesis of the naturally occurring 1,1'-disaccharide neotrehalosadiamine (NTD) and some related analogs. Following an eleven-step sequence, seven of which did not require chromatographic separation, NTD was generated in 60% overall yield from the inexpensive, commercially available precursor 1,2:5,6-di-O-isopropylidene-alpha-D-glucofuranose. The key alpha,beta-linkage of NTD was formed in a highly stereoselective manner by taking advantage of the participating effect of the acyl group at O-2 of the donor glycoside. The influence of electronic effects of disarmed, armed, and superarmed glycosyl donors and acceptors on the outcome of 1,1'-glycosidation was also observed. Antibacterial studies using NTD and its analogs show detectable but weak antistaphylococcal activity. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.10.058
• 作为产物：
  描述：

  6-O-acetyl-3-azido-2,4-di-O-benzyl-3-deoxy-a-D-glucopyranosyl-(1→1')-6-O-acetyl-3'-azido-2',4'-di-O-benzyl-3'-deoxy-a-D-glucopyranoside 在 sodium 作用下， 以 甲醇 为溶剂， 反应 0.08h， 以0.286 g的产率得到3-azido-2,4-di-O-benzyl-3-deoxy-α-D-glucopyranosyl-(1→1')-3'-azido-2',4'-di-O-benzyl-3'-deoxy-a-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of 3,3′-neotrehalosadiamine and related 1,1′-aminodisaccharides using disarmed, armed, and superarmed building blocks

  摘要：

  Here we report a high yielding, stereoselective synthesis of the naturally occurring 1,1'-disaccharide neotrehalosadiamine (NTD) and some related analogs. Following an eleven-step sequence, seven of which did not require chromatographic separation, NTD was generated in 60% overall yield from the inexpensive, commercially available precursor 1,2:5,6-di-O-isopropylidene-alpha-D-glucofuranose. The key alpha,beta-linkage of NTD was formed in a highly stereoselective manner by taking advantage of the participating effect of the acyl group at O-2 of the donor glycoside. The influence of electronic effects of disarmed, armed, and superarmed glycosyl donors and acceptors on the outcome of 1,1'-glycosidation was also observed. Antibacterial studies using NTD and its analogs show detectable but weak antistaphylococcal activity. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.10.058