phenyl 3-azido-3-deoxy-6-O-p-methoxybenzyl-1-thio-β-D-glucopyranoside | 1417719-97-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 3-azido-3-deoxy-6-O-p-methoxybenzyl-1-thio-β-D-glucopyranoside
• CAS: 1417719-97-1
• 化学式: C₂₀H₂₃N₃O₅S
• 分子量: 417.486
• InChiKey: COTWZYOHWLGYSA-IVDHNXQLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.13
• 重原子数：
  29.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  116.91
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  phenyl 3-azido-3-deoxy-6-O-p-methoxybenzyl-1-thio-β-D-glucopyranoside 在 4-二甲氨基吡啶 、 N-溴代丁二酰亚胺(NBS) 、 caesium carbonate 作用下， 以 吡啶 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 11.75h， 生成 3-azido-2,4-di-O-tert-butyldimethylsilyl-3-deoxy-6-O-pmethoxybenzyl-α-D-glucopyranosyl trichloroacetimidate
  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：

  3-azido-1,3-dideoxy-1-(phenylsulfenyl)-2,4,6-tri-O-acetyl-β-D-gluco-pyranose 在 盐酸 、 sodium methylate 、 sodium cyanoborohydride 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 32.0h， 生成 phenyl 3-azido-3-deoxy-6-O-p-methoxybenzyl-1-thio-β-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