2-aminoethyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside | 1185880-69-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-aminoethyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside
• 英文别名: [(2R,3R,4S,5R,6S)-3,4,5-triacetyloxy-6-(2-aminoethylsulfanyl)oxan-2-yl]methyl acetate
• CAS: 1185880-69-6
• 化学式: C₁₆H₂₅NO₉S
• 分子量: 407.442
• InChiKey: FWHUZVNWRGQXTG-LJIZCISZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  27
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  166
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  2-aminoethyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside 、 溴乙酸 、 2-甲氧基乙胺 、 alkaline earth salt of/the/ methylsulfuric acid 在 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 、
  参考文献：
  名称：

  On-Bead Peptoid Dimerization Induced by Incorporation of Glycosylated Bridging Units in Submonomer Solid-Phase Approach to Glycopeptoids

  摘要：

  A study on submonomer solid-phase synthesis of S-glycopeptoids has been carried out by screening different parameters. Dimeric species, featuring glycosylated bridging amino monomers, were found under suitable conditions. These dimers arise from an on-resin cross-linking reaction occurring with the incorporation of a glycoamino submonomer into the growing chain and subsequent nucleophilic attack of the resulting secondary amine to a still unreacted bromoacetylated unit. The arising byproduct can be regarded as a novel dimeric peptoid type.

  DOI：

  10.1021/acs.orglett.9b01242
• 作为产物：
  描述：

  2-溴乙胺氢溴酸盐 、 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl iodide 在 硫脲 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 1.33h， 生成 2-aminoethyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  An Efficient Modular Approach for the Assembly of S-Linked Glycopeptoids

  摘要：

  A short and convenient methodology for the synthesis of S-glycosylated peptoid models Is described. The thioglycosylated building blocks were prepared from proper peracetylated sugars via glycosyl iodides in a one-pot fashion and directly employed in a submonomer solidphase stategy.

  DOI：

  10.1021/ol901524k