dicyclohexylmethyl 6-O-(6-O-acetyl-2-O-benzoyl-3,4-di-O-benzyl-β-D-glucopyranosyl)-3-O-[(2-O-benzoyl-3,4,6-tri-O-benzyl-β-D-glucopyranosyl)]-2-O-benzoyl-1-thio-β-D-glucopyranoside | 250122-25-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: dicyclohexylmethyl 6-O-(6-O-acetyl-2-O-benzoyl-3,4-di-O-benzyl-β-D-glucopyranosyl)-3-O-[(2-O-benzoyl-3,4,6-tri-O-benzyl-β-D-glucopyranosyl)]-2-O-benzoyl-1-thio-β-D-glucopyranoside
• 英文别名: [(2S,3R,4S,5R,6R)-2-[(2R,3R,4S,5R,6S)-2-[[(2R,3R,4S,5R,6R)-6-(acetyloxymethyl)-3-benzoyloxy-4,5-bis(phenylmethoxy)oxan-2-yl]oxymethyl]-5-benzoyloxy-6-(dicyclohexylmethylsulfanyl)-3-hydroxyoxan-4-yl]oxy-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-yl] benzoate
• CAS: 250122-25-9
• 化学式: C₈₉H₉₈O₁₉S
• 分子量: 1503.81
• InChiKey: XQJNQHWJUAPNOO-VPCCIFLFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  16.1
• 重原子数：
  109
• 可旋转键数：
  37
• 环数：
  13.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  243
• 氢给体数：
  1
• 氢受体数：
  20

反应信息

• 作为反应物：
  描述：

  3-(苄氧羰基氨基)-1-丙醇 、 dicyclohexylmethyl 6-O-(6-O-acetyl-2-O-benzoyl-3,4-di-O-benzyl-β-D-glucopyranosyl)-3-O-[(2-O-benzoyl-3,4,6-tri-O-benzyl-β-D-glucopyranosyl)]-2-O-benzoyl-1-thio-β-D-glucopyranoside 在 N-碘代丁二酰亚胺 、 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 0.05h， 以74%的产率得到3-(benzyloxycarbonylamino)-1-propyl 6-O-(6-O-acetyl-2-O-benzoyl-3,4-di-O-benzyl-β-D-glucopyranosyl)-3-O-[(2-O-benzoyl-3,4,6-tri-O-benzyl-β-D-glucopyranosyl)]-2-O-benzoyl-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  Chemoselective Glycosylation Strategy for the Convergent Assembly of Phytoalexin-Elicitor Active Oligosaccharides and Their Photoreactive Derivatives

  摘要：

  A highly convergent route for the synthesis of branched glucosides having phytoalexin-elicitor activity has been developed. The readily available building blocks 2, 3, and 6 were used for the assembly of a core trisaccharide in two chemo- and regioselective glycosylations. Compound 7 was converted into the artificial spacer-containing glycosyl acceptor 9. Regioselective condensation of fragment 7 with 9 Zed to the formation of fully protected hexasaccharide 14. Deprotection of hexasaccharide 14 followed by the reaction with 4-azidosalicylate gave compound 1b. It was established that compound Ib is a photoreactive compound. Reaction time and conditions were established for photolysis of compound 1b and labeling with radioactive iodine. A soybean root binding site for an elicitor-active hepta-beta-glucoside bound compound 1b with the same affinity as the underivatized hepta-beta-glucoside.

  DOI：

  10.1021/jo990836o
• 作为产物：
  描述：

  ethyl 6-O-acetyl-2-O-benzoyl-3,4,6-tri-O-benzyl-1-thio-β-D-glucopyranoside 、 dicyclohexylmethyl 3-O-(2-O-benzoyl-3,4,6-tri-O-benzyl-β-D-glucopyranosyl)-2-O-benzoyl-1-thio-β-D-glucopyranoside 在 N-碘代丁二酰亚胺 、 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以50%的产率得到dicyclohexylmethyl 6-O-(6-O-acetyl-2-O-benzoyl-3,4-di-O-benzyl-β-D-glucopyranosyl)-3-O-[(2-O-benzoyl-3,4,6-tri-O-benzyl-β-D-glucopyranosyl)]-2-O-benzoyl-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  Chemoselective Glycosylation Strategy for the Convergent Assembly of Phytoalexin-Elicitor Active Oligosaccharides and Their Photoreactive Derivatives

  摘要：

  A highly convergent route for the synthesis of branched glucosides having phytoalexin-elicitor activity has been developed. The readily available building blocks 2, 3, and 6 were used for the assembly of a core trisaccharide in two chemo- and regioselective glycosylations. Compound 7 was converted into the artificial spacer-containing glycosyl acceptor 9. Regioselective condensation of fragment 7 with 9 Zed to the formation of fully protected hexasaccharide 14. Deprotection of hexasaccharide 14 followed by the reaction with 4-azidosalicylate gave compound 1b. It was established that compound Ib is a photoreactive compound. Reaction time and conditions were established for photolysis of compound 1b and labeling with radioactive iodine. A soybean root binding site for an elicitor-active hepta-beta-glucoside bound compound 1b with the same affinity as the underivatized hepta-beta-glucoside.

  DOI：

  10.1021/jo990836o