2-[(2S,3R,4R,5S,6R)-4-Benzyloxy-6-benzyloxymethyl-5-((3aS,4S,5aR,9aR,9bS)-2-ethoxy-2-methyl-8-phenyl-hexahydro-[1,3]dioxolo[4',5':4,5]pyrano[3,2-d][1,3]dioxin-4-yloxy)-2-ethylsulfanyl-tetrahydro-pyran-3-yl]-isoindole-1,3-dione | 142072-49-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-[(2S,3R,4R,5S,6R)-4-Benzyloxy-6-benzyloxymethyl-5-((3aS,4S,5aR,9aR,9bS)-2-ethoxy-2-methyl-8-phenyl-hexahydro-[1,3]dioxolo[4',5':4,5]pyrano[3,2-d][1,3]dioxin-4-yloxy)-2-ethylsulfanyl-tetrahydro-pyran-3-yl]-isoindole-1,3-dione
• CAS: 142072-49-9
• 化学式: C₄₇H₅₁NO₁₂S
• 分子量: 853.987
• InChiKey: GGTGKIHBNRELOM-NJIXYNRUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.65
• 重原子数：
  61.0
• 可旋转键数：
  15.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  129.68
• 氢给体数：
  0.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  2-[(2S,3R,4R,5S,6R)-4-Benzyloxy-6-benzyloxymethyl-5-((3aS,4S,5aR,9aR,9bS)-2-ethoxy-2-methyl-8-phenyl-hexahydro-[1,3]dioxolo[4',5':4,5]pyrano[3,2-d][1,3]dioxin-4-yloxy)-2-ethylsulfanyl-tetrahydro-pyran-3-yl]-isoindole-1,3-dione 在 4 A molecular sieve 、 silver trifluoromethanesulfonate 、 溶剂黄146 、 1,1,3,3-四甲基脲 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 甲苯 为溶剂， 反应 24.66h， 生成 ethyl O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-(1->3)-O-<(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-(1->6)>-O-(2-O-acetyl-β-D-mannopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of β-d-mannosides from β-d-glucosides via an intramolecular Sn2 reaction at C-2

  摘要：

  The selective synthesis of beta-D-mannosides was achieved by first synthesizing beta-D-glucosides that carry a N-phenylcarbamoyl protecting group at O-3. These derivatives were transformed into the corresponding beta-D-mannosides by intramolecular nucleophilic substitution with inversion of configuration at C-2, the O-triflyl group being the leaving group. Subsequent intramolecular attack of the neighboring carbamoyl group resulted in the formation of the 2,3-carbonate of the desired beta-D-mannoside.

  DOI：

  10.1016/s0008-6215(00)90561-5
• 作为产物：
  描述：

  乙基3,4,6-三-O-乙酰基-2-脱氧-2-邻苯二甲酰亚胺基-1-硫代-β-D-吡喃葡萄糖苷 在 吡啶 、 盐酸 、 甲醇 、 tetrafluoroboric acid 、 3 A molecular sieve 、 4 A molecular sieve 、 sodium methylate 、 silver trifluoromethanesulfonate 、 sodium hydride 、 sodium cyanoborohydride 、 potassium carbonate 、 对甲苯磺酸 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 、 苯 为溶剂， 反应 61.42h， 生成 2-[(2S,3R,4R,5S,6R)-4-Benzyloxy-6-benzyloxymethyl-5-((3aS,4S,5aR,9aR,9bS)-2-ethoxy-2-methyl-8-phenyl-hexahydro-[1,3]dioxolo[4',5':4,5]pyrano[3,2-d][1,3]dioxin-4-yloxy)-2-ethylsulfanyl-tetrahydro-pyran-3-yl]-isoindole-1,3-dione
  参考文献：
  名称：

  Synthesis of β-d-mannosides from β-d-glucosides via an intramolecular Sn2 reaction at C-2

  摘要：

  The selective synthesis of beta-D-mannosides was achieved by first synthesizing beta-D-glucosides that carry a N-phenylcarbamoyl protecting group at O-3. These derivatives were transformed into the corresponding beta-D-mannosides by intramolecular nucleophilic substitution with inversion of configuration at C-2, the O-triflyl group being the leaving group. Subsequent intramolecular attack of the neighboring carbamoyl group resulted in the formation of the 2,3-carbonate of the desired beta-D-mannoside.

  DOI：

  10.1016/s0008-6215(00)90561-5