Phenyl-carbamic acid (2S,3R,4S,5R,6R)-2-[(2R,3S,4R,5R,6S)-4-benzyloxy-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-ethylsulfanyl-tetrahydro-pyran-3-yloxy]-3,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-4-yl ester | 115533-40-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Phenyl-carbamic acid (2S,3R,4S,5R,6R)-2-[(2R,3S,4R,5R,6S)-4-benzyloxy-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-ethylsulfanyl-tetrahydro-pyran-3-yloxy]-3,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-4-yl ester
• CAS: 115533-40-9
• 化学式: C₄₃H₄₆N₂O₁₂S
• 分子量: 814.91
• InChiKey: QKOQYESZARDKLR-CACULFRWSA-N

物化性质

• 沸点：
  927.8±65.0 °C(predicted)
• 密度：
  1.43±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.37
• 重原子数：
  58.0
• 可旋转键数：
  15.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  182.55
• 氢给体数：
  4.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  Phenyl-carbamic acid (2S,3R,4S,5R,6R)-2-[(2R,3S,4R,5R,6S)-4-benzyloxy-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-ethylsulfanyl-tetrahydro-pyran-3-yloxy]-3,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-4-yl ester 在 吡啶 、 甲醇 、 tetrafluoroboric acid 、 sodium methylate 、 N,N-二甲基甲酰胺 作用下， 以 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 2.67h， 生成 ethyl O-(4,6-O-benzylidene-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 盐酸 、 tetrafluoroboric acid 、 3 A molecular sieve 、 4 A molecular sieve 、 sodium methylate 、 silver trifluoromethanesulfonate 、 sodium hydride 、 sodium cyanoborohydride 、 potassium carbonate 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 为溶剂， 反应 57.75h， 生成 Phenyl-carbamic acid (2S,3R,4S,5R,6R)-2-[(2R,3S,4R,5R,6S)-4-benzyloxy-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-ethylsulfanyl-tetrahydro-pyran-3-yloxy]-3,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-4-yl ester
  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

文献信息

• Kunz, Horst; Guenther, Wolfgang, Angewandte Chemie, 1988, vol. 100, # 8, p. 1118 - 1119
  作者：Kunz, Horst、Guenther, Wolfgang

  DOI：——

  日期：——