(2S,3S,4R,5R,6R)-4,5-Bis-benzyloxy-6-hydroxymethyl-2-((2R,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-3-ol | 197649-30-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3S,4R,5R,6R)-4,5-Bis-benzyloxy-6-hydroxymethyl-2-((2R,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-3-ol
• CAS: 197649-30-2
• 化学式: C₄₈H₅₄O₁₁
• 分子量: 806.95
• InChiKey: UWSOPYSRLWZBHT-SQNGJABZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.38
• 重原子数：
  59.0
• 可旋转键数：
  20.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  123.53
• 氢给体数：
  2.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  2,3,6,2',3',4',6'-hepta-O-acetyl-α-D-lactosyl trichloroacetimidate 、 (2S,3S,4R,5R,6R)-4,5-Bis-benzyloxy-6-hydroxymethyl-2-((2R,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-3-ol 在 molecular sieve 、 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 以57%的产率得到methyl (2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->4)-(2,3,6-tri-O-acetyl-β-D-glucopyranosyl)-(1->6)-(3,4-di-O-benzyl-α-D-mannopyranosyl)-(1->6)-(2,3,4-tri-O-benzyl-β-D-mannopyranoside)
  参考文献：
  名称：

  Studies on the synthesis of two tetrasaccharides and the reactivity difference between them

  摘要：

  Studies on the reactivity of two synthetic tetrasaccharides as glycosyl accepters showed that condensation of the methyl alpha-glycoside with a disaccharide donor afforded a hexasaccharide, but condensation of the methyl beta-glycoside with the disaccharide did not yield the corresponding hexasaccharide under the same conditions. A combination of theoretical results and 2D NMR indicated that the reactivity difference between the methyl alpha-glycoside and the methyl beta-glycoside was determined mainly by steric effects. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0008-6215(97)00169-9
• 作为产物：
  描述：

  Acetic acid (2S,3S,4S,5R,6R)-6-acetoxymethyl-4,5-bis-benzyloxy-2-((2R,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-3-yl ester 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 30.0h， 以95%的产率得到(2S,3S,4R,5R,6R)-4,5-Bis-benzyloxy-6-hydroxymethyl-2-((2R,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-3-ol
  参考文献：
  名称：

  Studies on the synthesis of two tetrasaccharides and the reactivity difference between them

  摘要：

  Studies on the reactivity of two synthetic tetrasaccharides as glycosyl accepters showed that condensation of the methyl alpha-glycoside with a disaccharide donor afforded a hexasaccharide, but condensation of the methyl beta-glycoside with the disaccharide did not yield the corresponding hexasaccharide under the same conditions. A combination of theoretical results and 2D NMR indicated that the reactivity difference between the methyl alpha-glycoside and the methyl beta-glycoside was determined mainly by steric effects. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0008-6215(97)00169-9