methyl 4-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-2,3,6-tri-O-benzoyl-α-D-galactopyranoside | 67109-87-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 4-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-2,3,6-tri-O-benzoyl-α-D-galactopyranoside
• 英文别名: Bn(-2)[Bn(-3)][Bn(-4)][Bn(-6)]Gal(a1-4)[Bz(-2)][Bz(-3)][Bz(-6)]a-Gal1Me；[(2R,3S,4S,5R,6S)-4,5-dibenzoyloxy-6-methoxy-3-[(2R,3R,4S,5S,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxyoxan-2-yl]methyl benzoate
• CAS: 67109-87-9
• 化学式: C₆₂H₆₀O₁₄
• 分子量: 1029.15
• InChiKey: UDWRZJBERYQDND-ZHVGZRQCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.1
• 重原子数：
  76
• 可旋转键数：
  26
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  153
• 氢给体数：
  0
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  methyl 4-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-2,3,6-tri-O-benzoyl-α-D-galactopyranoside 在 palladium over charcoal 氢气 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以95%的产率得到methyl 4-O-(α-D-galactopyranosyl)-2,3,6-tri-O-benzoyl-α-D-galactopyranoside
  参考文献：
  名称：

  WO2006/55437

  摘要：

  公开号：
• 作为产物：
  描述：

  pent-4-enyl O-α-D-galactopyranoside 在 N-碘代丁二酰亚胺 、 4 A molecular sieve 、 三乙基硅基三氟甲磺酸酯 、 sodium hydride 作用下， 反应 9.75h， 生成 methyl 4-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-2,3,6-tri-O-benzoyl-α-D-galactopyranoside
  参考文献：
  名称：

  Glycosidase-catalysed synthesis of glycosides by an improved procedure for reverse hydrolysis: application to the chemoenzymatic synthesis of galactopyranosyl-(1→4)-O-α-galactopyranoside derivatives

  摘要：

  beta-Galactosidase from Aspergillus oryzae, alpha-galactosidase from Aspergillus niger, beta-mannosidase from He[ir pomatia and beta-glucosidase from almond were used to synthesise different glycosides by reverse hydrolysis: Glc beta O(CH2)(6)OH 1 was obtained in 61% yield, beta-D-Glc-O(CH2)(3)CH=CH2 2 in 50% yield, beta-D-Glc-O(CH2)(2)Si(Me)(3) 3 in 11% yield, beta-D-Gal-O(CH2)(6)OH 4 in 48% yield, beta-D-Gal-O(CH2)(3)CH=CH2 5 in 22% yield, alpha-D-Gal-O(CH2)(6)OH 6 in 47% yield, alpha-D-Gal-O(CH2)(3)CH=CH2 7 in 37% yield and beta-D-ManO(CH2)(6)OH 8 in 12% yield. Using the appropriate glycosides methyl O-(2,3,4,6-tetra-O-benzyl-alpha-galactopyranosyl)-(1-->4)-2,3,6-tri-O-benzoyl-1-O-alpha-D-galactopyranoside 11 and 6'-benzoylhexyl-O-(2,3,4,6-tetra alpha-O-benzyl-(1-->4)-2,3,6-tri-O-benzoyl-1-O-beta-D-galactopyranoside 15 were synthesised. This chemoenzymatic approach avoided at least four chemical steps that would have been necessary in a conventional synthesis. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00238-8

文献信息

• WO2006/55437
  申请人：——

  公开号：——

  公开（公告）日：——
• Glycosidase-catalysed synthesis of glycosides by an improved procedure for reverse hydrolysis: application to the chemoenzymatic synthesis of galactopyranosyl-(1→4)-O-α-galactopyranoside derivatives
  作者：Gabin Vic、Jeremy J. Hastings、David H.G. Crout

  DOI：10.1016/0957-4166(96)00238-8

  日期：1996.7

  beta-Galactosidase from Aspergillus oryzae, alpha-galactosidase from Aspergillus niger, beta-mannosidase from He[ir pomatia and beta-glucosidase from almond were used to synthesise different glycosides by reverse hydrolysis: Glc beta O(CH2)(6)OH 1 was obtained in 61% yield, beta-D-Glc-O(CH2)(3)CH=CH2 2 in 50% yield, beta-D-Glc-O(CH2)(2)Si(Me)(3) 3 in 11% yield, beta-D-Gal-O(CH2)(6)OH 4 in 48% yield, beta-D-Gal-O(CH2)(3)CH=CH2 5 in 22% yield, alpha-D-Gal-O(CH2)(6)OH 6 in 47% yield, alpha-D-Gal-O(CH2)(3)CH=CH2 7 in 37% yield and beta-D-ManO(CH2)(6)OH 8 in 12% yield. Using the appropriate glycosides methyl O-(2,3,4,6-tetra-O-benzyl-alpha-galactopyranosyl)-(1-->4)-2,3,6-tri-O-benzoyl-1-O-alpha-D-galactopyranoside 11 and 6'-benzoylhexyl-O-(2,3,4,6-tetra alpha-O-benzyl-(1-->4)-2,3,6-tri-O-benzoyl-1-O-beta-D-galactopyranoside 15 were synthesised. This chemoenzymatic approach avoided at least four chemical steps that would have been necessary in a conventional synthesis. Copyright (C) 1996 Elsevier Science Ltd