(2R,3S,4S,5R,6S)-3,4,5-tris(benzyloxy)-2-((benzyloxy)methyl)-6-(pent-4-en-1-yloxy)tetrahydro-2H-pyran | 125392-60-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2R,3S,4S,5R,6S)-3,4,5-tris(benzyloxy)-2-((benzyloxy)methyl)-6-(pent-4-en-1-yloxy)tetrahydro-2H-pyran
• 英文别名: (2S,3R,4S,5S,6R)-2-pent-4-enoxy-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxane
• CAS: 125392-60-1
• 化学式: C₃₉H₄₄O₆
• 分子量: 608.775
• InChiKey: UJKZBFGKKCLGDY-CHXCTFQWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  45
• 可旋转键数：
  18
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  甲基-D-半乳糖苷-2,3,6-三苯甲酸酯 、 (2R,3S,4S,5R,6S)-3,4,5-tris(benzyloxy)-2-((benzyloxy)methyl)-6-(pent-4-en-1-yloxy)tetrahydro-2H-pyran 在 N-碘代丁二酰亚胺 、 4 A molecular sieve 、 三乙基硅基三氟甲磺酸酯 作用下， 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
• 作为产物：
  描述：

  D-吡喃葡萄糖 在 sodium hydride 作用下， 以 水 为溶剂， 反应 28.5h， 生成 (2R,3S,4S,5R,6S)-3,4,5-tris(benzyloxy)-2-((benzyloxy)methyl)-6-(pent-4-en-1-yloxy)tetrahydro-2H-pyran
  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

• AuCl3-AgOTf promoted O-glycosylation using anomeric sulfoxides as glycosyl donors at room temperature
  作者：Ashokkumar Palanivel、Ande Chennaiah、Sateesh Dubbu、Asadulla Mallick、Yashwant D. Vankar

  DOI：10.1016/j.carres.2016.11.012

  日期：2017.1

  glycosyl donors using AuCl3/AgOTf reagent system has been described. Under optimal reaction conditions, both armed and disarmed glycosyl sulfoxide donors were found to react with a range of primary, secondary, and tertiary alcohol acceptors, and sugar derived glycosyl acceptors to afford the corresponding glycosides in moderate to good yields with predictable selectivity. The reactions are quick (20-60 min)

  已经描述了使用AuCl3 / AgOTf试剂系统将亚砜活化为糖基供体。在最佳反应条件下，发现武装和解除武装的糖基亚砜供体都与一定范围的伯，仲和叔醇受体和糖衍生的糖基受体反应，以中等到良好的产率提供了可预测的选择性的相应糖苷。反应快速（20-60分钟），在室温下容易进行，并且反应条件可耐受酸敏感性基团。
• 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