benzyl 2-acetamido-2-deoxy-4,6-O-(di-tert-butylsilandiyl)-3-O-methyl-α-D-glucopyranose | 1092110-63-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl 2-acetamido-2-deoxy-4,6-O-(di-tert-butylsilandiyl)-3-O-methyl-α-D-glucopyranose
• 英文别名: N-[(4aR,6S,7R,8R,8aS)-2,2-ditert-butyl-8-methoxy-6-phenylmethoxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3,2]dioxasilin-7-yl]acetamide
• CAS: 1092110-63-8
• 化学式: C₂₄H₃₉NO₆Si
• 分子量: 465.662
• InChiKey: MTLAMBIILUYDRF-LMYCIYFBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.91
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  75.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  benzyl 2-acetamido-2-deoxy-4,6-O-(di-tert-butylsilandiyl)-3-O-methyl-α-D-glucopyranose 在 Pd(OH)2/C 、 氢气 、 溶剂黄146 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 16.0h， 以97%的产率得到2-acetamido-2-deoxy-4,6-O-(di-tert-butylsilandiyl)-3-O-methyl-D-glucopyranose
  参考文献：
  名称：

  Synthesis of Sugar Nucleotides by Application of Phosphoramidites

  摘要：

  A new method for the construction of pyrophosphates is reported based on the coupling of a sugar phosphate and a nucleoside phosphoramidite. The in situ formed phosphate-phosphite intermediate Was subsequently oxidized with tBuOOH. Three UDP-N-acetylglucosamine derivatives were prepared using this one-pot procedure in good yields.

  DOI：

  10.1021/jo802021t
• 作为产物：
  描述：

  benzyl 2-acetamido-2-deoxy-4,6-O-(di-tert-butylsilanediyl)-α-D-glucopyranose 、 三甲基硅烷化重氮甲烷 在 三氟化硼乙醚 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 0.75h， 以62%的产率得到benzyl 2-acetamido-2-deoxy-4,6-O-(di-tert-butylsilandiyl)-3-O-methyl-α-D-glucopyranose
  参考文献：
  名称：

  Synthesis of Sugar Nucleotides by Application of Phosphoramidites

  摘要：

  A new method for the construction of pyrophosphates is reported based on the coupling of a sugar phosphate and a nucleoside phosphoramidite. The in situ formed phosphate-phosphite intermediate Was subsequently oxidized with tBuOOH. Three UDP-N-acetylglucosamine derivatives were prepared using this one-pot procedure in good yields.

  DOI：

  10.1021/jo802021t

文献信息

• Synthesis of Sugar Nucleotides by Application of Phosphoramidites
  作者：Henrik Gold、Pieter van Delft、Nico Meeuwenoord、Jeroen D. C. Codée、Dmitri V. Filippov、Gerrit Eggink、Herman S. Overkleeft、Gijs A. van der Marel

  DOI：10.1021/jo802021t

  日期：2008.12.5

  A new method for the construction of pyrophosphates is reported based on the coupling of a sugar phosphate and a nucleoside phosphoramidite. The in situ formed phosphate-phosphite intermediate Was subsequently oxidized with tBuOOH. Three UDP-N-acetylglucosamine derivatives were prepared using this one-pot procedure in good yields.