2-(4-nitrophenyl)ethyl 2-azido-4,6-O-benzylidene-2-deoxy-3-O-(4-methoxybenzyl)-β-D-mannopyranoside | 203056-90-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: 2-(4-nitrophenyl)ethyl 2-azido-4,6-O-benzylidene-2-deoxy-3-O-(4-methoxybenzyl)-β-D-mannopyranoside
• 英文别名: (2R,4aR,6R,7S,8R,8aS)-7-azido-8-[(4-methoxyphenyl)methoxy]-6-[2-(4-nitrophenyl)ethoxy]-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine
• CAS: 203056-90-0
• 化学式: C₂₉H₃₀N₄O₈
• 分子量: 562.579
• InChiKey: MIUIZSDKUBXKES-SMVCFURMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  41
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  116
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  2-(4-nitrophenyl)ethyl 2-azido-4,6-O-benzylidene-2-deoxy-3-O-(4-methoxybenzyl)-β-D-mannopyranoside 在 4 A molecular sieve 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 为溶剂， 反应 16.5h， 生成 α-N-succinimido-α-[2-(4-nitrophenyl)ethyl 2-azido-4,6-O-benzylidene-2-deoxy-3-O-(1,4,6-tri-O-benzyl-β-D-fructofuranosyl-3-O-yl)-β-D-mannopyranoside]-4-methoxytoluene
  参考文献：
  名称：

  Stereospecific Synthesis of β-d-Fructofuranosides Using Thioglycoside Donors and Internal Aglycon Delivery

  摘要：

  Stereospecific synthesis of beta-D-fructofuranosides has been accomplished by the application of an internal acceptor delivery approach. The acceptor, ethanol or monosaccharides, is initially tethered to the fructofuranose 3-hydroxyl group, adjacent to the anomeric center and on the beta-side of the furanose ring, as part of a mixed p-methoxybenzaldehyde acetal, which is formed by DDQ-oxidation of ethyl 1,4,6-tri-O-benzyl-3-O-(4-methoxybenzyl)-2-thio-D-fructofuranoside in the presence of the acceptor or of the p-methoxybenzylated acceptor in the presence of the corresponding 3-OH fructofuranoside. Then, activation of the thioglycoside with a thiophilic promoter allows the delivery of the acceptor from the acetal to the activated anomeric center to yield the beta-linked fructofuranoside in high yields (76-85%). If promoters with nonnucleophilic anions (triflate, perchlorate) are used, the intermediate acetal decomposes to produce the beta-fructofuranoside products as 3-OH derivatives. However, if NIS is used as promoter, the N-succinimide anion interacts with the benzylidene carbon to give the beta-fructofuranoside products as mixed fructofuranoside-3-O-yl N-succinimide p-methoxybenzaldehyde acetals.

  DOI：

  10.1021/jo970983r
• 作为产物：
  描述：

  4-甲氧基溴苄 、 2-(4-nitrophenyl)ethyl 2-azido-4,6-O-benzylidene-2-deoxy-β-D-mannopyranoside 在 barium hydroxide octahydrate 、 4 A molecular sieve 、 barium(II) oxide 作用下， 生成 2-(4-nitrophenyl)ethyl 2-azido-4,6-O-benzylidene-2-deoxy-3-O-(4-methoxybenzyl)-β-D-mannopyranoside
  参考文献：
  名称：

  Stereospecific Synthesis of β-d-Fructofuranosides Using Thioglycoside Donors and Internal Aglycon Delivery

  摘要：

  Stereospecific synthesis of beta-D-fructofuranosides has been accomplished by the application of an internal acceptor delivery approach. The acceptor, ethanol or monosaccharides, is initially tethered to the fructofuranose 3-hydroxyl group, adjacent to the anomeric center and on the beta-side of the furanose ring, as part of a mixed p-methoxybenzaldehyde acetal, which is formed by DDQ-oxidation of ethyl 1,4,6-tri-O-benzyl-3-O-(4-methoxybenzyl)-2-thio-D-fructofuranoside in the presence of the acceptor or of the p-methoxybenzylated acceptor in the presence of the corresponding 3-OH fructofuranoside. Then, activation of the thioglycoside with a thiophilic promoter allows the delivery of the acceptor from the acetal to the activated anomeric center to yield the beta-linked fructofuranoside in high yields (76-85%). If promoters with nonnucleophilic anions (triflate, perchlorate) are used, the intermediate acetal decomposes to produce the beta-fructofuranoside products as 3-OH derivatives. However, if NIS is used as promoter, the N-succinimide anion interacts with the benzylidene carbon to give the beta-fructofuranoside products as mixed fructofuranoside-3-O-yl N-succinimide p-methoxybenzaldehyde acetals.

  DOI：

  10.1021/jo970983r