ethyl 1,4,6-tri-O-benzyl-2-thio-β-D-fructofuranoside | 178491-60-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 1,4,6-tri-O-benzyl-2-thio-β-D-fructofuranoside
• 英文别名: (2S,3S,4S,5R)-2-ethylsulfanyl-4-phenylmethoxy-2,5-bis(phenylmethoxymethyl)oxolan-3-ol
• CAS: 178491-60-6
• 化学式: C₂₉H₃₄O₅S
• 分子量: 494.652
• InChiKey: GXQIMZJYDJYGCL-GKQHHHCTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  35
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  82.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl 1,4,6-tri-O-benzyl-2-thio-β-D-fructofuranoside 在 4 A molecular sieve 、 sodium hydride 、 DMTST 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 paraffin 为溶剂， 反应 16.5h， 生成 2-(4-nitrophenyl)ethyl 2-azido-4,6-O-benzylidene-2-deoxy-3-O-(1,4,6-tri-O-benzyl-β-D-fructofuranosyl)-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
• 作为产物：
  描述：

  1,4,6-tri-O-benzyl-2,3-O-[1-(benzyloxy)benzylidene]-β-D-fructofuranose 在 calcium sulfate 、 三氟甲磺酸三甲基硅酯 、 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 10.58h， 生成 ethyl 1,4,6-tri-O-benzyl-2-thio-β-D-fructofuranoside
  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

文献信息

• Stereospecific Synthesis of β-<scp>d</scp>-Fructofuranosides Using the Internal Aglycon Delivery Approach
  作者：Christian Krog-Jensen、Stefan Oscarson

  DOI：10.1021/jo960776b

  日期：1996.1.1
• Stereospecific Synthesis of β-<scp>d</scp>-Fructofuranosides Using Thioglycoside Donors and Internal Aglycon Delivery
  作者：Christian Krog-Jensen、Stefan Oscarson

  DOI：10.1021/jo970983r

  日期：1998.3.1

  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.