2-(trimethylsilyl)ethyl (2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1->3)-(2-acetamido-6-O-4-methoxyphenyl-2-deoxy-β-D-glucopyranosyl)-(1->3)-(2,4,6-tri-O-benzyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside | 1134604-07-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(trimethylsilyl)ethyl (2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1->3)-(2-acetamido-6-O-4-methoxyphenyl-2-deoxy-β-D-glucopyranosyl)-(1->3)-(2,4,6-tri-O-benzyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside
• 英文别名: Bn(-2)[Bn(-3)][Bn(-4)]Fuc(a1-3)[Ph(4-OMe)(-6)]GlcNAc(b1-3)[Bn(-2)][Bn(-4)][Bn(-6)]Gal(b1-4)[Bn(-2)][Bn(-3)][Bn(-6)]Glc(b)-O-EtTMS；N-[(2S,3R,4R,5S,6R)-2-[(2S,3R,4S,5S,6R)-2-[(2R,3R,4S,5R,6R)-4,5-bis(phenylmethoxy)-2-(phenylmethoxymethyl)-6-(2-trimethylsilylethoxy)oxan-3-yl]oxy-3,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-4-yl]oxy-5-hydroxy-6-[(4-methoxyphenoxy)methyl]-4-[(2S,3S,4R,5R,6S)-6-methyl-3,4,5-tris(phenylmethoxy)oxan-2-yl]oxyoxan-3-yl]acetamide
• CAS: 1134604-07-1
• 化学式: C₁₀₁H₁₁₇NO₂₁Si
• 分子量: 1709.12
• InChiKey: IMFPDNBTOWUKFO-QFJUCULBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  15.9
• 重原子数：
  124
• 可旋转键数：
  44
• 环数：
  14.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  225
• 氢给体数：
  2
• 氢受体数：
  21

反应信息

• 作为反应物：
  描述：

  、 2-(trimethylsilyl)ethyl (2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1->3)-(2-acetamido-6-O-4-methoxyphenyl-2-deoxy-β-D-glucopyranosyl)-(1->3)-(2,4,6-tri-O-benzyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside 在 dimethyl(methylthio)sulfonium triflate 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 以61%的产率得到2-(trimethylsilyl)ethyl (methyl 4,7,8,9-tetra-O-acetyl-3,5-dideoxy-5-trifluoroacetamido-D-glycero-α-D-galacto-2-nonulopyranosylonate)-(2->3)-(4,6-di-O-acetyl-2-O-benzoyl-β-D-galactopyranosyl)-(1->4)-[(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1->3)]-(2-acetamido-6-O-4-methoxyphenyl-2-deoxy-β-D-glucopyranosyl)-(1->3)-(2,4,6-tri-O-benzyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside
  参考文献：
  名称：

  Efficient Synthesis of Three Types of Sialyl 6-O-Sulfo Lewis X: Probes for the Comprehensive Search for the Interaction between Carbohydrates and Other Biomoleclues

  摘要：

  Synthesis of three kinds of 6-O-sulfated sLe(x) glyco probes with their relevance to ligand processing pathway of L-selectin has been described. The glycosylation of the suitably protected hexasaccharide acceptor 6 with the sialyl-alpha-(2 -> 3)-D-galactopyranosyl SMe donors (3 and 4) using dimethyl(methylthio)sulfonium triflate (DMTST), afforded the protected tetrasaccharides 7 and 8, respectively. Removal of all the benzyl protecting groups and the subsequent acetylation afforded the sLe(x) derivatives (9 and 10), which were converted to the target compounds (15 and 16) by the selective removal of 4-methoxyphenyl group, followed by 6-O-sulfation of the GlcNAc residue, and removal of all the protective groups under basic conditions. Finally 16 was lactamized with HBTU and HOBT, to give the desired target compound 17.

  DOI：

  10.3987/com-08-s(f)23
• 作为产物：
  描述：

  、 4-甲氧基苯酚 在 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 反应 14.0h， 以70%的产率得到2-(trimethylsilyl)ethyl (2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1->3)-(2-acetamido-6-O-4-methoxyphenyl-2-deoxy-β-D-glucopyranosyl)-(1->3)-(2,4,6-tri-O-benzyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside
  参考文献：
  名称：

  Efficient Synthesis of Three Types of Sialyl 6-O-Sulfo Lewis X: Probes for the Comprehensive Search for the Interaction between Carbohydrates and Other Biomoleclues

  摘要：

  Synthesis of three kinds of 6-O-sulfated sLe(x) glyco probes with their relevance to ligand processing pathway of L-selectin has been described. The glycosylation of the suitably protected hexasaccharide acceptor 6 with the sialyl-alpha-(2 -> 3)-D-galactopyranosyl SMe donors (3 and 4) using dimethyl(methylthio)sulfonium triflate (DMTST), afforded the protected tetrasaccharides 7 and 8, respectively. Removal of all the benzyl protecting groups and the subsequent acetylation afforded the sLe(x) derivatives (9 and 10), which were converted to the target compounds (15 and 16) by the selective removal of 4-methoxyphenyl group, followed by 6-O-sulfation of the GlcNAc residue, and removal of all the protective groups under basic conditions. Finally 16 was lactamized with HBTU and HOBT, to give the desired target compound 17.

  DOI：

  10.3987/com-08-s(f)23

文献信息

• Efficient Synthesis of Three Types of Sialyl 6-O-Sulfo Lewis X: Probes for the Comprehensive Search for the Interaction between Carbohydrates and Other Biomoleclues
  作者：Makoto Kiso、Masanori Yamaguchi、Hideharu Ishida

  DOI：10.3987/com-08-s(f)23

  日期：——

  Synthesis of three kinds of 6-O-sulfated sLe(x) glyco probes with their relevance to ligand processing pathway of L-selectin has been described. The glycosylation of the suitably protected hexasaccharide acceptor 6 with the sialyl-alpha-(2 -> 3)-D-galactopyranosyl SMe donors (3 and 4) using dimethyl(methylthio)sulfonium triflate (DMTST), afforded the protected tetrasaccharides 7 and 8, respectively. Removal of all the benzyl protecting groups and the subsequent acetylation afforded the sLe(x) derivatives (9 and 10), which were converted to the target compounds (15 and 16) by the selective removal of 4-methoxyphenyl group, followed by 6-O-sulfation of the GlcNAc residue, and removal of all the protective groups under basic conditions. Finally 16 was lactamized with HBTU and HOBT, to give the desired target compound 17.