2-(trimethylsilyl)ethyl (3,4,6-tri-O-acetyl-2-acetamido-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 | 205813-52-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(trimethylsilyl)ethyl (3,4,6-tri-O-acetyl-2-acetamido-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: GlcNAc3Ac4Ac6Ac(b1-3)[Bn(-2)][Bn(-4)][Bn(-6)]Gal(b1-4)[Bn(-2)][Bn(-3)][Bn(-6)]Glc(b)-O-EtTMS；[(2R,3S,4R,5R,6S)-5-acetamido-3,4-diacetyloxy-6-[(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]oxyoxan-2-yl]methyl acetate
• CAS: 205813-52-1
• 化学式: C₇₃H₈₉NO₁₉Si
• 分子量: 1312.59
• InChiKey: DCPXMTLMUIXPOL-JNLHKJCCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.99
• 重原子数：
  94
• 可旋转键数：
  36
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  219
• 氢给体数：
  1
• 氢受体数：
  19

反应信息

• 作为反应物：
  描述：

  2-(trimethylsilyl)ethyl (3,4,6-tri-O-acetyl-2-acetamido-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 sodium methylate 、 对甲苯磺酸 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 2.17h， 生成 N-[(4aR,6S,7R,8R,8aS)-6-[(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-8-hydroxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-yl]acetamide
  参考文献：
  名称：

  Synthesis of Sialyl-α-(2→3)-Neolactotetraose Derivatives Containing Different Sialic Acids: Molecular Probes for Elucidation of Substrate Specificity of Human α1,3-Fucosyltransferases

  摘要：

  A series of sialyl-alpha-(2-->3)-neolactotetraose derivatives containing N-acetyl-(NeuAc), N-glycolyl- (NeuGc) and N-butanoylneuraminic acid, and 3-deoxy-D-glycero-D-galacto-2-nonulosonic acid (KDN) have systematically been synthesized as molecular probes for elucidation of substrate specificity of human alpha 1,3-fucosyltransferases (Fuc-TVII and Fuc-TVI). 2-Methyl-(3,4, 6-tri-O-acetyl-1,2-dideoxy-alpha-D-glucopylano)-[2',1' :4,5]-2-oxazoline (1) was coupled with 2-(trimethyl-silyl)-ethyl (2,4,6-tri-O-benzyl-beta-D-galactopyranosyl) -(1 --> 4)-2,3,6-tri-O-benzyl-beta-D-glucopyranoside (2) to give a trisaccharide 3 which, upon successive O-deacetylation, benzylidenation and reductive opening of the benzylidene group, afforded a common glycosyl acceptor 5. Glycosylation of 5 with sialyl-alpha-(2-->3)-galactose donors 6-8, 19 and 21 gave the corresponding pentasaccharides 22-25, which were converted to a series of sialyl-alpha-(2-->3)-neolactotetraose derivatives 30-33. In the competitive enzyme assay, the NeuGc derivative 32 showed the most potent activity for Fuc-TVII, while the KDN derivative 31 was less active than the standard NeuAc derivative 30. In contrast, the N-butanoylation of neuraminic acid enhanced the activity for Fuc-TVI.

  DOI：

  10.1080/07328300008544114
• 作为产物：
  描述：

  2-(trimethylsilyl)ethyl (2,4,6-tri-O-benzyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-galactopyranoside 、 (3aR)-2-甲基-5alpha-(乙酰氧基甲基)-6beta,7alpha-二乙酰氧基-3Aalpha,6,7,7Aalpha-四氢-5H-吡喃并[3,2-d]恶唑 在 molecular sieve 、 对甲苯磺酸 作用下， 以 1,2-二氯乙烷 为溶剂， 以60%的产率得到2-(trimethylsilyl)ethyl (3,4,6-tri-O-acetyl-2-acetamido-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：

  Synthesis of a Neolactotetraose Glycoside Suitable for Enzymatic Elaboration to the Sialyl Lewis X Stage

  摘要：

  A tetrasaccharide glycoside comprising the core of the sialyl Lewis X structure was synthesized from "building-block" derivatives of the component sugar units. Initially 2-methyl-(3,4,6-tri-O-acetyl-1,2-dideoxy-alpha-D-glucopyrano)-[2',1':4,5]-2-oxazoline (1) was coupled to the known 2-(trimethylsilyl) ethyl 2,3,6,2',4',6'-hexa-O-benzyl-beta-D-lactoside to give a trisaccharide glycoside (3) in 60% yield. De-O-acetylation, benzylidenation, benzylation, and reductive opening of the benzylidene acetal function of 6 gave a derivative having OH-4" open. This derivative was coupled with tetra-O-acetyl-alpha-D-galactosyl bromide to give a tetrasaccharide in 62% yield, and the product was de-O-acetylated and de-O-benzylated to give the target compound, 2-(trimethylsilyl)ethyl beta-D-galactopyranosyl-(1-->4)-2-acetamido-2-deoxy-beta-D-glucopyranosyl-(1-->3)-beta-D-galactopyranosyl-(1-->4)-beta-D-glucopyranoside (11).

  DOI：

  10.1080/07328309808002327