2-(trimethylsilyl)ethyl (2-acetamido-3,6-di-O-benzyl-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 | 160711-39-7

• 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-acetamido-3,6-di-O-benzyl-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(-3)[Bn(-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-4-phenylmethoxy-6-(phenylmethoxymethyl)oxan-3-yl]acetamide
• CAS: 160711-39-7
• 化学式: C₈₁H₉₅NO₁₆Si
• 分子量: 1366.73
• InChiKey: OQKQTXQYMUNEJK-ZQVKIBANSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.73
• 重原子数：
  99
• 可旋转键数：
  36
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  179
• 氢给体数：
  2
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  2-(trimethylsilyl)ethyl (2-acetamido-3,6-di-O-benzyl-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 、 2,3,4,6-四乙酰氧基-alpha-D-吡喃糖溴化物 在 氰化汞 作用下， 以 硝基甲烷 、 苯 为溶剂， 反应 16.0h， 以62%的产率得到2-(trimethylsilyl)ethyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-2-acetamido-3,6-di-O-benzyl-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
• 作为产物：
  描述：

  在 盐酸 、 molecular sieve 、 sodium cyanoborohydride 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 0.25h， 以72%的产率得到2-(trimethylsilyl)ethyl (2-acetamido-3,6-di-O-benzyl-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

文献信息

• Synthesis of KDN-lactotetraosylceramide, KDN-neolactotetraosylceramide, and KDN-Lewis X ganglioside
  作者：Tomohiro Terada、Makoto Kiso、Akira Hasegawa

  DOI：10.1016/0008-6215(94)84058-x

  日期：1994.6

  ne. Glycosylation of 2-(trimethylsilyl)ethyl O-(2-acetamido-4,6-O-benzylidene-2-deoxy-beta-D-glucopyranosyl)-(1-->3)- O- (2,4,6-tri-O-benzyl-beta-D-galactopyranosyl)-(1-->4)-2,3,6-tri-O-benzyl- beta- D-glucopyranoside (5) or of 2-(trimethylsilyl)ethyl O-(2-acetamido-3,6-di-O-benzyl-2-deoxy-beta-D-glucopyranosyl)-(1-->3)-O- (2,4,6-tri-O-benzyl-beta-D-galactopyranosyl)-(1-->4)-2,3,6-tri-O-benzyl- beta-

  唾液酸基-乳基四糖基神经酰胺，唾液酸基-新四糖基神经酰胺和唾液酸化的路易斯X神经节苷脂的类似物，其中N-乙酰基神经氨酸残基被3-脱氧-D-甘油-D-半乳糖-2-壬基吡喃二磺酸（KDN）单元取代已合成。O-（4,5,7,8,9-戊基-O-乙酰基-3-脱氧-D-甘油-α-D-半乳糖-2-壬基吡喃二磺酸甲酯）-（2-> 3）-2，由2-（三甲基甲硅烷基）乙基O-（甲基4,5,7,8,9-五-O-乙酰基-3-脱氧-D-甘油-α-D-半乳糖-2-壬基吡喃二磺酸根）-（2-> 3）-6-O-苯甲酰基-β-D-吡喃半乳糖苷，通过O-苯甲酰化，取代2- （三甲基甲硅烷基）乙基被乙酰基取代，并与三甲基（甲硫基）硅烷一起引入甲硫基。2-（三甲基甲硅烷基）乙基O-（2-乙酰氨基-4）的糖基化 6-O-亚苄基-2-脱氧-β-D-吡喃葡萄糖基）-（1→3）-O-（2,4,6-三-O-苄基-β-D-吡喃并吡喃糖基）-（1-
• Synthesis of Lacto‐ and Neolacto‐series Ganglioside Analogs Containing <i>N</i>‐Glycolylneuraminic Acid: Probes for Investigation of Specific Receptor Structures Recognized by Influenza A Viruses
  作者：Kyoko Fukunaga、Tsuyoshi Toyoda、Hideharu Ishida、Makoto Kiso

  DOI：10.1081/car-120026602

  日期：2003.12.31

  Sialic acids are essential components of host‐cell surface receptors for infection of influenza virus. To investigate the specific receptor structures recognized by various influenza A viruses, a series of lacto‐ and neolacto‐series ganglioside analogs containing N‐glycolylneuraminic acid (Neu5Gc) have been synthesized. The pentasaccharide structures of Neu5Gc‐α‐(2→3)/(2→6)‐lactotetraose (IV3(6)Neu5GcLcOse)

  唾液酸是感染流感病毒的宿主细胞表面受体的重要组成部分。为了研究各种甲型流感病毒识别的特定受体结构，已合成了一系列含有N-羟乙酰神经氨酸（Neu5Gc）的乳酸和新乳糖系列神经节苷脂类似物。Neu5Gc-α-（2→3）/（2→6）-乳糖四糖（IV3（6）Neu5GcLcOse）和Neu5Gc-α-（2→3）/（2→6）-乳清四糖（IV3（6 ）Neu5GcnLcOse）是通过分别用Neu5Gc-α-（2→3）/（2→6）-Gal三氯乙酰亚氨酸盐供体（1和21）对适当保护的三糖受体（2A和2B）进行糖基化而构建的。在4、11、23，将三氯乙亚氨酸酯组中的30和30分别提供了一系列Neu5Gc-α-（2→3）/（2→6）-乳糖和新乳糖四糖供体（7、13、26和33），并与2-（十四烷基）偶联。十六烷醇（8），得到相应的糖脂（9、14、27和34）。最后，完全除去O-酰基和将甲基酯基皂化得到所需的神
• Synthetic Studies on Sialoglycoconjugates 90: Total Synthesis of Sulfated Glucuronyl Paraglobosides
  作者：Yukihiro Isogai、Tomoko Kawase、Hideharu Ishida、Makoto Kiso、Akira Hasegawa

  DOI：10.1080/07328309608005705

  日期：1996.11

  stereocontrolled glycosidation, methyl (4-O-acetyl-2-O-benzoyl-3-O-levulinoyl-α-D-glucopyranosyl trichloroacetimidate)uronate (8) was prepared from methyl [2-(trimethylsilyl)ethyl β-D-glucopyranosid]uronate (3) via selective 4-O-acetylation, 2-O-benzoylation, 3-O-levulinoylation, removal of the 2-(trimethylsilyl)ethyl group and imidate formation. The glycosylation of 8 with 2-(trimethylsilyl)ethyl 2,4,6-tri-O-

  已经合成了3- O-磺基葡萄糖醛酸酰基副球糖苷衍生物（五糖）。设计用于在最后一步有效，立体控制苷化的简便的硫酸化重要的中间体，甲基（4- ø -乙酰基-2- ø -苯甲酰基-3- ö -levulinoyl-α-d吡喃葡糖基三氯乙酰亚胺酯）糖醛酸（8）为由[2-（三甲基甲硅烷基）乙基β-D-吡喃葡萄糖苷]尿酸酯（3）经选择性的4- O-乙酰化，2- O-苯甲酰化，3- O-乙酰丙酰化，去除2-（三甲基甲硅烷基）乙基制备和亚氨酸盐的形成。8的糖基化用三甲基甲硅烷基三氟甲磺酸酯与2-（三甲基甲硅烷基）乙基2,4,6-三-O-苄基-β-D-吡喃半乳糖苷（9）得到2-（三甲基甲硅烷基）乙基O-（甲基4 - O-乙酰基-2- O -苯甲酰基-3- O-乙酰丙酰基-β-D-吡喃葡萄糖基尿酸酯）-（1→3）-2,4,6-三-O-苄基-β-D-吡喃半乳糖苷（10），通过除去苄基，苯甲酰化，去除2-（三甲基
• Synthesis of Sialyl-α-(2→3)-Neolactotetraose Derivatives Containing Different Sialic Acids: Molecular Probes for Elucidation of Substrate Specificity of Human α1,3-Fucosyltransferases
  作者：Eiji Tanahashi、Kyoko Fukunaga、Yuko Ozawa、Tsuyoshi Toyoda、Hidcharu Ishida、Makoto Kiso

  DOI：10.1080/07328300008544114

  日期：2000.1

  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.
• Terada, Tomohiro; Ishida, Hideharu; Kiso, Makoto, Journal of Carbohydrate Chemistry, 1995, vol. 14, # 6, p. 751 - 768
  作者：Terada, Tomohiro、Ishida, Hideharu、Kiso, Makoto、Hasegawa, Akira

  DOI：——

  日期：——