methyl (phenyl 5-acetoxyacetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycero-D-galacto-2-nonulopyranoside)onate | 299179-54-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl (phenyl 5-acetoxyacetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycero-D-galacto-2-nonulopyranoside)onate
• 英文别名: methyl [phenyl 5-acetoxyacetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycero-D-galacto-non-2-ulopyranosid]onate
• CAS: 299179-54-7
• 化学式: C₂₈H₃₅NO₁₄S
• 分子量: 641.65
• InChiKey: QCPNULREWMEXEY-NMWMJRCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.84
• 重原子数：
  44.0
• 可旋转键数：
  13.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  196.13
• 氢给体数：
  1.0
• 氢受体数：
  15.0

反应信息

• 作为反应物：
  描述：

  methyl (phenyl 5-acetoxyacetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycero-D-galacto-2-nonulopyranoside)onate 在 4-二甲氨基吡啶 、 N-碘代丁二酰亚胺 、 三氟甲磺酸 、 3 A molecular sieve 作用下， 以 吡啶 、 乙腈 为溶剂， 反应 21.0h， 生成 2-(trimethylsilyl)ethyl O-(methyl 5-acetoxyacetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonate)-(2->3)-2,4,6-tri-O-benzoyl-β-D-galactopyranoside
  参考文献：
  名称：

  Synthesis of a Sialyl Lewis X Ganglioside Analogue ContainingN-Glycolyl in Place of theN-Acetyl Group in theN-Acetylneuraminic Acid Residue

  摘要：

  合成了一种含有 5-甘氨酰氨基-3,5-二脱氧-D-甘油-D-半乳糖-2-nonulopyranosylonic 酸而不是 N-acetylneurarninic 酸的 sialyl Lewis X 神经节苷脂类似物，明确了选择素识别中对 sialic 酸分子中 N-acetyl 基团的结构要求。

  DOI：

  10.1271/bbb.59.1091
• 作为产物：
  描述：

  苯硫酚 、 methyl (5-acetoxyacetamido-2,4,7,8,9-penta-O-acetyl-3,5-dideoxy-D-glycero-D-galacto-2-nonulopyranosyl)onate 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以87%的产率得到methyl (phenyl 5-acetoxyacetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycero-D-galacto-2-nonulopyranoside)onate
  参考文献：
  名称：

  Synthesis of a Sialyl Lewis X Ganglioside Analogue ContainingN-Glycolyl in Place of theN-Acetyl Group in theN-Acetylneuraminic Acid Residue

  摘要：

  合成了一种含有 5-甘氨酰氨基-3,5-二脱氧-D-甘油-D-半乳糖-2-nonulopyranosylonic 酸而不是 N-acetylneurarninic 酸的 sialyl Lewis X 神经节苷脂类似物，明确了选择素识别中对 sialic 酸分子中 N-acetyl 基团的结构要求。

  DOI：

  10.1271/bbb.59.1091

文献信息

• 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
• 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.
• Sialylation using N-glycolylneuraminyl phosphite donors to synthesize Neu5Gc-containing glycans
  作者：Shinya Hanashima、Taku Tomiya、Daichi Ishikawa、Shoji Akai、Ken-ichi Sato

  DOI：10.1016/j.carres.2009.03.004

  日期：2009.5

  Efficient sialylations using N-glycolylneuraminic acid (Neu5Gc) phosphite donors having an acetyl or benzyl group on the glycolyl moiety are described in the synthesis of Neu5Gc-containing glycans. Both phosphite donors 1 and 2 were readily coupled with primary and secondary acceptor alcohols in propionitrile at -78 degrees C to provide the desired glycosides with good alpha-selectivities. (C) 2009 Elsevier Ltd. All rights reserved.
• Preparative route to N-glycolylneuraminic acid phenyl 2-thioglycoside donor and synthesis of Neu5Gc-α-(2→3′)-lactosamine 3-aminopropyl glycoside
  作者：Andrei A. Sherman、Olga N. Yudina、Alexander S. Shashkov、Vladimir M. Menshov、Nikolay E. Nifantiev

  DOI：10.1016/s0008-6215(02)00003-4

  日期：2002.3

  The spacer-armed trisaccharide, Neu5Ge-alpha-(2-->3')-lactosamine 3-aminopropyl glycoside, was synthesized by regio- and stereoselective sialylation of the suitably protected triol acceptor. 3-trifluoroacetamidopropyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-4-O-(6-O-benzyl-beta-D-galactopyranosyl)-beta-D-glucopyranoside, with the donor methyl [phenyl 5-acetoxyacetamido-4.7,8.9-tetra-O-acetyl-3.5-dideoxy-2-thio-D-glycero-alpha,beta-D-galacto-2-nonulopyranosid]onate. The donor was obtained. in turn, from methyl [phenyl 5-acetamido-4,7,8.9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycero-alpha,beta-D-galacto-2-nonulopyranosid]onate by N-tert-butoxycarbonylation of the acetamido group followed by total N- and O-deacetylation, per-O-acetylation, subsequent Boc group removal, and N-acetoxyacetylation. (C) 2002 Elsevier Science Ltd. All rights reserved.