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 | 136520-48-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 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
• CAS: 136520-48-4
• 化学式: C₇₄H₈₇NO₁₆Si
• 分子量: 1274.59
• InChiKey: UQYCSQBIUQOJGO-DMZOCCCTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.04
• 重原子数：
  92
• 可旋转键数：
  30
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.42
• 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：

  溴甲苯 、 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 在 sodium hydride 作用下， 生成 2-(trimethylsilyl)ethyl O-(2-acetamido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-β-D-glucopyranosyl)-(1<*>3)-O-(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：

  合成KDN-乳糖四糖神经酰胺，KDN-神经四糖神经酰胺和KDN-Lewis X神经节苷脂。

  摘要：

  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-

  DOI：

  10.1016/0008-6215(94)84058-x
• 作为产物：
  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

文献信息

• Synthetic Studies on Sialoglycoconjugates 104: Synthesis of Kdn-Lewis X Ganglioside Analogs Containing Modified Reducing Terminal and L-Rhamnose in Place of L-Fucose
  作者：Tomohiro Terada、Hirofumi Simada、Hideharu Ishida、Makoto Kiso、Akira Hasegawa

  DOI：10.1080/07328309808002334

  日期：1998.5.1

  2-(trimethylsilyl)ethyl O-(2,3,4-tri-O-benzyl-α-L-rhamnopyranosyl)-(1→3)-O-(2-acet-amido-6-O-benzyl-2-deoxy-β-D-glucopyranosyl)-(1→3)-O-(2,4,6-tri-O-benzyl-β-D-galactopyranosyl)-(1→4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside (4). The tetrasaccharide 4 was coupled with methyl O-(methyl 4,5,7,8,9-penta-O-acetyl-3-deoxy-D-glycero-α-D-galacto-2-nonulopyranosylonate)-(2→3)-2,4,6-tri-O-benzoyl-1-thio-β-D-galactopyranoside(5)

  KDN-乐X神经节苷脂类似物（10，13，16和19），其含有修饰的还原代替终端和L-鼠李糖L-岩藻糖已被合成。甲基2,3,4-三-O-苄基-1-硫代-α-L-鼠李糖吡喃糖苷（1）与2-（三甲基甲硅烷基）乙基O-（2-乙酰氨基-4,6- O-苄叉基-2） -脱氧-β-D-吡喃葡萄糖基）-（1→3）-O-（2,4,6-三-O-苄基-α-D-半乳糖苷（2），然后将亚苄基乙缩醛还原开环，得到2-（三甲基甲硅烷基）乙基O-（2,3,4-三-O-苄基-α-L-鼠李糖基吡喃糖基）-（1→3）-O-（2-乙酰氨基-6- O-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-吡喃半乳糖基）-（1→4）-2,3,6-三-O-苄基-β-D-吡喃葡萄糖苷（4）。四糖4与甲基O-（甲基4,5,7,8,9-戊-O-乙酰基-3-脱氧-D-甘油-α-D-半乳糖-2-壬基吡喃二磺酸亚磺酸酯）-（2→3）偶联）-2
• 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：——
• KAMEYAMA, AKIHIKO;ISHIDA, HIDEHARU;KISO, MAKOTO;HASEGAWA, AKIRA, CARBOHYDR. RES., 193,(1989) C1-C5
  作者：KAMEYAMA, AKIHIKO、ISHIDA, HIDEHARU、KISO, MAKOTO、HASEGAWA, AKIRA

  DOI：——

  日期：——