2-(trimethylsilyl)ethyl 2,3,6-tri-O-benzyl-4-O-<2,3,6-tri-O-benzyl-4-O-<2,4,6-tri-O-benzyl-3-O-(3,4,6,tri-O-acetyl-2-deoxy-2-phthalimido-β-D-galactopyranosyl)-α-D-galactopyranosyl>-β-D-galactopyranosyl>-β-D-glucopyranoside | 155135-91-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(trimethylsilyl)ethyl 2,3,6-tri-O-benzyl-4-O-<2,3,6-tri-O-benzyl-4-O-<2,4,6-tri-O-benzyl-3-O-(3,4,6,tri-O-acetyl-2-deoxy-2-phthalimido-β-D-galactopyranosyl)-α-D-galactopyranosyl>-β-D-galactopyranosyl>-β-D-glucopyranoside
• 英文别名: 2-(trimethylsilyl)ethyl 2,3,6-tri-O-benzyl-4-O-<2,3,6-tri-O-benzyl-4-O-<2,4,6-tri-O-benzyl-3-O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-galactopyranosyl)-α-D-galactopyranosyl>-β-D-galactopyranosyl>-β-D-glucopyranoside；2-(trimethylsilyl)ethyl 2,3,6-tri-O-benzyl-4-O-<2,3,6-tri-O-benzyl-4-O-<2,4,6-tri-O-benzyl-3-O-(4,6-di-O-acetyl-2-deoxy-2-phthalimido-β-D-galactopyranosyl)-α-D-galactopyranosyl>-β-D-galactopyranosyl>-β-D-glucopyranoside；2-(trimethylsilyl)ethyl 2,3,6-tri-O-benzyl-4-O-{2,3,6-tri-O-benzyl-4-O-[2,4,6-tri-O-benzyl-3-O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-galactopyranosyl)-α-D-galactopyranosyl]-β-D-galactopyranosyl}-β-D-glucopyranoside；[(2R,3R,4R,5R,6S)-3,4-diacetyloxy-6-[(2R,3R,4S,5S,6R)-2-[(2R,3S,4S,5R,6S)-6-[(2R,3R,4S,5R,6R)-4,5-bis(phenylmethoxy)-2-(phenylmethoxymethyl)-6-(2-trimethylsilylethoxy)oxan-3-yl]oxy-4,5-bis(phenylmethoxy)-2-(phenylmethoxymethyl)oxan-3-yl]oxy-3,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-4-yl]oxy-5-(1,3-dioxoisoindol-2-yl)oxan-2-yl]methyl acetate
• CAS: 155135-91-4
• 化学式: C₁₀₆H₁₁₇NO₂₅Si
• 分子量: 1833.17
• InChiKey: XOHKNDHQXQMHCH-FDMJHSOGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  15.65
• 重原子数：
  133
• 可旋转键数：
  48
• 环数：
  15.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  273
• 氢给体数：
  0
• 氢受体数：
  25

反应信息

• 作为反应物：
  描述：

  2-(trimethylsilyl)ethyl 2,3,6-tri-O-benzyl-4-O-<2,3,6-tri-O-benzyl-4-O-<2,4,6-tri-O-benzyl-3-O-(3,4,6,tri-O-acetyl-2-deoxy-2-phthalimido-β-D-galactopyranosyl)-α-D-galactopyranosyl>-β-D-galactopyranosyl>-β-D-glucopyranoside 在 palladium on activated charcoal 氢气 、 溶剂黄146 作用下， 反应 17.0h， 生成
  参考文献：
  名称：

  球四糖四糖和末端三糖和二糖片段的合成。

  摘要：

  球四糖[β-D-GalNAc-（1-> 3）-alpha-D-Gal-（1-> 4）-beta-D-Gal-的2-（三甲基甲硅烷基）乙基（TMSEt）β-糖苷（1-> 4）-D-Glc]和末端三糖，以及末端二糖的甲基α-糖苷1，是由三氟甲磺酸银促进适当保护的半乳糖苷，galabioside和globotrioside的β-糖基化合成的醇与3,4,6-三-O-乙酰基-2-脱氧-2-邻苯二甲酰亚胺基-β-D-吡喃半乳糖苷氯，然后除去保护基。用三氟乙酸-二氯甲烷除去三糖四糖苷和末端三糖的异头TMSEt基团，得到相应的半缩醛糖8和3。末端三糖的TMSEt糖苷通过1-乙酸盐转化，

  DOI：

  10.1016/0008-6215(94)90010-8
• 作为产物：
  描述：

  2-(trimethylsilyl)ethyl 2,3,6-tri-O-benzyl-4-O-<2,3,6-tri-O-benzyl-4-O-(2,4,6-tri-O-benzyl-α-D-galactopyranosyl)-β-D-galactopyranosyl>-β-D-glucopyranoside 、 methyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-1-thio-β-D-galactopyranoside 在 N-碘代丁二酰亚胺 、 molecular sieve 、 三氟甲磺酸 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 1.0h， 以90%的产率得到2-(trimethylsilyl)ethyl 2,3,6-tri-O-benzyl-4-O-<2,3,6-tri-O-benzyl-4-O-<2,4,6-tri-O-benzyl-3-O-(3,4,6,tri-O-acetyl-2-deoxy-2-phthalimido-β-D-galactopyranosyl)-α-D-galactopyranosyl>-β-D-galactopyranosyl>-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of the saccharide moiety of galactosylgloboside (SSEA-3) and its conjugation to bovine serum albumin and sepharose

  摘要：

  The pentasaccharide glycoside corresponding to galactosylgloboside (SSEA-3), beta-D-Gal p-(1 --> 3)-beta-D-Gal pNAc-(1 --> 3)-alpha-D-Gal p-(1 --> 4)-beta-D-Gal p-(1 --> 4)-beta-D-Glc p-1-OCH2CH2Si-(CH3)(3) (4), was synthesized via glycosylation (87%) of 2-(trimethylsilyl)ethyl 2,3,6-tri-O-benzyl-4-O-[2,3 ,6-tri-O-benzyl-4-O-(2,4,6-tri-O-benzyl-alpha-D-galactopyranosyl)-beta-D-galactopyranosyl]-beta-D-glucopyranoside (2) with the glycosyl donor methyl 4,6-di-O-acetyl-2-deoxy-2-phthalimido-3-O-(2,3,4,6-tetra-O-acetyl-beta-D-galactopyranosyl)- 1-thio-beta-D-galactopyranoside (1), followed by removal of protecting groups. Compound 4 was transformed into the spacer glycoside beta-D-Gal p-(1 --> 3)-beta-D-Gal pNAc-(1 --> 3)-alpha-D-Gal p-(1 --> 4)-beta-D-Gal p-(1 --> 4)-beta-D-Glc p-1-SCH2CH2COOH (10), which was coupled to bovine serum albumin (BSA), and Sepharose beads, to give the corresponding neoglycoprotein (11, 6 mol of saccharide/mol of BSA) and glycosylated Sepharose (12, 2.7 mu mol of saccharide/mL of sedimented beads), respectively. An improved synthesis of a protected globotetraoside beta-D-Gal pNAc-(1 --> 3)-alpha-D-Gal p-(1 --> 4)-beta-D-Gal p-(1 --> 4)-beta-D-Glc p-1-OCH(2)CH(2)SiMe(3) is also reported.

  DOI：

  10.1016/0008-6215(95)00044-t

文献信息

• Synthesis of the Forssman pentasaccharide and terminal tetra-, tri-, and di-saccharide fragments
  作者：Ulf Nilsson、Asim K. Ray、Göran Magnusson

  DOI：10.1016/0008-6215(94)90011-6

  日期：1994.1

  The 2-(trimethylsilyl)ethyl (TMSEt) beta-glycosides of the Forssman pentasaccharide [alpha-D-GalNAc-(1-->3)-beta-D-GalNAc-(1-->3)-alpha-D-Gal- (1-->4)-beta-D-Gal-(1-->4)-D-Glc] and the terminal tetrasaccharide, as well as the methyl glycosides 1 and 2 of the terminal di- and tri-saccharides, were synthesised by silver trifluoromethanesulfonate-promoted alpha-glycosylation of suitably protected mono-

  福斯曼五糖[α-D-GalNAc-（1-> 3）-β-D-GalNAc-（1-> 3）-alpha-D-的2-（三甲基甲硅烷基）乙基（TMSEt）β-糖苷Gal-（1-> 4）-beta-D-Gal-（1-> 4）-D-Glc]和末端四糖，以及末端di-和tri-的甲基糖苷1和2通过三氟甲磺酸银促进适当保护的单糖，二糖，三糖和四糖醇与3,4,6-三-O-乙酰基-2-叠氮基-2-脱氧-α-糖基化的α-糖基化反应合成糖D-吡喃半乳糖基溴化物，然后除去保护基。用三氟乙酸-二氯甲烷除去Forssman五糖和末端四糖的异头TMSEt基团，得到相应的半缩醛糖4和6。