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 | 155135-83-4

• 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-α-D-galactopyranosyl)-β-D-galactopyranosyl>-β-D-glucopyranoside
• 英文别名: Bn(-2)[Bn(-4)][Bn(-6)]Gal(a1-4)[Bn(-2)][Bn(-3)][Bn(-6)]Gal(b1-4)[Bn(-2)][Bn(-3)][Bn(-6)]Glc(b)-O-EtTMS；(2R,3R,4S,5R,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-ol
• CAS: 155135-83-4
• 化学式: C₈₆H₉₈O₁₆Si
• 分子量: 1415.8
• InChiKey: AWRKLGZMTJHVFW-VLUIRWEZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.81
• 重原子数：
  103
• 可旋转键数：
  38
• 环数：
  12.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  159
• 氢给体数：
  1
• 氢受体数：
  16

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-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
• 作为产物：
  描述：

  2-(trimethylsilyl)ethyl 4-O-<4-O-(3-O-allyl-2,4,6-tri-O-benzyl-α-D-galactopyranosyl)-2,3,6-tri-O-benzyl-β-D-galactopyranosyl>-2,3,6-tri-O-benzyl-β-D-glucopyranoside 在 palladium dichloride 作用下， 以 甲醇 为溶剂， 反应 2.67h， 以75%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-α-D-galactopyranosyl)-β-D-galactopyranosyl>-β-D-glucopyranoside
  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

文献信息

• Synthesis of the globotetraose tetrasaccharide and terminal tri- and di-saccharide fragments
  作者：Ulf Nilsson、Asim K. Ray、Göran Magnusson

  DOI：10.1016/0008-6215(94)90010-8

  日期：1994.1

  groups. Removal of the anomeric TMSEt group of the globotetraoside and of the terminal trisaccharide, using trifluoroacetic acid-dichloromethane, gave the corresponding hemiacetal sugars 8 and 3. The TMSEt glycoside of the terminal trisaccharide was converted, via the 1-acetate, into the corresponding isobutyl (4) and 3-butylsulfonyl-2-[(butylsulfonyl)methyl]propyl (5) glycosides and into the TMSEt thioglycoside

  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，
• Synthesis of the saccharide moiety of galactosylgloboside (SSEA-3) and its conjugation to bovine serum albumin and sepharose
  作者：Ulf Nilsson、Göran Magnusson

  DOI：10.1016/0008-6215(95)00044-t

  日期：1995.7

  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.