2-(trimethylsilyl)ethyl <2,3-bis-O-(phenylmethyl)-β-D-galactopyranosyl>-(1,4)-2,3,6-tris-O-(phenylmethyl)-β-D-glucopyranoside | 164525-86-4

• 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-bis-O-(phenylmethyl)-β-D-galactopyranosyl>-(1,4)-2,3,6-tris-O-(phenylmethyl)-β-D-glucopyranoside
• 英文别名: 2-(Trimethylsilyl)ethyl O-(2,3-di-O-benzyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside；Bn(-2)[Bn(-3)]Gal(b1-4)[Bn(-2)][Bn(-3)][Bn(-6)]Glc(b)-O-EtTMS；(2R,3S,4S,5R,6S)-6-[(2R,3R,4S,5R,6R)-4,5-bis(phenylmethoxy)-2-(phenylmethoxymethyl)-6-(2-trimethylsilylethoxy)oxan-3-yl]oxy-2-(hydroxymethyl)-4,5-bis(phenylmethoxy)oxan-3-ol
• CAS: 164525-86-4
• 化学式: C₅₂H₆₄O₁₁Si
• 分子量: 893.159
• InChiKey: OFLHURNEKGAENZ-FFDPGXBPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.09
• 重原子数：
  64
• 可旋转键数：
  23
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  124
• 氢给体数：
  2
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  2-(trimethylsilyl)ethyl <2,3-bis-O-(phenylmethyl)-β-D-galactopyranosyl>-(1,4)-2,3,6-tris-O-(phenylmethyl)-β-D-glucopyranoside 、 (2R,3S,4R,5S,6R)-4-Acetoxy-5-acetylamino-3-(2,4-dimethyl-phenylsulfanyl)-2-methylsulfanyl-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester 在 2,6-二叔丁基吡啶 、 silver trifluoromethanesulfonate 、 二异丙胺 、 苯次磺酰氯 作用下， 生成 2-(trimethylsilyl)ethyl 2,3,6-tri-O-benzyl-4-O-[2,3-di-O-benzyl-6-O-(methyl-{5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-3-[(2,4-dimethylphenyl)thio]-D-erythro-α-L-gluco-2-nonulopyranosid}onate)-β-D-galactopyranosyl]-β-D-glucopyranoside
  参考文献：
  名称：

  A Practical Method for the Synthesis of Sialyl α-Glycosides

  摘要：

  Addition of 2,4-dimethylbenzenesulfenyl chloride to sialic acid glycal gives crystalline 2-chloro-3-thiosialic acid 3 in 85% yield. Reaction of 3 with sodium thiomethoxide in acetonitrile at 0 degrees C affords the sialic acid donor alpha-2-(methylthio)-3-thiosialic acid 4 in quantitative yield. Sialylation of glycosyl accepters 9 and 10 with 4 in the presence of phenylsulfenyl triflate (PST) as promotor in CH3CN at -40 degrees C gives alpha-sialosides in good yield and excellent stereoselectivity. No beta-sialosides are formed in either case. Removal of the auxiliary 3-(2,4-dimethylphenyl)-thio group is achieved in high yield using Ph(3)SnH and AIBN in refluxing toluene. Protected GM(3) trisaccharide and 6-sial-2-yllactose were obtained on a gram scale.

  DOI：

  10.1021/ja960148b
• 作为产物：
  描述：

  2-(三甲基硅烷基)乙基乳糖苷 在 sodium hydride 、 对甲苯磺酸 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 2-(trimethylsilyl)ethyl <2,3-bis-O-(phenylmethyl)-β-D-galactopyranosyl>-(1,4)-2,3,6-tris-O-(phenylmethyl)-β-D-glucopyranoside
  参考文献：
  名称：

  N-羟甲基神经氨酸（NeuGc的有效供体）的甲基2-硫代糖苷的简便制备物

  摘要：

  由N-乙酰神经氨酸（NeuAc）分6步合成N-乙酰神经氨酸（SMe-NeuGc，1）的甲基2-硫代糖苷（SMe-NeuGc，1），它是NeuGc在制备唾液酸糖结合物中的有效供体。1可以用两个乳糖受体糖基化以高产率得到唾液酸寡糖8、9和10。

  DOI：

  10.1016/0040-4039(96)00383-8

文献信息

• Hotta, Kenji; Itoh, Ken-ichi; Kameyama, Akihiko, Journal of Carbohydrate Chemistry, 1995, vol. 14, # 1, p. 115 - 134
  作者：Hotta, Kenji、Itoh, Ken-ichi、Kameyama, Akihiko、Ishida, Hideharu、Kiso, Makoto、Hasegawa, Akira

  DOI：——

  日期：——
• A Practical Method for the Synthesis of Sialyl α-Glycosides
  作者：Valeri Martichonok、George M. Whitesides

  DOI：10.1021/ja960148b

  日期：1996.1.1

  Addition of 2,4-dimethylbenzenesulfenyl chloride to sialic acid glycal gives crystalline 2-chloro-3-thiosialic acid 3 in 85% yield. Reaction of 3 with sodium thiomethoxide in acetonitrile at 0 degrees C affords the sialic acid donor alpha-2-(methylthio)-3-thiosialic acid 4 in quantitative yield. Sialylation of glycosyl accepters 9 and 10 with 4 in the presence of phenylsulfenyl triflate (PST) as promotor in CH3CN at -40 degrees C gives alpha-sialosides in good yield and excellent stereoselectivity. No beta-sialosides are formed in either case. Removal of the auxiliary 3-(2,4-dimethylphenyl)-thio group is achieved in high yield using Ph(3)SnH and AIBN in refluxing toluene. Protected GM(3) trisaccharide and 6-sial-2-yllactose were obtained on a gram scale.
• A facile preparation of the methyl 2-thioglycoside of N-glycolylneuraminic acid, an efficient donor of NeuGc
  作者：Tetsuji Sugata、Ryuichi Higuchi

  DOI：10.1016/0040-4039(96)00383-8

  日期：1996.4

  The methyl 2-thioglycoside of N-glycolylneuraminic acid (SMe-NeuGc, 1), which is an efficient donor of NeuGc in the preparation of sialosyl glycoconjugates, was synthesized from N-acetylneuraminic acid (NeuAc) in 6 steps in good yield. 1 could be glycosylated with two lactose acceptors to give sialosyl oligosaccharides 8, 9 and 10 in high yields.

  由N-乙酰神经氨酸（NeuAc）分6步合成N-乙酰神经氨酸（SMe-NeuGc，1）的甲基2-硫代糖苷（SMe-NeuGc，1），它是NeuGc在制备唾液酸糖结合物中的有效供体。1可以用两个乳糖受体糖基化以高产率得到唾液酸寡糖8、9和10。