dodecyl 2,3,4-tri-O-benzyl-1-thio-β-L-fucopyranoside | 1138457-36-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: dodecyl 2,3,4-tri-O-benzyl-1-thio-β-L-fucopyranoside
• 英文别名: (2R,3S,4R,5R,6S)-2-dodecylsulfanyl-6-methyl-3,4,5-tris(phenylmethoxy)oxane
• CAS: 1138457-36-9
• 化学式: C₃₉H₅₄O₄S
• 分子量: 618.921
• InChiKey: HCTCQQXKXGGITN-DQTCGZRCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.9
• 重原子数：
  44
• 可旋转键数：
  21
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  62.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  dodecyl 2,3,4-tri-O-benzyl-1-thio-β-L-fucopyranoside 、 methyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->3)-6-O-benzyl-2-deoxy-2-phthalimido-α-D-glucopyranoside 在 2,6-二叔丁基-4-甲基吡啶 、 1-(苯基亚硫酰基)哌啶 、 三氟甲磺酸酐 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以85%的产率得到methyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->3)-[2,3,4-tri-O-benzyl-α-L-fucopyranosyl-(1->4)]-6-O-benzyl-2-deoxy-2-phthalimido-α-D-glucopyranoside
  参考文献：
  名称：

  Pre-activation of fully acetylated dodecyl thioglycosides with BSP–Tf2O led to efficient glycosylation at low temperature

  摘要：

  Fully acetylated dodecyl thioglycosides were found to be useful as glycosyl donors by activation with 1-benzenesulfinyl piperidine (BSP) and triflic anhydride (Tf2O) at -78 degrees C. The glycosyl acceptor was added to the reaction mixture at the same temperature to furnish various disaccharide, including the protected Lewis a (Le(a)) trisaccharide, in good yields. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2008.11.008
• 作为产物：
  描述：

  (2R,3S,4R,5S,6S)-2-dodecylsulfanyl-6-methyloxane-3,4,5-triol 、 溴甲苯 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 以1.9 g的产率得到dodecyl 2,3,4-tri-O-benzyl-1-thio-β-L-fucopyranoside
  参考文献：
  名称：

  Pre-activation of fully acetylated dodecyl thioglycosides with BSP–Tf2O led to efficient glycosylation at low temperature

  摘要：

  Fully acetylated dodecyl thioglycosides were found to be useful as glycosyl donors by activation with 1-benzenesulfinyl piperidine (BSP) and triflic anhydride (Tf2O) at -78 degrees C. The glycosyl acceptor was added to the reaction mixture at the same temperature to furnish various disaccharide, including the protected Lewis a (Le(a)) trisaccharide, in good yields. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2008.11.008

文献信息

• Synthetic construction of a fucosyl chitobiose as an allergen-associated carbohydrate epitope and the glycopolymer involving highly clustered trisaccharidic sequences
  作者：Koji Matsuoka、Hiroki Yamaguchi、Tetsuo Koyama、Ken Hatano、Daiyo Terunuma

  DOI：10.1016/j.tetlet.2010.03.004

  日期：2010.5

  Synthetic construction of fucosyl chitobiose [GlcNAc beta 1 -> 4(Fuc alpha 1 -> 3)GlcNAc] as an allergy-associated carbohydrate epitope was accomplished from three building blocks. The trisaccharidic unit was further transformed into a carbohydrate monomer and polymerization of the glycomonomer proceeded smoothly to provide a series of glycopolymers having various carbohydrate densities. In addition to the organic syntheses, biological evaluations of the glycomonomer and the polymers were carried out and sugar-clustering effects were observed. (C) 2010 Elsevier Ltd. All rights reserved.
• Pre-activation of fully acetylated dodecyl thioglycosides with BSP–Tf2O led to efficient glycosylation at low temperature
  作者：Sang-Hyun Son、Chiharu Tano、Tetsuya Furuike、Nobuo Sakairi

  DOI：10.1016/j.carres.2008.11.008

  日期：2009.2

  Fully acetylated dodecyl thioglycosides were found to be useful as glycosyl donors by activation with 1-benzenesulfinyl piperidine (BSP) and triflic anhydride (Tf2O) at -78 degrees C. The glycosyl acceptor was added to the reaction mixture at the same temperature to furnish various disaccharide, including the protected Lewis a (Le(a)) trisaccharide, in good yields. (C) 2008 Elsevier Ltd. All rights reserved.