n-dodecyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside | 82305-29-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: n-dodecyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside
• 英文别名: n-dodecyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranose；(2S,3R,4S,5R,6R)-2-dodecoxy-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxane
• CAS: 82305-29-1
• 化学式: C₄₆H₆₀O₆
• 分子量: 708.979
• InChiKey: HJIGUVJZURGYDF-PSKPMRIASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.1
• 重原子数：
  52
• 可旋转键数：
  25
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  n-dodecyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 144.0h， 生成 十二烷基 alpha-D-吡喃葡萄糖苷
  参考文献：
  名称：

  Effect of Anomeric Linkage on the Sialylation of Glycosides by Cells

  摘要：

  The synthesis of sialylated glycosides using saccharide primers and cells was investigated. alpha center dot and beta center dot Saccharide primers were chemically synthesized and introduced into B16 melanoma cells to prime oligosaccharide synthesis. Incorporation of alpha- and beta-dodecyl lactosides into B16 cells resulted in the sialylation of the galactose residue to give GM3-type oligosaccharides. The beta-dodecyl galactoside primer was sialylated but the alpha-dodecyl galactoside primer was not. Both the alpha- and beta-dodecyl glucoside primers were not elongated. In the glycosylation of primers by cells, this research confirmed that sialyl transferases tolerate acceptor modifications and are permissive to primer elongation regardless of the alpha- or beta-linkage to the aglycon unit. However, the presence of the terminal galactose residue that is beta-linked to the adjacent saccharide or aglycon unit is essential for sialylation by cellular enzymes to occur.

  DOI：

  10.1080/07328300500208107
• 作为产物：
  描述：

  2,3,4,6-tetra-O-benzyl-1-O-[N-allyl-thiocarbamoyl]-D-glucopyranose 、 十二烷醇 在 溴 、 碳酸氢钠 、 lithium fluoride 作用下， 以 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.17h， 以88%的产率得到n-dodecyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside
  参考文献：
  名称：

  Kasprzycka; Szeja, Polish Journal of Chemistry, 2005, vol. 79, # 2, p. 329 - 333

  摘要：

  DOI：

文献信息

• A Stereoselective One-stage α-Glucosylation with 2,3,4,6-Tetra-<i>O</i>-benzyl-α-D-glucopyranose and a Mixture of Methanesulfonic Acid, Cobalt(II) Bromide, and Tetraethylammonium Perchlorate
  作者：Shinkiti Koto、Naohiko Morishima、Shonosuke Zen

  DOI：10.1246/bcsj.55.1543

  日期：1982.5

  A one-stage procedure for the stereoselective α-glucosylation of alcohol with 2,3,4,6-tetra-O-benzyl-α-D-glucopyranose and a mixture of methanesulfonic acid, cobalt(II) bromide, and tetraethylammonium perchlorate is described. The mechanism of the glucosylation reaction is discussed.

  醇与 2,3,4,6-四-O-苄基-α-D-吡喃葡萄糖和甲磺酸、溴化钴 (II) 和四乙基高氯酸铵的混合物的立体选择性 α-葡萄糖基化的一步程序是描述。讨论了糖基化反应的机理。
• Effect of Anomeric Linkage on the Sialylation of Glycosides by Cells
  作者：Maria Carmelita Z. Kasuya、Maki Ikeda、Kazuhiko Hashimoto、Toshinori Sato、Kenichi Hatanaka

  DOI：10.1080/07328300500208107

  日期：2005.9.1

  The synthesis of sialylated glycosides using saccharide primers and cells was investigated. alpha center dot and beta center dot Saccharide primers were chemically synthesized and introduced into B16 melanoma cells to prime oligosaccharide synthesis. Incorporation of alpha- and beta-dodecyl lactosides into B16 cells resulted in the sialylation of the galactose residue to give GM3-type oligosaccharides. The beta-dodecyl galactoside primer was sialylated but the alpha-dodecyl galactoside primer was not. Both the alpha- and beta-dodecyl glucoside primers were not elongated. In the glycosylation of primers by cells, this research confirmed that sialyl transferases tolerate acceptor modifications and are permissive to primer elongation regardless of the alpha- or beta-linkage to the aglycon unit. However, the presence of the terminal galactose residue that is beta-linked to the adjacent saccharide or aglycon unit is essential for sialylation by cellular enzymes to occur.
• Kasprzycka; Szeja, Polish Journal of Chemistry, 2005, vol. 79, # 2, p. 329 - 333
  作者：Kasprzycka、Szeja

  DOI：——

  日期：——