phenyl 2,4-di-O-acetyl-3-O-benzyl-6-O-(tert-butyldimethylsilyl)-1-thio-β-D-galactopyranoside | 231616-37-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 2,4-di-O-acetyl-3-O-benzyl-6-O-(tert-butyldimethylsilyl)-1-thio-β-D-galactopyranoside
• 英文别名: Bn(-3)[TBDMS(-6)]Gal2Ac4Ac(b)-SPh；[(2R,3S,4S,5R,6S)-5-acetyloxy-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-4-phenylmethoxy-6-phenylsulfanyloxan-3-yl] acetate
• CAS: 231616-37-8
• 化学式: C₂₉H₄₀O₇SSi
• 分子量: 560.784
• InChiKey: ZLDSTKFFHMXCBM-JYIVOWJTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.97
• 重原子数：
  38
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  106
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  phenyl 2,4-di-O-acetyl-3-O-benzyl-6-O-(tert-butyldimethylsilyl)-1-thio-β-D-galactopyranoside 在 palladium on activated charcoal 吡啶 、 N-碘代丁二酰亚胺 、 三氟甲磺酸 、 4 A molecular sieve 、 氢气 、 溶剂黄146 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 DMTST 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 20.83h， 生成 2,3,4-tri-O-acetyl-α-L-fucopyranosyl-(1->3)-2,4,6-tri-O-acetyl-β-D-galactopyranosyl-(1->6)-2,3,4-tri-O-benzoyl-α-D-galactopyranosyl trichloroacetimidate
  参考文献：
  名称：

  Synthetic studies on glycosphingolipids from the parasite Echinococcus multilocularis

  摘要：

  Novel neutral glycosphingolipids isolated from the metacestodes of Echinococcus multilocularis by Persat, may be expected to be involved in host-parasite interactions. We have synthesized these glycosphingolipid analogues containing 2-branched fatty alkyl residues in place of ceramide. The glycosylation of galactosyl donors 4 and 5 with each of the accepters 2 and 11 in the presence of N-iodosuccinimide (NIS)/TfOH, and the glycosylation of fucosyl donor 13 with accepters 12 and 20 in the presence of dimethyl(methylthio)sulfonium triflate (DMTST) gave the desired oligosaccharide derivatives at good yield. The fully per-O-acylated 2-(trimethylsilyl)ethyl glycosides 6, 15, 21, and 26 were converted to glycosylimidates 7, 16, 22, and 27, which were condensed with 2-(tetradecyl)hexadecanol and subsequently deacylated give four target glycosphingolipid analogues. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(99)00027-0
• 作为产物：
  描述：

  phenyl 3-O-benzyl-1-thio-β-D-galactopyranoside 在 吡啶 、 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 生成 phenyl 2,4-di-O-acetyl-3-O-benzyl-6-O-(tert-butyldimethylsilyl)-1-thio-β-D-galactopyranoside
  参考文献：
  名称：

  Synthetic studies on glycosphingolipids from the parasite Echinococcus multilocularis

  摘要：

  Novel neutral glycosphingolipids isolated from the metacestodes of Echinococcus multilocularis by Persat, may be expected to be involved in host-parasite interactions. We have synthesized these glycosphingolipid analogues containing 2-branched fatty alkyl residues in place of ceramide. The glycosylation of galactosyl donors 4 and 5 with each of the accepters 2 and 11 in the presence of N-iodosuccinimide (NIS)/TfOH, and the glycosylation of fucosyl donor 13 with accepters 12 and 20 in the presence of dimethyl(methylthio)sulfonium triflate (DMTST) gave the desired oligosaccharide derivatives at good yield. The fully per-O-acylated 2-(trimethylsilyl)ethyl glycosides 6, 15, 21, and 26 were converted to glycosylimidates 7, 16, 22, and 27, which were condensed with 2-(tetradecyl)hexadecanol and subsequently deacylated give four target glycosphingolipid analogues. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(99)00027-0