2-(trimethylsilyl)ethyl 2,3,4-tri-O-benzoyl-β-D-galactopyranoside | 231616-32-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(trimethylsilyl)ethyl 2,3,4-tri-O-benzoyl-β-D-galactopyranoside
• 英文别名: [(2R,3S,4S,5R,6R)-4,5-dibenzoyloxy-2-(hydroxymethyl)-6-(2-trimethylsilylethoxy)oxan-3-yl] benzoate
• CAS: 231616-32-3
• 化学式: C₃₂H₃₆O₉Si
• 分子量: 592.718
• InChiKey: ARMZKYBCZHXUQD-IUBCVFBCSA-N

物化性质

• 沸点：
  685.7±55.0 °C(predicted)
• 密度：
  1.25±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.74
• 重原子数：
  42
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  118
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2-(trimethylsilyl)ethyl 2,3,4-tri-O-benzoyl-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：

  2-(三甲基硅烷基)乙基beta-吡喃半乳糖苷 在 吡啶 、 咪唑 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 13.0h， 生成 2-(trimethylsilyl)ethyl 2,3,4-tri-O-benzoyl-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

文献信息

• Synthesis of oligomeric phosphono analogues of Leishmania lipophosphoglycan fragments
  作者：Vladimir S. Borodkin、Fiona C. Milne、Michael A.J. Ferguson、Andrei V. Nikolaev

  DOI：10.1016/s0040-4039(02)01588-5

  日期：2002.10

  A set of isosteric phosphono (C-glycoside) analogues of Leishmania lipophosphoglycan fragments have been synthesised by making use of a sequence of uniformly stereoselective glycosylation reactions of phosphono-oligosaccharide glycosyl acceptors with phosphono-oligosaccharide thioglycosides.

  利什曼原虫脂磷酸糖片段的一组等排膦酰基（C-糖苷）类似物已通过利用膦酰基-寡糖糖基受体与膦酰基-低聚糖硫糖苷的均匀立体选择性糖基化反应序列而合成。
• Synthetic Studies on Glycosphingolipids from Protostomia Phyla: Synthesis of Neogala-Series Glycolipid Analogues Containing a Mannose Residue from the Earthworm Pheretima hilgendorfi.
  作者：Noriyasu HADA、Akiko MATSUSAKI、Mutsumi SUGITA、Tadahiro TAKEDA

  DOI：10.1248/cpb.47.1265

  日期：——

  Two kinds of glycosphingolipid analogues from the earthworm Pheretima hilgendorfi were synthesized as follows : the trisaccharide 2-(tetradecyl)hexadecyl α-D-mannopyranosyl-(1→4)-β-D-galactopyranosyl-(1→6)-β-D-galactopyranoside (13) and the tetrasaccharide 2-(tetradecyl) hexadecyl α-D-galactopyranosyl-(1→6)-[α-D-mannopyranosyl-(1→4)]-β-D-galactopyranosyl-(1→6)-β-D-galactpyranoside (20) were synthesized by stepwise condensation of suitably protected monosaccharide units. A 2-(trimethylsilyl)ethyl 2, 3, 4-tri-O-benzoyl-β-D-galactopyranoside derivative (5) was used as the glycosyl acceptor and thiophenyl derivatives of D-galactose and D-mannose were used as donors respectively.

  从蚯蚓 Pheretima hilgendorfi 中合成了以下两种糖磷脂类似物：三糖 2-(十四烷基)十六烷基 α-D-吡喃甘露糖基-(1→4)-β-D-吡喃半乳糖基-(1→6)-β-D-吡喃半乳糖苷 (13) 和四糖 2-(十四烷基)十六烷基 α-D-半乳糖苷-(1→6)-[α-D-吡喃甘露糖基-(1→4)]-β-D-吡喃半乳糖苷-(1→6)-β-D-吡喃半乳糖苷(20)是通过逐步缩合适当保护的单糖单元合成的。2-(trimethylsilyl)ethyl 2, 3, 4-tri-O-benzoyl-β-D-galactopyranoside 衍生物 (5) 用作糖基受体，D-半乳糖和 D-甘露糖的硫代苯衍生物分别用作供体。
• Synthesis of potential bisubstrate inhibitors of Leishmania elongating α-d-mannosyl phosphate transferase
  作者：Vladimir S. Borodkin、Michael A.J. Ferguson、Andrei V. Nikolaev

  DOI：10.1016/j.tetlet.2003.11.022

  日期：2004.1

  Synthesis of a potential mechanism-based bisubstrate inhibitor 1 of the elongating alpha-D-mannosyl phosphate transferase in Leishmania, comprising a guanosine subunit bound to the synthetic acceptor substrate through the methylenebisphosphonate linker, as well as its analogues 2 and 3 has been successfully accomplished. (C) 2003 Elsevier Ltd. All rights reserved.
• Synthetic studies on glycosphingolipids from Protostomia phyla: syntheses and biological activities of amphoteric glycolipids containing a phosphocholine residue from the earthworm Pheretima hilgendorfi
  作者：Noriyasu Hada、Yukihiko Shida、Hiroshi Shimamura、Yoshiko Sonoda、Tadashi Kasahara、Mutsumi Sugita、Tadahiro Takeda

  DOI：10.1016/j.carres.2008.05.001

  日期：2008.9

  Two types of amphoteric glycosphingolipid found in the earthworm Pheretima hilgendorfi, PC(-> 6)-beta-D-Galp-(1 -> 6)-beta-D-Galp-(1 -> 1)Cer (1) and PC(-> 6)-beta-D-Galp-(1 -> 6)-beta-D-Galp-(1 -> 6)-beta-D-Galp-(1 -> 1)Cer (2), and their derivatives (4, 5) were synthesized. These were examined for their ability to enhance production of interleukin-8 (IL-8), a potent inflammatory cytokine involved in neutrophil chemotaxis, in a TNF alpha-stimulated granulocytic HL-60 cells. Compounds 1 and 2 were found to be potent enhancers of IL-8 production. (C) 2008 Elsevier Ltd. All rights reserved.
• Glycosidation Reactions of Benzyl-Type Selenoglycoside Donors
  作者：Hiromune Ando、Makoto Kiso、Masanori Menjo、Hideki Tamai、Hideharu Ishida、Mamoru Koketsu

  DOI：10.3987/com-13-s(s)99

  日期：——

  p-Methoxybenzyl (PMB), and p-nitrobenzyl (PNB) selenoglycosides of glucose were synthesized, and their glycosidation reactions were investigated. The Bn and PNB derivatives were successfully activated with IBr-AgClO4 to provide the glycosylated products in high yields. The glycosidation with the PMB derivatives required promotion with a metal triflate, such as (CuOTf)(2).PhMe or In(OTf)(3), and afforded the glycosylated products in medium to high yields.