1,2,3,4-tetra-O-acetyl-6-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-D-galactopyranose | 887700-91-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1,2,3,4-tetra-O-acetyl-6-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-D-galactopyranose
• 英文别名: Bn(-2)[Bn(-3)][Bn(-4)][Bn(-6)]Gal(a1-6)Gal1Ac2Ac3Ac4Ac；[(2R,3S,4S,5R)-4,5,6-triacetyloxy-2-[[(2S,3R,4S,5S,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxymethyl]oxan-3-yl] acetate
• CAS: 887700-91-6
• 化学式: C₄₈H₅₄O₁₅
• 分子量: 870.948
• InChiKey: CVYGDKKDJAABMT-ORGMWGKGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  63
• 可旋转键数：
  24
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  170
• 氢给体数：
  0
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  1,2,3,4-tetra-O-acetyl-6-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-D-galactopyranose 在 苄胺 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 以70%的产率得到Acetic acid (2R,3S,4S,5R)-4,5-diacetoxy-6-hydroxy-2-((2S,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxymethyl)-tetrahydro-pyran-3-yl ester
  参考文献：
  名称：

  Syntheses of an α-d-Gal-(1→6)-β-d-Gal diglyceride, as lipase substrate

  摘要：

  Two different routes were explored to afford 3-O-(6-0-alpha-D-galactopyranosyl-beta-D-galactopyranosyl)-1,2-di-O-dodecanoyl-sn-glycerol. In the first one, the key step was the glycosylation of the 3-O-(2,3,4-tri-O-benzyl-beta-D-galactopyranosyl)- 1, 2-O-isopropylidene-sn-glycerol acceptor with 2-pyridyl 2,3,4,6-tetra-O-benzyl-1-thio-beta-D-galactopyranoside as the donor. In the second one, the key step was the coupling of 2,3,4-tri-O-acetyl-6-O-(2,3,4,6-tetra-O-benzyl-alpha-D-galactopyranosyl)-D-galactopyranosyl trichloroacetimidate donor with 1,2-O-isopropylidene-sn-glycerol. Even though the number of steps was the same in both pathways, the first one afforded a better overall yield (12.4%) than the second one (6.5%). This eight-step synthesis allowed the preparation of the expected glycolipid, which was used as substrate for recombinant GPLRP2 galactolipase using the monomolecular film technique. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.01.021
• 作为产物：
  描述：

  6-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-1,2:3,4-di-O-isopropylidene-D-galactopyranose 、 乙酸酐 在 吡啶 作用下， 以 水 、 三氟乙酸 为溶剂， 反应 0.5h， 以62%的产率得到1,2,3,4-tetra-O-acetyl-6-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-D-galactopyranose
  参考文献：
  名称：

  Syntheses of an α-d-Gal-(1→6)-β-d-Gal diglyceride, as lipase substrate

  摘要：

  Two different routes were explored to afford 3-O-(6-0-alpha-D-galactopyranosyl-beta-D-galactopyranosyl)-1,2-di-O-dodecanoyl-sn-glycerol. In the first one, the key step was the glycosylation of the 3-O-(2,3,4-tri-O-benzyl-beta-D-galactopyranosyl)- 1, 2-O-isopropylidene-sn-glycerol acceptor with 2-pyridyl 2,3,4,6-tetra-O-benzyl-1-thio-beta-D-galactopyranoside as the donor. In the second one, the key step was the coupling of 2,3,4-tri-O-acetyl-6-O-(2,3,4,6-tetra-O-benzyl-alpha-D-galactopyranosyl)-D-galactopyranosyl trichloroacetimidate donor with 1,2-O-isopropylidene-sn-glycerol. Even though the number of steps was the same in both pathways, the first one afforded a better overall yield (12.4%) than the second one (6.5%). This eight-step synthesis allowed the preparation of the expected glycolipid, which was used as substrate for recombinant GPLRP2 galactolipase using the monomolecular film technique. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.01.021

文献信息

• Immunostimulatory activities of monoglycosylated α-d-pyranosylceramides
  作者：Akira Uchimura、Toshiyuki Shimizu、Masahiro Morita、Hitomi Ueno、Kazuhiro Motoki、Hideaki Fukushima、Takenori Natori、Yasuhiko Koezuka

  DOI：10.1016/s0968-0896(97)00169-7

  日期：1997.12

  We compared the immunostimulatory effects of chemically synthesized alpha-galactosylceramides (alpha-GalCers), alpha-glucosylceramides (alpha-GluCers), 6 "-monoglycosylated alpha-GalCer and 6 "- or 4 "-monoglycosylated alpha-GluCer and made the following observations: (1) the length of the fatty acid side chain in the ceramide portions greatly affects the immunostimulatory effects of alpha-GalCers and alpha-GluCers; (2) the configuration of the 4 "-hydroxyl group of the inner pyranose moiety plays an important role in the immunostimulatory effects of monoglycosylated alpha-D-pyranosylceramides; (3) the free 4 "-hydroxyl group of the inner pyranose of monoglycosylated alpha-D-pyranosylceramides plays a more important role in their immunostimulatory effects than the free 6 "-hydroxyl group. (C) 1997 Elsevier Science Ltd.