phenyl 6-O-benzyl-2-deoxy-2-phthalimido-4-O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-1-thio-β-D-glucopyranoside | 227749-87-3

• 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: phenyl 6-O-benzyl-2-deoxy-2-phthalimido-4-O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-1-thio-β-D-glucopyranoside
• 英文别名: [(2R,3S,4S,5R,6S)-3,4,5-tribenzoyloxy-6-[(2R,3S,4R,5R,6S)-5-(1,3-dioxoisoindol-2-yl)-4-hydroxy-2-(phenylmethoxymethyl)-6-phenylsulfanyloxan-3-yl]oxyoxan-2-yl]methyl benzoate
• CAS: 227749-87-3
• 化学式: C₆₁H₅₁NO₁₅S
• 分子量: 1070.14
• InChiKey: IPNMHFCWMWXQBX-WWEDBSIGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.9
• 重原子数：
  78
• 可旋转键数：
  22
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  225
• 氢给体数：
  1
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  1-硫-乙基-2,3,4-三-氧-苄基-b-L-硫代呋喃岩藻糖苷 、 phenyl 6-O-benzyl-2-deoxy-2-phthalimido-4-O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-1-thio-β-D-glucopyranoside 在 N-碘代丁二酰亚胺 、 三氟甲磺酸 、 4 Angstroem MS 作用下， 以 甲苯 为溶剂， 反应 0.17h， 以86%的产率得到phenyl 6-O-benzyl-2-deoxy-2-phthalimido-4-O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-1-thio-3-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of the β-Methyl Glycoside of Lacto-N-Fucopentaose III

  摘要：

  A total synthesis of the beta-methyl glycoside of lacto-N-fucopentaose III (1) is described. Phenyl 2,3,4,6-tetra-O-benzoyl-beta-D-galactopyranosyl-(1-->4)-6-O-benzyl-2-deoxy-2-phthalimido-1-thio-beta-D-glucopyranoside (4), a key intermediate prepared by condensation of 2,3,4,6-tetra-O-benzoyl-alpha-D-galactopyranosyl bromide (2) and phenyl 6-O-benzyl-2-deoxy-2-phthalimido-1-thio-beta-D-glucopyranoside (3), was glycosylated with ethyl 2,3,4-tri-O-benzyl-1-thio-beta-L-fucopyranoside (5) to give the trisaccharide donor 6, which, on coupling with methyl 2,6-di-O-benzyl-beta-D-galactopyranosyl-(1-->4)2,3,6-tri-O-benzyl-beta-D-glucopyranoside (7), afforded the pentasaccharide 8. It was easily transformed into the target pentasaccharide 1 via hydrazinolysis, acetylation, O-deacetylation, and hydrogenolysis.

  DOI：

  10.1080/07328309908544006
• 作为产物：
  描述：

  2,3,4,6-tetra-O-benzoyl-α-D-galactopyranosyl bromide 、 phenyl 6-O-benzyl-2-deoxy-2-phthalimido-1-thio-1-deoxy-β-D-glucopyranoside 在 silver trifluoromethanesulfonate 作用下， 以 二氯甲烷 为溶剂， 以78%的产率得到phenyl 6-O-benzyl-2-deoxy-2-phthalimido-4-O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  NMR study of a LewisX pentasaccharide derivative: solution structure and interaction with cations

  摘要：

  The structure and conformation of the synthetic pentasaccharide Gal(beta 1-4){Fuc(alpha 1-3)}GlcNAc(beta 1-3)Gal(beta 1-4)Glc-beta OMe of the Lewis(x) family has been determined by NMR spectroscopy in dimethyl sulfoxide and methanol. In these solvents, the binding constants with calcium have been evaluated as 9.5 and 29.6 M-1, respectively. Study of the interaction sites has been achieved through the use of paramagnetic divalent cations and distance triangulation methods. Two regions have been found, the first one in the vicinity of the fucose unit, the second one closer to the lactose part. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(98)00301-2

文献信息

• Synthetic sulfated glucuronosyl paragloboside (SGPG) and its use for the detection of autoimmune peripheral neuropathies
  作者：Reynald Chevalier、Benoît Colsch、Carlos Afonso、Nicole Baumann、Jean-Claude Tabet、Jean-Maurice Mallet

  DOI：10.1016/j.tet.2005.10.021

  日期：2006.1

  The sulfated glucuronosyl paragloboside SO4-3-GlcA(beta 1-3)Gal-(beta 1-4)GlcNAc(beta 1-3)Gal-(beta 1-4)Glc beta(1-1')Cer (SGPG) is a specific constituent of the peripheral nervous system involved in human dysimmune neuropathies. Although it is highly immunogenic in human pathology, it is not a major constituent of peripheral nerve in humans. Pure SGPG is very difficult to obtain from natural sources, but is needed for the design of efficient and reproducible immunoassays. We describe a new chemical synthesis of this important glycolipid with a stearic tail, including its complete characterization by mass spectrometry and its use in the detection of autoimmune neuropathies. (c) 2005 Elsevier Ltd. All rights reserved.
• Synthesis and NMR study of a heptasaccharide, epitope of the stage-specific embryonic antigen-1 (SSEA-1)
  作者：Yongmin Zhang、Bruno Dausse、Pierre Sinaÿ、Mohamed Afsahi、Patrick Berthault、Hervé Desvaux

  DOI：10.1016/s0008-6215(99)00299-2

  日期：2000.3

  This paper describes an efficient synthesis of the beta-2-trimethylsilylethyl glycoside of lacto-N-fucoheptaose based on a highly stereo- and regioselective glycosylation between a Lewis(x) trisaccharidic donor and a tetraol tetrasaccharidic acceptor. The title compound was characterized by high-resolution NMR spectroscopy. (C) 2000 Elsevier Science Ltd. All rights reserved.
• NMR study of a LewisX pentasaccharide derivative: solution structure and interaction with cations
  作者：Benoı̂t Henry、Hervé Desvaux、Marina Pristchepa、Patrick Berthault、Yong-Min Zhang、Jean-Maurice Mallet、Jacques Esnault、Pierre Sinaÿ

  DOI：10.1016/s0008-6215(98)00301-2

  日期：1999.1

  The structure and conformation of the synthetic pentasaccharide Gal(beta 1-4)Fuc(alpha 1-3)}GlcNAc(beta 1-3)Gal(beta 1-4)Glc-beta OMe of the Lewis(x) family has been determined by NMR spectroscopy in dimethyl sulfoxide and methanol. In these solvents, the binding constants with calcium have been evaluated as 9.5 and 29.6 M-1, respectively. Study of the interaction sites has been achieved through the use of paramagnetic divalent cations and distance triangulation methods. Two regions have been found, the first one in the vicinity of the fucose unit, the second one closer to the lactose part. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Synthesis of the β-Methyl Glycoside of Lacto-<i>N</i>-Fucopentaose III
  作者：Yong-Min Zhang、Jacques Esnault、Jean-Maurice Mallet、Pierre Sinaÿ

  DOI：10.1080/07328309908544006

  日期：1999.1

  A total synthesis of the beta-methyl glycoside of lacto-N-fucopentaose III (1) is described. Phenyl 2,3,4,6-tetra-O-benzoyl-beta-D-galactopyranosyl-(1-->4)-6-O-benzyl-2-deoxy-2-phthalimido-1-thio-beta-D-glucopyranoside (4), a key intermediate prepared by condensation of 2,3,4,6-tetra-O-benzoyl-alpha-D-galactopyranosyl bromide (2) and phenyl 6-O-benzyl-2-deoxy-2-phthalimido-1-thio-beta-D-glucopyranoside (3), was glycosylated with ethyl 2,3,4-tri-O-benzyl-1-thio-beta-L-fucopyranoside (5) to give the trisaccharide donor 6, which, on coupling with methyl 2,6-di-O-benzyl-beta-D-galactopyranosyl-(1-->4)2,3,6-tri-O-benzyl-beta-D-glucopyranoside (7), afforded the pentasaccharide 8. It was easily transformed into the target pentasaccharide 1 via hydrazinolysis, acetylation, O-deacetylation, and hydrogenolysis.