methyl O-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-(1->4)-3,6-di-O-benzyl-β-D-glucopyranoside | 303966-48-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl O-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-(1->4)-3,6-di-O-benzyl-β-D-glucopyranoside
• 英文别名: methyl 3,6-di-O-benzyl-4-O-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-β-D-glucopyranoside；Bn(-2)[Bn(-3)][Bn(-4)][Bn(-6)]Gal(b1-4)[Bn(-3)][Bn(-6)]b-Glc1Me；(2R,3R,4R,5R,6R)-2-methoxy-4-phenylmethoxy-6-(phenylmethoxymethyl)-5-[(2S,3R,4S,5S,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxyoxan-3-ol
• CAS: 303966-48-5
• 化学式: C₅₅H₆₀O₁₁
• 分子量: 897.075
• InChiKey: BQGMYCKYBOXWEA-MNMINXCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  66
• 可旋转键数：
  23
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  113
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  methyl O-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-(1->4)-3,6-di-O-benzyl-β-D-glucopyranoside 在 草酰氯 、 二甲基亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 0.67h， 生成
  参考文献：
  名称：

  Synthesis of the Tetrasaccharide Cap Domain of the Antigenic Lipophosphoglycan of Leishmania donovani Parasite

  摘要：

  In this paper we report a new synthesis of the immunologically important tetrasaccharide terminal cap domain [Galp(1--4)-beta[Manp-( 1-2)-alpha-Manp-(1-2)-alpha]-Manp] of lipophosphoglycan (LPG); the major cell surface GPI molecule and key virulence factor of the protozoan parasite Leishmania donovani. The synthetic approach provided a short convergent route for the LPG cap motif from lactose and mannose starting materials. The synthesis was then applied for the preparation of a radiolabelled cap epitope for macrophage receptor binding and immunological studies. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00609-8
• 作为产物：
  描述：

  hexa-O-benzyl lactal 在 2,2-dimethyl dioxirane 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 6.0h， 生成 methyl O-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-(1->4)-3,6-di-O-benzyl-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of the Tetrasaccharide Cap Domain of the Antigenic Lipophosphoglycan of Leishmania donovani Parasite

  摘要：

  In this paper we report a new synthesis of the immunologically important tetrasaccharide terminal cap domain [Galp(1--4)-beta[Manp-( 1-2)-alpha-Manp-(1-2)-alpha]-Manp] of lipophosphoglycan (LPG); the major cell surface GPI molecule and key virulence factor of the protozoan parasite Leishmania donovani. The synthetic approach provided a short convergent route for the LPG cap motif from lactose and mannose starting materials. The synthesis was then applied for the preparation of a radiolabelled cap epitope for macrophage receptor binding and immunological studies. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00609-8

文献信息

• Epoxidation of glycals with oxone–acetone–tetrabutylammonium hydrogen sulfate: a convenient access to simple β-d-glycosides and to α-d-mannosamine and d-talosamine donors
  作者：Dominique Lafont、Joseph D’Attoma、Rejane Gomez、Peter G. Goekjian

  DOI：10.1016/j.tetasy.2011.06.027

  日期：2011.6

  The addition of a phase transfer catalyst during the epoxidation of perbenzylated glycals with oxone-acetone under biphasic conditions allows their complete epoxidation. The epoxides were readily transformed into methyl 1,2-trans-beta-D-glycosides or 1,2-trans-beta-D-glycopyranosyl azides (D-gluco and-D-galacto configurations) bearing a free hydroxyl group at the 2-position. These glycosyl azides were converted to alkyl 1,2-trans-2-acetamido-2-deoxy-alpha-D-pyranosides or alkyl 2-allyloxycarbonylamino-2deoxy-alpha-D-pyranosides (D-manno and D-talo configurations) by a Staudinger reaction and a double inversion of configuration at C-1 and C-2. (C) 2011 Elsevier Ltd. All rights reserved.
• Synthesis of the Tetrasaccharide Cap Domain of the Antigenic Lipophosphoglycan of Leishmania donovani Parasite
  作者：Mani Upreti、Dipali Ruhela、Ram A Vishwakarma

  DOI：10.1016/s0040-4020(00)00609-8

  日期：2000.8

  In this paper we report a new synthesis of the immunologically important tetrasaccharide terminal cap domain [Galp(1--4)-beta[Manp-( 1-2)-alpha-Manp-(1-2)-alpha]-Manp] of lipophosphoglycan (LPG); the major cell surface GPI molecule and key virulence factor of the protozoan parasite Leishmania donovani. The synthetic approach provided a short convergent route for the LPG cap motif from lactose and mannose starting materials. The synthesis was then applied for the preparation of a radiolabelled cap epitope for macrophage receptor binding and immunological studies. (C) 2000 Elsevier Science Ltd. All rights reserved.