(2R,3R,4R,5R,6R)-2-methoxy-5-phenylmethoxy-6-(phenylmethoxymethyl)-4-[(R)-phenylmethoxy-[(2S,3R,4S,5S,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]methyl]oxan-3-ol | 821005-92-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3R,4R,5R,6R)-2-methoxy-5-phenylmethoxy-6-(phenylmethoxymethyl)-4-[(R)-phenylmethoxy-[(2S,3R,4S,5S,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]methyl]oxan-3-ol
• CAS: 821005-92-9
• 化学式: C₆₃H₆₈O₁₁
• 分子量: 1001.23
• InChiKey: WWFRZTLLNVHYRL-VRYDZKEHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.1
• 重原子数：
  74
• 可旋转键数：
  26
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  溴甲苯 、 (2R,3R,4R,5R,6R)-2-methoxy-5-phenylmethoxy-6-(phenylmethoxymethyl)-4-[(R)-phenylmethoxy-[(2S,3R,4S,5S,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]methyl]oxan-3-ol 在 四丁基碘化铵 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 以26 mg的产率得到methyl 2,4,6-tri-O-benzyl-3-C-[(1R)-1,3,4,5,7-penta-O-benzyl-2,6-anhydro-D-glycero-L-manno-heptitol-1-C-yl]-3-deoxy-D-galacto-pyranoside
  参考文献：
  名称：

  Synthesis of C-linked analogues of β-d-galactopyranosyl-(1→3)-d-galactopyranosides and of β-d-galactopyranosyl-(1→3)-d-galactal

  摘要：

  C-linked disaccharide derivatives mimicking O-beta-D-galactopyranosyl-(1-->3)-D-galactopyranosides (end groups in Core-B structures of biologically important proteoglycans) have been obtained from isolevoglucosenone and beta-D-galactopyranosylcarbaldehyde derivatives. The beta-D-galactopyranosyl-(1-->3)-CH(OH)-D-galactal derivatives 3a (4,6-di-O-acetyl-3-C-[(1R)-1,3,4,5,7-penta-O-acetyl-2,6-anhydro-D-glycero-mannno-heptitol-1-C-yl]-3-deoxy-D-galactal), 3b (4,6-di-O-benzyl-3-C-[(1R)-2,6-anhydro-1,3,4,5,7-penta-O-benzyl-D-glycerocero-L-manno-heptitol-1-C-yl]-3-deoxy-D-galactal) and the beta-D-galactopyranosyl-(1-->3)-CH2-D-galactal 3c (4,6-O-diacetyl-3-C-) [6-O-acetyl-2,3,4-tri-O-(tert-butyl)dimethylsilyl-beta-D-galactopyranosyl-methyl]-3-deoxy-D-galactal have been prepared. One of them, 3a, has been shown to be a suitable agent for the O-glycosidation and the construction of glycoconjugates bearing the beta-D-Galp-(1-->3)-CH(OH)-D-Galp-O moiety. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.09.029
• 作为产物：
  描述：

  甲醇 、 4,6-di-O-benzyl-3-C-[(1R)-1,3,4,5,7-penta-O-benzyl-2,6-anhydro-D-glycero-L-manno-heptitol-1-C-yl]-3-deoxy-D-galactal 在 二甲基二环氧乙烷 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 5.5h， 生成 (2R,3R,4R,5R,6R)-2-methoxy-5-phenylmethoxy-6-(phenylmethoxymethyl)-4-[(R)-phenylmethoxy-[(2S,3R,4S,5S,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]methyl]oxan-3-ol
  参考文献：
  名称：

  Synthesis of C-linked analogues of β-d-galactopyranosyl-(1→3)-d-galactopyranosides and of β-d-galactopyranosyl-(1→3)-d-galactal

  摘要：

  C-linked disaccharide derivatives mimicking O-beta-D-galactopyranosyl-(1-->3)-D-galactopyranosides (end groups in Core-B structures of biologically important proteoglycans) have been obtained from isolevoglucosenone and beta-D-galactopyranosylcarbaldehyde derivatives. The beta-D-galactopyranosyl-(1-->3)-CH(OH)-D-galactal derivatives 3a (4,6-di-O-acetyl-3-C-[(1R)-1,3,4,5,7-penta-O-acetyl-2,6-anhydro-D-glycero-mannno-heptitol-1-C-yl]-3-deoxy-D-galactal), 3b (4,6-di-O-benzyl-3-C-[(1R)-2,6-anhydro-1,3,4,5,7-penta-O-benzyl-D-glycerocero-L-manno-heptitol-1-C-yl]-3-deoxy-D-galactal) and the beta-D-galactopyranosyl-(1-->3)-CH2-D-galactal 3c (4,6-O-diacetyl-3-C-) [6-O-acetyl-2,3,4-tri-O-(tert-butyl)dimethylsilyl-beta-D-galactopyranosyl-methyl]-3-deoxy-D-galactal have been prepared. One of them, 3a, has been shown to be a suitable agent for the O-glycosidation and the construction of glycoconjugates bearing the beta-D-Galp-(1-->3)-CH(OH)-D-Galp-O moiety. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.09.029