1,6-anhydro-3-C-[(1R)-2,6-anhydro-3,4,5,7-tetra-O-benzyl-D-glycero-L-manno-heptitol-1-C-yl]-2,3-dideoxy-2-phenylthio-β-D-galacto-pyranose | 821005-74-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,6-anhydro-3-C-[(1R)-2,6-anhydro-3,4,5,7-tetra-O-benzyl-D-glycero-L-manno-heptitol-1-C-yl]-2,3-dideoxy-2-phenylthio-β-D-galacto-pyranose
• 英文别名: (1R,2R,3R,4R,5R)-3-[(R)-hydroxy-[(2S,3R,4S,5S,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]methyl]-4-phenylsulfanyl-6,8-dioxabicyclo[3.2.1]octan-2-ol
• CAS: 821005-74-7
• 化学式: C₄₇H₅₀O₉S
• 分子量: 790.975
• InChiKey: KODOUZPRTIFMHV-YUDSUGQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  57
• 可旋转键数：
  17
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  130
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  1,6-anhydro-3-C-[(1R)-2,6-anhydro-3,4,5,7-tetra-O-benzyl-D-glycero-L-manno-heptitol-1-C-yl]-2,3-dideoxy-2-phenylthio-β-D-galacto-pyranose 在 镍 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以87%的产率得到1,6-anhydro-3-C-[(1R)-2,6-anhydro-3,4,5,7-tetra-O-benzyl-D-glycero-L-manno-heptitol-1-C-yl]-2,3-dideoxy-β-D-lyxo-hexopyranose
  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：

  isolevoglucosenone 在 sodium tetrahydroborate 、 二乙基碘化铝 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 22.0h， 生成 1,6-anhydro-3-C-[(1R)-2,6-anhydro-3,4,5,7-tetra-O-benzyl-D-glycero-L-manno-heptitol-1-C-yl]-2,3-dideoxy-2-phenylthio-β-D-galacto-pyranose
  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

文献信息

• Synthesis of C-linked analogues of β-d-galactopyranosyl-(1→3)-d-galactopyranosides and of β-d-galactopyranosyl-(1→3)-d-galactal
  作者：Raynald Demange、Loay Awad、Pierre Vogel

  DOI：10.1016/j.tetasy.2004.09.029

  日期：2004.11

  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.