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-glycero-hex-2-en-4-ulopyranose | 821005-72-5

• 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-β-D-glycero-hex-2-en-4-ulopyranose
• 英文别名: (1R,5R)-3-[(R)-hydroxy-[(2S,3R,4S,5S,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]methyl]-6,8-dioxabicyclo[3.2.1]oct-3-en-2-one
• CAS: 821005-72-5
• 化学式: C₄₁H₄₂O₉
• 分子量: 678.779
• InChiKey: DAMDSSRNXJYUBM-OUXDSXDOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  50
• 可旋转键数：
  15
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  102
• 氢给体数：
  1
• 氢受体数：
  9

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-β-D-glycero-hex-2-en-4-ulopyranose 在 sodium tetrahydroborate 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 3.0h， 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
• 作为产物：
  描述：

  (2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)methanal 、 isolevoglucosenone 在 二乙基碘化铝 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 19.0h， 以73%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-glycero-hex-2-en-4-ulopyranose
  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