(1'S,2'S)-ethyl 2-O-[2-O-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)-6-O-benzoyl-3O,4O-(1',2'-dimethoxycyclohexan-1',2'-diyl)-α-D-mannopyranosyl]-6-O-benzoyl-3O,4O-(1',2'-dimethoxycyclohexan-1',2'-diyl)-1-thio-α-D-mannopyranoside | 171192-40-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1'S,2'S)-ethyl 2-O-[2-O-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)-6-O-benzoyl-3O,4O-(1',2'-dimethoxycyclohexan-1',2'-diyl)-α-D-mannopyranosyl]-6-O-benzoyl-3O,4O-(1',2'-dimethoxycyclohexan-1',2'-diyl)-1-thio-α-D-mannopyranoside
• 英文别名: [(1S,3R,4R,6R,7S,8S,10S)-6-[[(1S,3R,4R,6R,7S,8S,10S)-4-(benzoyloxymethyl)-6-ethylsulfanyl-1,10-dimethoxy-2,5,9-trioxatricyclo[8.4.0.03,8]tetradecan-7-yl]oxy]-1,10-dimethoxy-7-[(2R,3S,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxy-2,5,9-trioxatricyclo[8.4.0.03,8]tetradecan-4-yl]methyl benzoate
• CAS: 171192-40-8
• 化学式: C₇₈H₉₂O₂₁S
• 分子量: 1397.64
• InChiKey: AOXQRKHYDYBRKA-XHZVRMJTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.3
• 重原子数：
  100
• 可旋转键数：
  31
• 环数：
  13.0
• sp3杂化的碳原子比例：
  0.51
• 拓扑面积：
  235
• 氢给体数：
  0
• 氢受体数：
  22

反应信息

• 作为反应物：
  描述：

  (1'S,2'S)-ethyl 2-O-[2-O-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)-6-O-benzoyl-3O,4O-(1',2'-dimethoxycyclohexan-1',2'-diyl)-α-D-mannopyranosyl]-6-O-benzoyl-3O,4O-(1',2'-dimethoxycyclohexan-1',2'-diyl)-1-thio-α-D-mannopyranoside 、 9-[(2R,3S,4S,5S,6R)-3,5-Bis-benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-4-hydroxy-tetrahydro-pyran-2-yloxy]-nonanoic acid methyl ester 在 2,6-二叔丁基吡啶 、 溴 、 silver trifluoromethanesulfonate 作用下， 生成 [(1S,3R,4R,6R,7S,8S,10S)-7-[[(1S,3R,4R,6R,7S,8S,10S)-4-(benzoyloxymethyl)-1,10-dimethoxy-7-[(2R,3S,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxy-2,5,9-trioxatricyclo[8.4.0.03,8]tetradecan-6-yl]oxy]-6-[(2R,3R,4S,5S,6R)-2-[[tert-butyl(diphenyl)silyl]oxymethyl]-6-(9-methoxy-9-oxononoxy)-3,5-bis(phenylmethoxy)oxan-4-yl]oxy-1,10-dimethoxy-2,5,9-trioxatricyclo[8.4.0.03,8]tetradecan-4-yl]methyl benzoate
  参考文献：
  名称：

  利用环己烷-1,2-二缩醛方法进行寡糖组装的新策略：高甘露糖型九糖的高效合成

  摘要：

  AbstractThe high‐mannose nonasaccharide 1 is part of the glycoprotein gp 120 of the viral coat of HIV‐1. The mannan portion of this triantennary glycan was prepared by a number of consecutive glycosidation steps without the need for any protecting‐group manipulation. This was achieved by carefully tuning the reactivity of the glycosyl donors by employing our cyclohexane‐1,2‐diacetal (CDA) methodology. The method was further extended with one‐pot procedures for oligosaccharide synthesis, thus reducing the number of steps to form the protected nonasaccharide 21 from the monosaccharide building blocks to five.

  DOI：

  10.1002/chem.19970030315
• 作为产物：
  描述：

  Phenyl 2,3,4,6-tetra-O-benzyl-1-seleno-α-D-mannopyranoside 在 N-碘代丁二酰亚胺 、 三氟甲磺酸 作用下， 以 乙醚 、 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 1.17h， 生成 (1'S,2'S)-ethyl 2-O-[2-O-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)-6-O-benzoyl-3O,4O-(1',2'-dimethoxycyclohexan-1',2'-diyl)-α-D-mannopyranosyl]-6-O-benzoyl-3O,4O-(1',2'-dimethoxycyclohexan-1',2'-diyl)-1-thio-α-D-mannopyranoside
  参考文献：
  名称：

  利用环己烷-1,2-二缩醛方法进行寡糖组装的新策略：高甘露糖型九糖的高效合成

  摘要：

  AbstractThe high‐mannose nonasaccharide 1 is part of the glycoprotein gp 120 of the viral coat of HIV‐1. The mannan portion of this triantennary glycan was prepared by a number of consecutive glycosidation steps without the need for any protecting‐group manipulation. This was achieved by carefully tuning the reactivity of the glycosyl donors by employing our cyclohexane‐1,2‐diacetal (CDA) methodology. The method was further extended with one‐pot procedures for oligosaccharide synthesis, thus reducing the number of steps to form the protected nonasaccharide 21 from the monosaccharide building blocks to five.

  DOI：

  10.1002/chem.19970030315

文献信息

• A New Strategy for Oligosaccharide Assembly Exploiting Cyclohexane-1,2-diacetal Methodology: An Efficient Synthesis of a High Mannose Type Nonasaccharide
  作者：Peter Grice、Steven V. Ley、Jörg Pietruszka、Helen M. I. Osborn、Henning W. M. Priepke、Stuart L. Warriner

  DOI：10.1002/chem.19970030315

  日期：——

  AbstractThe high‐mannose nonasaccharide 1 is part of the glycoprotein gp 120 of the viral coat of HIV‐1. The mannan portion of this triantennary glycan was prepared by a number of consecutive glycosidation steps without the need for any protecting‐group manipulation. This was achieved by carefully tuning the reactivity of the glycosyl donors by employing our cyclohexane‐1,2‐diacetal (CDA) methodology. The method was further extended with one‐pot procedures for oligosaccharide synthesis, thus reducing the number of steps to form the protected nonasaccharide 21 from the monosaccharide building blocks to five.