4-O-(3,4-O-isopropylidene-6-O-trityl-β-D-lyxo-hexopyranosyl-2-ulose)-2,3:5,6-di-O-isopropylidene-aldehydo-D-glucose dimethyl acetal | 263845-18-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 4-O-(3,4-O-isopropylidene-6-O-trityl-β-D-lyxo-hexopyranosyl-2-ulose)-2,3:5,6-di-O-isopropylidene-aldehydo-D-glucose dimethyl acetal
• 英文别名: (3aS,4R,6S,7aS)-6-[(R)-[(4S,5R)-5-(dimethoxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methoxy]-2,2-dimethyl-4-(trityloxymethyl)-4,7a-dihydro-3aH-[1,3]dioxolo[4,5-c]pyran-7-one
• CAS: 263845-18-7
• 化学式: C₄₂H₅₂O₁₂
• 分子量: 748.868
• InChiKey: PRBHQZBKIHXWJL-RNMKABDQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  54
• 可旋转键数：
  13
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  119
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  4-O-(3,4-O-isopropylidene-6-O-trityl-β-D-lyxo-hexopyranosyl-2-ulose)-2,3:5,6-di-O-isopropylidene-aldehydo-D-glucose dimethyl acetal 在 盐酸羟胺 作用下， 以 吡啶 为溶剂， 生成 (E)-4-O-(2-deoxy-3,4-O-isopropylidene-2-hydroxyimino-6-O-trityl-β-D-lyxo-hexopyranosyl)-2,3:5,6-di-O-isopropylidene-aldehydo-D-glucose dimethyl acetal 、 (Z)-4-O-(2-deoxy-3,4-O-isopropylidene-2-hydroxyimino-6-O-trityl-β-D-lyxo-hexopyranosyl)-2,3:5,6-di-O-isopropylidene-aldehydo-D-glucose dimethyl acetal
  参考文献：
  名称：

  Stereoselective Synthesis of 4-O-(2-Acetamido-2-Deoxy-β-D-Talopyranosyl)-D-Glucose Derivatives from Lactose

  摘要：

  The 6-O-trityl derivative of 2,3:5,6:3',4'-O-isopropylidenelactose dimethyl acetal (1) was converted through an oxidation/oximation/reduction sequence involving the free 2-OH group of the D-galactose moiety into the protected disaccharide 5 in up to 75% yield. The complete deprotection of 5 produced the disaccharide 4-O-(2-acetamido-2-deoxy-beta-D-talopyranosy)-D-glucose glucose (7a). The oxime LiAlH4 reduction step produced some unexpected side-products, the most abundant of which, the dimethyl acetal 9, deriving from cleavage of the D-glucose moiety, was formed only when the reaction was conducted in refluxing THF, but not when Et2O was used as the solvent.

  DOI：

  10.1080/07328300008544066
• 作为产物：
  描述：

  4-O-(6-O-trityl-3,4-O-isopropylidene-β-D-galactopyranosyl)-2,3:5,6-di-O-isopropylidene-D-glucose dimethyl acetal 在 N-甲基吲哚酮 、 四丙基高钌酸铵 、 4 A molecular sieve 作用下， 以 二氯甲烷 为溶剂， 反应 3.5h， 以98%的产率得到4-O-(3,4-O-isopropylidene-6-O-trityl-β-D-lyxo-hexopyranosyl-2-ulose)-2,3:5,6-di-O-isopropylidene-aldehydo-D-glucose dimethyl acetal
  参考文献：
  名称：

  Stereoselective Synthesis of 4-O-(2-Acetamido-2-Deoxy-β-D-Talopyranosyl)-D-Glucose Derivatives from Lactose

  摘要：

  The 6-O-trityl derivative of 2,3:5,6:3',4'-O-isopropylidenelactose dimethyl acetal (1) was converted through an oxidation/oximation/reduction sequence involving the free 2-OH group of the D-galactose moiety into the protected disaccharide 5 in up to 75% yield. The complete deprotection of 5 produced the disaccharide 4-O-(2-acetamido-2-deoxy-beta-D-talopyranosy)-D-glucose glucose (7a). The oxime LiAlH4 reduction step produced some unexpected side-products, the most abundant of which, the dimethyl acetal 9, deriving from cleavage of the D-glucose moiety, was formed only when the reaction was conducted in refluxing THF, but not when Et2O was used as the solvent.

  DOI：

  10.1080/07328300008544066

文献信息

• Stereoselective Synthesis of 4-<i>O</i>-(2-Acetamido-2-Deoxy-β-D-Talopyranosyl)-D-Glucose Derivatives from Lactose
  作者：Pier Luigi Barili、Giancarlo Berti、Giorgio Catelani、Felicia D'Andrea、Leonardo Puccioni

  DOI：10.1080/07328300008544066

  日期：2000.1

  The 6-O-trityl derivative of 2,3:5,6:3',4'-O-isopropylidenelactose dimethyl acetal (1) was converted through an oxidation/oximation/reduction sequence involving the free 2-OH group of the D-galactose moiety into the protected disaccharide 5 in up to 75% yield. The complete deprotection of 5 produced the disaccharide 4-O-(2-acetamido-2-deoxy-beta-D-talopyranosy)-D-glucose glucose (7a). The oxime LiAlH4 reduction step produced some unexpected side-products, the most abundant of which, the dimethyl acetal 9, deriving from cleavage of the D-glucose moiety, was formed only when the reaction was conducted in refluxing THF, but not when Et2O was used as the solvent.