6'-(1',2':3'',4'-diisopropylidenegalactopyranosyl) 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-(phenylthio)-β-D-glucopyranoside | 139378-93-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6'-(1',2':3'',4'-diisopropylidenegalactopyranosyl) 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-(phenylthio)-β-D-glucopyranoside
• 英文别名: (1S,2R,6R,8R,9S)-8-[[(4aR,6R,7R,8S,8aR)-2-phenyl-8-phenylmethoxy-7-phenylsulfanyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-6-yl]oxymethyl]-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.02,6]dodecane
• CAS: 139378-93-1；139378-94-2
• 化学式: C₃₈H₄₄O₁₀S
• 分子量: 692.827
• InChiKey: OZMZLLPBNAMEBP-GKBABDPGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.98
• 重原子数：
  49.0
• 可旋转键数：
  9.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  92.3
• 氢给体数：
  0.0
• 氢受体数：
  11.0

反应信息

• 作为产物：
  描述：

  1,5-anhydro-3-O-benzyl-4,6-O-benzylidene-2-deoxy-D-arabino-hex-1-enitol 、 phenyl(bisphenylthio)sulfonium hexachloroantimonate 、 双丙酮半乳糖 在 molecular sieve 、 三丁基氧化锡 作用下， 生成 6'-(1',2':3'',4'-diisopropylidenegalactopyranosyl) 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-(phenylthio)-β-D-glucopyranoside 、 6'-(1',2':3',4'-diisopropylidenegalactopyranosyl) 3-O-benzyl-2-deoxy-2-(phenylthio)-β-D-glucopyranoside 、 6'-(1',2':3',4'-diisopropylidenegalactopyranosyl) 3-O-benzyl-2-deoxy-2-(phenylthio)-α-D-mannopyranoside
  参考文献：
  名称：

  Arylbis(arylthio)sulfonium salts as reagents for the synthesis of 2-deoxy-.beta.-glycosides

  摘要：

  The title sulfonium salts undergo electrophilic addition to glycals in the presence of alcohols to form principally beta-glycosides. A substituent effect study has shown that the reagent with a p-tolylthio group is the most face-selective. By variation of the alcohol nucleophile, it has been shown that face selectivity is also dependent on the structure of the nucleophile. One instance of double diastereodifferentiation was uncovered when the racemic alcohol 23.5 was used in a reaction with tribenzyl glucal 22.1. The effect of glycal substitution on the face selectivity has led to the postulation of a heretofore unrecognized and still unexplained stereoelectronic effect.

  DOI：

  10.1021/jo00033a033