2'(RS)-(1'-oxo-1',2',3',4'-tetrahydronaphthyl) 3,4,6-tri-O-benzyl-2-deoxy-2-(phenylthio)-β-D-glucopyranoside | 124718-65-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2'(RS)-(1'-oxo-1',2',3',4'-tetrahydronaphthyl) 3,4,6-tri-O-benzyl-2-deoxy-2-(phenylthio)-β-D-glucopyranoside
• 英文别名: 2-[(2S,3R,4S,5R,6R)-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)-3-phenylsulfanyloxan-2-yl]oxy-3,4-dihydro-2H-naphthalen-1-one
• CAS: 124718-65-6
• 化学式: C₄₃H₄₂O₆S
• 分子量: 686.869
• InChiKey: KZAKEBKZBGAEHS-SRHNPMDQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.3
• 重原子数：
  50
• 可旋转键数：
  14
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  88.5
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  3,4,6-三苄氧基-D-葡萄烯糖 、 2-hydroxy-1-tetralone 、 alkaline earth salt of/the/ methylsulfuric acid 以 二氯甲烷 为溶剂， 以45%的产率得到2'(RS)-(1'-oxo-1',2',3',4'-tetrahydronaphthyl) 3,4,6-tri-O-benzyl-2-deoxy-2-(phenylthio)-β-D-glucopyranoside
  参考文献：
  名称：

  Aureolic acid antibiotics: a simple method for 2-deoxy-.beta.-glycosidation

  摘要：

  DOI：

  10.1021/jo00288a003

文献信息

• Arylbis(arylthio)sulfonium salts as reagents for the synthesis of 2-deoxy-.beta.-glycosides
  作者：Gurmit Grewal、Neelu Kaila、Richard W. Franck

  DOI：10.1021/jo00033a033

  日期：1992.3

  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.
• RAMESH, SUBBAN;KAILA, NEELU;GREWAL, GURMIT;FRANCK, RICHARD W., J. ORG. CHEM., 55,(1990) N, C. 5-7
  作者：RAMESH, SUBBAN、KAILA, NEELU、GREWAL, GURMIT、FRANCK, RICHARD W.

  DOI：——

  日期：——