ethyl 2-O-(3,4,6-tri-O-benzyl-β-D-glucopyranosyl)-1-thio-β-D-glucopyranoside | 946844-13-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 2-O-(3,4,6-tri-O-benzyl-β-D-glucopyranosyl)-1-thio-β-D-glucopyranoside
• CAS: 946844-13-9
• 化学式: C₃₅H₄₄O₁₀S
• 分子量: 656.794
• InChiKey: AZLDZMMUUXJCLR-QZBKIKNBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.04
• 重原子数：
  46.0
• 可旋转键数：
  15.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.49
• 拓扑面积：
  136.3
• 氢给体数：
  4.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  ethyl 2-O-(3,4,6-tri-O-benzyl-β-D-glucopyranosyl)-1-thio-β-D-glucopyranoside 在 palladium hydroxide - carbon 氢气 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 7.0h， 生成
  参考文献：
  名称：

  Highly β-Selective and Direct Formation of 2-O-Glycosylated Glucosides by Ring Restriction into Twist-Boat

  摘要：

  Three disaccharide donors, ethyl 2- O- ( 2,3,4- tris- O- tert- butyldimethylsilyl-beta- (D)- xylopyranosyl)- 3,4,6- tris- O- tert- butyldimethylsilyl- 1- thio-beta- (D)- glucopyranoside, ethyl 2- O- ( 2,3,4- tris- O- tert- butyldimethylsilyl- alpha- (L)- rhamnopyranosyl)- 3,4,6- tris- O- tert- butyldimethylsilyl- 1- thio-beta- (D)- glucopyranoside, and ethyl 2- O( 2,3,4,6- tetrakis- O- tert- butyldimethylsilyl-beta- (D)- glucopyranosyl)- 3,4,6- tris- O- tert- butyldimethylsilyl- 1- thio-(beta)- (D)- glucopyranoside, produced a highly beta- selective glycosidation up to alpha/beta = 2/ 98 using MeOTf as the activator and 2,6- lutidine as an additive. The ring conformations of the glucose part in these disaccharide donors were all restricted to S-3(1), and the conformation would lead to the stereoselectivity.

  DOI：

  10.1021/ol070720b
• 作为产物：
  描述：

  2-O-benzoyl-3,4,6-tri-O-benzyl-D-glucopyranose 在 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 、 sodium methylate 、 caesium carbonate 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 18.0h， 生成 ethyl 2-O-(3,4,6-tri-O-benzyl-β-D-glucopyranosyl)-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  Highly β-Selective and Direct Formation of 2-O-Glycosylated Glucosides by Ring Restriction into Twist-Boat

  摘要：

  Three disaccharide donors, ethyl 2- O- ( 2,3,4- tris- O- tert- butyldimethylsilyl-beta- (D)- xylopyranosyl)- 3,4,6- tris- O- tert- butyldimethylsilyl- 1- thio-beta- (D)- glucopyranoside, ethyl 2- O- ( 2,3,4- tris- O- tert- butyldimethylsilyl- alpha- (L)- rhamnopyranosyl)- 3,4,6- tris- O- tert- butyldimethylsilyl- 1- thio-beta- (D)- glucopyranoside, and ethyl 2- O( 2,3,4,6- tetrakis- O- tert- butyldimethylsilyl-beta- (D)- glucopyranosyl)- 3,4,6- tris- O- tert- butyldimethylsilyl- 1- thio-(beta)- (D)- glucopyranoside, produced a highly beta- selective glycosidation up to alpha/beta = 2/ 98 using MeOTf as the activator and 2,6- lutidine as an additive. The ring conformations of the glucose part in these disaccharide donors were all restricted to S-3(1), and the conformation would lead to the stereoselectivity.

  DOI：

  10.1021/ol070720b