ethyl 1-thio-2-O-β-D-xylopyranosyl-β-D-glucopyranoside | 946844-10-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 1-thio-2-O-β-D-xylopyranosyl-β-D-glucopyranoside
• CAS: 946844-10-6
• 化学式: C₁₃H₂₄O₉S
• 分子量: 356.394
• InChiKey: CNUJXNHPENOUFC-DXYZRIQWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.0
• 重原子数：
  23.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  149.07
• 氢给体数：
  6.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  ethyl 1-thio-2-O-β-D-xylopyranosyl-β-D-glucopyranoside 、 叔丁基二甲硅基三氟甲磺酸酯 在 2,6-二甲基吡啶 作用下， 反应 1.0h， 以100%的产率得到ethyl 3,4,6-tris-O-tert-butyldimethylsilyl-1-thio-2-O-(2,3,4-tris-O-tert-butyldimethylsilyl-β-D-xylopyranosyl)-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
• 作为产物：
  描述：

  2,3,4-三-O-乙酰基-1-O-(2,2,2-三氯亚氨代乙酰)-alpha-D-甘油-吡喃戊糖 在 4 A molecular sieve 、 三氟化硼乙醚 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 2.75h， 生成 ethyl 1-thio-2-O-β-D-xylopyranosyl-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