ethyl 2-O-(2,3,4-tris-O-tert-butyldimethylsilyl-α-L-rhamnopyranosyl)-3,4,6-tris-O-tert-butyldimethylsilyl-1-thio-β-D-glucopyranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 2-O-(2,3,4-tris-O-tert-butyldimethylsilyl-α-L-rhamnopyranosyl)-3,4,6-tris-O-tert-butyldimethylsilyl-1-thio-β-D-glucopyranoside
• 英文别名: TBDMS(-2)[TBDMS(-3)][TBDMS(-4)]Rha(a1-2)[TBDMS(-3)][TBDMS(-4)][TBDMS(-6)]Glc(b)-SEt；[(2S,3R,4R,5S,6S)-2-[(2S,3R,4R,5R,6R)-4,5-bis[[tert-butyl(dimethyl)silyl]oxy]-6-[[tert-butyl(dimethyl)silyl]oxymethyl]-2-ethylsulfanyloxan-3-yl]oxy-3,5-bis[[tert-butyl(dimethyl)silyl]oxy]-6-methyloxan-4-yl]oxy-tert-butyl-dimethylsilane
• 化学式: C₅₀H₁₁₀O₉SSi₆
• 分子量: 1056.0
• InChiKey: YJPHOMXVCOKLFC-KDWPDWDOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  15.57
• 重原子数：
  66
• 可旋转键数：
  23
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  108
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  ethyl 2-O-(2,3,4-tris-O-tert-butyldimethylsilyl-α-L-rhamnopyranosyl)-3,4,6-tris-O-tert-butyldimethylsilyl-1-thio-β-D-glucopyranoside 、 胆固醇 在 2,6-二甲基吡啶 、 4 A molecular sieve 、 三氟甲烷磺酸甲酯 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 cholesteryl 2-O-(2,3,4-tris-O-tert-butyldimethylsilyl-α-L-rhamnopyranosyl)-3,4,6-tris-O-tert-butyldimethylsilyl-β-D-glucopyranoside 、 cholesteryl 2-O-(2,3,4-tris-O-tert-butyldimethylsilyl-α-L-rhamnopyranosyl)-3,4,6-tris-O-tert-butyldimethylsilyl-α-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：

  、 叔丁基二甲硅基三氟甲磺酸酯 在 2,6-二甲基吡啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以42.2 mg的产率得到ethyl 2-O-(2,3,4-tris-O-tert-butyldimethylsilyl-α-L-rhamnopyranosyl)-3,4,6-tris-O-tert-butyldimethylsilyl-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