ethyl 6-O-benzyl-2,3-O-carbonate-4-O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-1-thio-β-D-glucopyranoside | 392675-39-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: ethyl 6-O-benzyl-2,3-O-carbonate-4-O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-1-thio-β-D-glucopyranoside
• 英文别名: [(2R,3S,4S,5R,6S)-6-[[(3aR,4S,6R,7R,7aS)-4-ethylsulfanyl-2-oxo-6-(phenylmethoxymethyl)-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-7-yl]oxy]-3,4,5-tribenzoyloxyoxan-2-yl]methyl benzoate
• CAS: 392675-39-7
• 化学式: C₅₀H₄₆O₁₅S
• 分子量: 918.972
• InChiKey: KQIIFLIOWGIBGR-KXAQXYCQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.8
• 重原子数：
  66
• 可旋转键数：
  21
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  203
• 氢给体数：
  0
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  双丙酮半乳糖 、 ethyl 6-O-benzyl-2,3-O-carbonate-4-O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-1-thio-β-D-glucopyranoside 在 4 A molecular sieve 、 2,6-二叔丁基-4-甲基吡啶 、 silver trifluoromethanesulfonate 、 苯次磺酰氯 作用下， 以 1,4-二氧六环 、 甲苯 为溶剂， 反应 18.5h， 生成 1,2:3,4-di-O-isopropylidene-6-O-(6-O-benzyl-2,3-O-carbonate-4-O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-β-D-glucopyranosyl)-α-D-galactopyranose 、 1,2:3,4-di-O-isopropylidene-6-O-(6-O-benzyl-2,3-O-carbonate-4-O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-α-D-glucopyranosyl)-α-D-galactopyranose
  参考文献：
  名称：

  Thioglycosides Protected as Trans-2,3-Cyclic Carbonates in Chemoselective Glycosylations

  摘要：

  [GRAPHICS]Thioglycosides protected as trans-2,3-cyclic carbonates have significantly lower anomeric reactivities than fully acylated and N-acyl-protected thioglycosides and can be used as acceptors in chemoselective glycosylations with a wide range of thioglycosyl donors. The resulting thioglycosides can be further activated to give 1,2-cis-linked glycosides.

  DOI：

  10.1021/ol016869j
• 作为产物：
  描述：

  ethyl 4,6-O-benzylidene-1-thio-β-D-glucopyranoside 在 盐酸 、 3 A molecular sieve 、 4 A molecular sieve 、 sodium cyanoborohydride 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 甲苯 为溶剂， 反应 0.58h， 生成 ethyl 6-O-benzyl-2,3-O-carbonate-4-O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  Thioglycosides Protected as Trans-2,3-Cyclic Carbonates in Chemoselective Glycosylations

  摘要：

  [GRAPHICS]Thioglycosides protected as trans-2,3-cyclic carbonates have significantly lower anomeric reactivities than fully acylated and N-acyl-protected thioglycosides and can be used as acceptors in chemoselective glycosylations with a wide range of thioglycosyl donors. The resulting thioglycosides can be further activated to give 1,2-cis-linked glycosides.

  DOI：

  10.1021/ol016869j

文献信息

• Thioglycosides Protected as Trans-2,3-Cyclic Carbonates in Chemoselective Glycosylations
  作者：Tong Zhu、Geert-Jan Boons

  DOI：10.1021/ol016869j

  日期：2001.12.1

  [GRAPHICS]Thioglycosides protected as trans-2,3-cyclic carbonates have significantly lower anomeric reactivities than fully acylated and N-acyl-protected thioglycosides and can be used as acceptors in chemoselective glycosylations with a wide range of thioglycosyl donors. The resulting thioglycosides can be further activated to give 1,2-cis-linked glycosides.