ethyl 6-O-benzyl-2,3-O-carbonate-1-thio-β-D-glucopyranoside | 392675-30-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 6-O-benzyl-2,3-O-carbonate-1-thio-β-D-glucopyranoside
• 英文别名: (3aR,4S,6R,7R,7aS)-4-ethylsulfanyl-7-hydroxy-6-(phenylmethoxymethyl)-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-2-one
• CAS: 392675-30-8
• 化学式: C₁₆H₂₀O₆S
• 分子量: 340.397
• InChiKey: LJXYJCSAEHLQNQ-QMIVOQANSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  99.5
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  ethyl 6-O-benzyl-2,3-O-carbonate-1-thio-β-D-glucopyranoside 在 4 A molecular sieve 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 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)-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 、 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-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.