O-(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl) dichloro-cyanoacetimidate | 947335-86-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: O-(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl) dichloro-cyanoacetimidate
• 英文别名: [(2R,3S,4S,5R,6R)-3,4,5-triacetyloxy-6-(2,2-dichloro-2-cyanoethanimidoyl)oxyoxan-2-yl]methyl acetate
• CAS: 947335-86-6
• 化学式: C₁₇H₂₀Cl₂N₂O₁₀
• 分子量: 483.259
• InChiKey: DCAQHRDDVXDKPH-GZBLMMOJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  31
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  171
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  O-(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl) dichloro-cyanoacetimidate 、 甲基2,3,6-三-O-苄基-ALPHA-D-吡喃葡萄糖苷 在 三氟甲磺酸三甲基硅酯 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 以84%的产率得到Methyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1,4)-2,3,6-tri-O-benzyl-α-D-glucopyranoside
  参考文献：
  名称：

  Dichloro‐cyanoacetimidates as Glycosyl Donors

  摘要：

  Transformation of 1-O-unprotected glucose and galactose derivatives (1a-d) into O-glycosyl dichloro-cyanoacetimidates (2a-d) was performed with dichloro-cyanoacetonitrile in the presence of DBU as base. Reaction with different acceptors (3a-d) under TMSOTf catalysis afforded glycosides 4 in high yields. Competition experiments with O-glucopyranosyl trichloroacetimidate 10a, bearing a 4-tert-butylbenzyl group at 6-O, and O-glucopyranosyl dichloro-cyanoacetimidate 10b, bearing a 4-methylbenzyl group at 6-O, displayed similar reactivities for these two types of glycosyl donors.

  DOI：

  10.1080/07328300701410650
• 作为产物：
  描述：

  2,3,4,6-O-四乙酰基-D-半乳糖 、 二氯丙二腈 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以87%的产率得到O-(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl) dichloro-cyanoacetimidate
  参考文献：
  名称：

  Dichloro‐cyanoacetimidates as Glycosyl Donors

  摘要：

  Transformation of 1-O-unprotected glucose and galactose derivatives (1a-d) into O-glycosyl dichloro-cyanoacetimidates (2a-d) was performed with dichloro-cyanoacetonitrile in the presence of DBU as base. Reaction with different acceptors (3a-d) under TMSOTf catalysis afforded glycosides 4 in high yields. Competition experiments with O-glucopyranosyl trichloroacetimidate 10a, bearing a 4-tert-butylbenzyl group at 6-O, and O-glucopyranosyl dichloro-cyanoacetimidate 10b, bearing a 4-methylbenzyl group at 6-O, displayed similar reactivities for these two types of glycosyl donors.

  DOI：

  10.1080/07328300701410650