3,4,6,7-tetra-O-TBDMS-6-D-glycero-D-heptosylglycal | 888487-39-6

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: 3,4,6,7-tetra-O-TBDMS-6-D-glycero-D-heptosylglycal
• CAS: 888487-39-6
• 化学式: C₃₁H₆₈O₅Si₄
• 分子量: 633.22
• InChiKey: RJZJWPJTIMICFJ-CWTOASCOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.09
• 重原子数：
  40.0
• 可旋转键数：
  10.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  46.15
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  3,4,6,7-tetra-O-TBDMS-6-D-glycero-D-heptosylglycal 在 15-冠醚-5 、 硝基甲烷 、 palladium on activated charcoal 、 四丁基氟化铵 、 氢气 作用下， 以 四氢呋喃 、 乙醇 、 乙酸乙酯 为溶剂， 反应 4.0h， 生成 2-deoxy-2-fluoro-6-D-grlycero-β-1-phosphoryl-D-heptoglucopyranoside disodium salt
  参考文献：
  名称：

  β-Selective One-Pot Fluorophosphorylation ofd,d-Heptosylglycals Mediated by Selectfluor

  摘要：

  AbstractThis study describes the development of a novel procedure of glycal fluorophosphorylation applied to the synthesis of a fluorinated analogue of an important bacterial metabolite. This procedure was applied to several heptose‐derived glycals, and the stereochemical outcome of the reaction was analyzed. Under optimized conditions, the reaction is β‐gluco selective, but a significant amount of the α‐gluco diastereomer is also generated.

  DOI：

  10.1002/ijch.201400148
• 作为产物：
  描述：

  3,4,6,7-tetra-O-acetyl-6-L-glycero-D-heptosylglycal 、 叔丁基二甲基氯硅烷 在 sodium 、 咪唑 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 以87%的产率得到3,4,6,7-tetra-O-TBDMS-6-D-glycero-D-heptosylglycal
  参考文献：
  名称：

  β-Selective One-Pot Fluorophosphorylation ofd,d-Heptosylglycals Mediated by Selectfluor

  摘要：

  AbstractThis study describes the development of a novel procedure of glycal fluorophosphorylation applied to the synthesis of a fluorinated analogue of an important bacterial metabolite. This procedure was applied to several heptose‐derived glycals, and the stereochemical outcome of the reaction was analyzed. Under optimized conditions, the reaction is β‐gluco selective, but a significant amount of the α‐gluco diastereomer is also generated.

  DOI：

  10.1002/ijch.201400148