Carbonic acid (2R,3R,4S,5R,6S)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yl ester 2,5-dioxo-pyrrolidin-1-yl ester | 228873-48-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Carbonic acid (2R,3R,4S,5R,6S)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yl ester 2,5-dioxo-pyrrolidin-1-yl ester
• 英文别名: (2,5-dioxopyrrolidin-1-yl) [(2R,3R,4S,5R,6S)-6-methoxy-4,5-bis(phenylmethoxy)-2-(phenylmethoxymethyl)oxan-3-yl] carbonate
• CAS: 228873-48-1
• 化学式: C₃₃H₃₅NO₁₀
• 分子量: 605.642
• InChiKey: VYXZVDAZXNDNAQ-RITJHEIASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  44
• 可旋转键数：
  15
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  119
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  2,3,4,6-tetra-O-benzoyl-D-glucopyranose 、 Carbonic acid (2R,3R,4S,5R,6S)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yl ester 2,5-dioxo-pyrrolidin-1-yl ester 在 potassium carbonate 作用下， 以 甲苯 为溶剂， 反应 240.0h， 以79%的产率得到[(2R,3R,4S,5R,6S)-3,4,5-tribenzoyloxy-6-[(2R,3R,4S,5R,6S)-6-methoxy-4,5-bis(phenylmethoxy)-2-(phenylmethoxymethyl)oxan-3-yl]oxycarbonyloxyoxan-2-yl]methyl benzoate
  参考文献：
  名称：

  An efficient synthesis of mixed β-carbonates of acyl-protected sugar and their decarboxylative glycosidation promoted by trimethylsilyl trifluoromethanesulfonate

  摘要：

  Mixed beta-carbonates of acyl-protected sugar are stereoselectively prepared by using an N-succinimidyl group for activation of the acceptor alcohol carbonate. The glycosyl carbonates are smoothly decarboxylated by trimethylsilyl trifluoromethanesulfonate (Me3SiOTf) to give beta-glycosides preferentially in high yields. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00843-6
• 作为产物：
  描述：

  甲基2,3,6-三-O-苄基-ALPHA-D-吡喃葡萄糖苷 、 N,N'-二琥珀酰亚胺基碳酸酯 在 三乙胺 作用下， 以 乙腈 为溶剂， 生成 Carbonic acid (2R,3R,4S,5R,6S)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yl ester 2,5-dioxo-pyrrolidin-1-yl ester
  参考文献：
  名称：

  An efficient synthesis of mixed β-carbonates of acyl-protected sugar and their decarboxylative glycosidation promoted by trimethylsilyl trifluoromethanesulfonate

  摘要：

  Mixed beta-carbonates of acyl-protected sugar are stereoselectively prepared by using an N-succinimidyl group for activation of the acceptor alcohol carbonate. The glycosyl carbonates are smoothly decarboxylated by trimethylsilyl trifluoromethanesulfonate (Me3SiOTf) to give beta-glycosides preferentially in high yields. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00843-6