5-[N-benzyl-N-[(1,1-dimethylethoxy)carbonyl]amino]-6,7-O-isopropylidene-2,3,5-trideoxy-D-ribo-hept-2-enono-1,4-lactone | 858662-07-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-[N-benzyl-N-[(1,1-dimethylethoxy)carbonyl]amino]-6,7-O-isopropylidene-2,3,5-trideoxy-D-ribo-hept-2-enono-1,4-lactone
• 英文别名: tert-butyl N-benzyl-N-[(S)-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-[(2S)-5-oxo-2H-furan-2-yl]methyl]carbamate
• CAS: 858662-07-4
• 化学式: C₂₂H₂₉NO₆
• 分子量: 403.475
• InChiKey: JTFYFPZOSIJRSY-SCTDSRPQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  74.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-[N-benzyl-N-[(1,1-dimethylethoxy)carbonyl]amino]-6,7-O-isopropylidene-2,3,5-trideoxy-D-ribo-hept-2-enono-1,4-lactone 在 吡啶 、 二环己烷并-18-冠醚-6 、 potassium permanganate 、 二异丁基氢化铝 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 28.5h， 生成 5-[N-benzyl-N-[(1,1-dimethylethoxy)carbonyl]amino]-6,7-O-isopropylidene-5-deoxy-D-glycero-D-alloheptofuranose 1,2,3-triacetate
  参考文献：
  名称：

  A formal synthesis of thymine polyoxin C

  摘要：

  A convergent stereoselective synthesis of thymine polyoxin C 1 has been conducted utilizing the benzylimine of D-glueraldehyde acetonide 7 as a chiral controller and 2-trimethylsilyloxy furan 8 as a four-carbon synthon. In the presence of catalytic BF(3)center dot OEt2, 8 has been found to add to 7 with a moderately high level of stereoselectivity. Intermediate 4-(aminoalkyl)-2-butenolide 6 proved to be an ideal candidate for elaboration to 3. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.03.034
• 作为产物：
  描述：

  (2S)-2,3-O-isopropylideneglyceraldehyde N-benzylimine 在 三氟化硼乙醚 作用下， 以 二氯甲烷 、 叔丁醇 为溶剂， 反应 9.0h， 生成 5-[N-benzyl-N-[(1,1-dimethylethoxy)carbonyl]amino]-6,7-O-isopropylidene-2,3,5-trideoxy-D-ribo-hept-2-enono-1,4-lactone
  参考文献：
  名称：

  A formal synthesis of thymine polyoxin C

  摘要：

  A convergent stereoselective synthesis of thymine polyoxin C 1 has been conducted utilizing the benzylimine of D-glueraldehyde acetonide 7 as a chiral controller and 2-trimethylsilyloxy furan 8 as a four-carbon synthon. In the presence of catalytic BF(3)center dot OEt2, 8 has been found to add to 7 with a moderately high level of stereoselectivity. Intermediate 4-(aminoalkyl)-2-butenolide 6 proved to be an ideal candidate for elaboration to 3. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.03.034

文献信息

• A formal synthesis of thymine polyoxin C
  作者：Kenn E. Harding、Jack M. Southard

  DOI：10.1016/j.tetasy.2005.03.034

  日期：2005.5

  A convergent stereoselective synthesis of thymine polyoxin C 1 has been conducted utilizing the benzylimine of D-glueraldehyde acetonide 7 as a chiral controller and 2-trimethylsilyloxy furan 8 as a four-carbon synthon. In the presence of catalytic BF(3)center dot OEt2, 8 has been found to add to 7 with a moderately high level of stereoselectivity. Intermediate 4-(aminoalkyl)-2-butenolide 6 proved to be an ideal candidate for elaboration to 3. (C) 2005 Elsevier Ltd. All rights reserved.