5-(N-benzylamino)-6,7-O-isopropylidene-2,3,5-trideoxy-D-ribo-hept-2-enonic acid 1,4-lactone | 140193-76-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-(N-benzylamino)-6,7-O-isopropylidene-2,3,5-trideoxy-D-ribo-hept-2-enonic acid 1,4-lactone
• 英文别名: 5-(N-benzylamino)-6,7-O-isopropylidene-2,3,5-trideoxy-D-ribo-hept-2-enono-1,4-lactone；(2S)-2-[(S)-(benzylamino)-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl]-2H-furan-5-one
• CAS: 140193-76-6
• 化学式: C₁₇H₂₁NO₄
• 分子量: 303.358
• InChiKey: WSCVZBRSALZIMQ-LZWOXQAQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  56.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-(N-benzylamino)-6,7-O-isopropylidene-2,3,5-trideoxy-D-ribo-hept-2-enonic acid 1,4-lactone 在 nickel dichloride 2,6-二甲基吡啶 、 sodium tetrahydroborate 、 溶剂黄146 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 25.67h， 生成 (1'S,5S,6S)-1-benzyl-5-(tert-butyldimethylsilanyloxy)-6-(1,2-dihydroxyethyl)piperidin-2-one
  参考文献：
  名称：

  Variable Strategy toward Carbasugars and Relatives. 6.¹ Diastereoselective Synthesis of 2-Deoxy-2-amino-5a-carba-β-l-mannopyranuronic Acid and 2-Deoxy-2-amino-5a-carba-β-l-mannopyranose

  摘要：

  Efficient, total syntheses of novel 2-deoxy-2-amino-5a-carba-beta-L-mannopyranuronic acid (1) and 2-deoxy-2-amino-5a-carba-beta-L-mannopyranose (2), a positional stereoisomer of validamine, have been achieved in 28% and 24% overall yields and in 12 steps and 13 steps, respectively, from 2-[(tert-butyldimethylsilyl)oxy]furan (3) and (2S)-2,3-O-isopropylideneglyceraldehyde N-benzyl imine (4) via two highly diastereoselective Mukaiyama aldol-related chemical maneuvers. The strategy, which furnishes the targeted carbasugars in enantiopure forms, allows for complete control of the configuration at all five contiguous stereocenters of the targets by utilizing the sole element of chirality present in the aldimine progenitor 4.

  DOI：

  10.1021/jo0357216
• 作为产物：
  描述：

  (R)-(+)-2,2-二甲基-1,3-二氧戊环-4-甲醛 在 叔丁基二甲硅基三氟甲磺酸酯 、 magnesium sulfate 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 5-(N-benzylamino)-6,7-O-isopropylidene-2,3,5-trideoxy-D-ribo-hept-2-enonic acid 1,4-lactone
  参考文献：
  名称：

  Variable Strategy toward Carbasugars and Relatives. 6.¹ Diastereoselective Synthesis of 2-Deoxy-2-amino-5a-carba-β-l-mannopyranuronic Acid and 2-Deoxy-2-amino-5a-carba-β-l-mannopyranose

  摘要：

  Efficient, total syntheses of novel 2-deoxy-2-amino-5a-carba-beta-L-mannopyranuronic acid (1) and 2-deoxy-2-amino-5a-carba-beta-L-mannopyranose (2), a positional stereoisomer of validamine, have been achieved in 28% and 24% overall yields and in 12 steps and 13 steps, respectively, from 2-[(tert-butyldimethylsilyl)oxy]furan (3) and (2S)-2,3-O-isopropylideneglyceraldehyde N-benzyl imine (4) via two highly diastereoselective Mukaiyama aldol-related chemical maneuvers. The strategy, which furnishes the targeted carbasugars in enantiopure forms, allows for complete control of the configuration at all five contiguous stereocenters of the targets by utilizing the sole element of chirality present in the aldimine progenitor 4.

  DOI：

  10.1021/jo0357216

文献信息

• Total synthesis of both enentiomers of trans-β-hydroxyppecolic acid
  作者：Lucia Battistini、Franca Zanardi、Gloria Rassu、Pietro Spanu、Giorgio Pelosi、Giovanna Gasparri Fava、Marisa Belicchi Ferrari、Giovanni Casiraghi

  DOI：10.1016/s0957-4166(97)00344-3

  日期：1997.9

  trans-beta-Hydroxypipecolic acids of both L-and D-series, L-1 and D-1, have been straightforwardly prepared in 14% and 15% yields, respectively starting from glyceraldehyde imines D-7 and L-7 as useful three-carbon chirons. The key feature of these parallel syntheses lies on the highly diastereoselective character of the initial coupling manoeuver between silyloxy furan TBSOF and imines 7, which ultimately accounts for the relative, and hence absolute configuration of the target pipecolic acids. (C) 1997 Elsevier Science Ltd.
• Diastereoselective synthesis of a novel lactam peptidomimetic exploiting vinylogous Mannich addition of 2-silyloxyfuran reagents
  作者：Lucia Battistini、Gloria Rassu、Luigi Pinna、Franca Zanardi、Giovanni Casiraghi

  DOI：10.1016/s0957-4166(99)00051-8

  日期：1999.2

  The total synthesis of a potential inhibitor of HIV-protease-the chiral nonracemic six-membered hydroxy lactam 6-has been accomplished, that involves, as key reaction, the highly diastereoselective vinylogous Mannich addition of furan-based silyloxy diene 7 to glyceraldeyde imine 8. (C) 1999 Elsevier Science Ltd. All rights reserved.
• 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.
• Variable Strategy toward Carbasugars and Relatives. 6.¹ Diastereoselective Synthesis of 2-Deoxy-2-amino-5a-carba-β-<scp>l</scp>-mannopyranuronic Acid and 2-Deoxy-2-amino-5a-carba-β-<scp>l</scp>-mannopyranose
  作者：Gloria Rassu、Luciana Auzzas、Vincenzo Zambrano、Paola Burreddu、Luigi Pinna、Lucia Battistini、Franca Zanardi、Giovanni Casiraghi

  DOI：10.1021/jo0357216

  日期：2004.3.1

  Efficient, total syntheses of novel 2-deoxy-2-amino-5a-carba-beta-L-mannopyranuronic acid (1) and 2-deoxy-2-amino-5a-carba-beta-L-mannopyranose (2), a positional stereoisomer of validamine, have been achieved in 28% and 24% overall yields and in 12 steps and 13 steps, respectively, from 2-[(tert-butyldimethylsilyl)oxy]furan (3) and (2S)-2,3-O-isopropylideneglyceraldehyde N-benzyl imine (4) via two highly diastereoselective Mukaiyama aldol-related chemical maneuvers. The strategy, which furnishes the targeted carbasugars in enantiopure forms, allows for complete control of the configuration at all five contiguous stereocenters of the targets by utilizing the sole element of chirality present in the aldimine progenitor 4.