methyl (2R,3S)-2-(N-benzylacetoxyamino)-3,4-dihydroxy-3,4-O-isopropylidenebutanoate | 198418-09-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (2R,3S)-2-(N-benzylacetoxyamino)-3,4-dihydroxy-3,4-O-isopropylidenebutanoate
• 英文别名: methyl (2R)-2-[acetyloxy(benzyl)amino]-2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]acetate
• CAS: 198418-09-6
• 化学式: C₁₇H₂₃NO₆
• 分子量: 337.373
• InChiKey: NABJMPSONMSZLM-HUUCEWRRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  74.3
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  二碳酸二叔丁酯 、 methyl (2R,3S)-2-(N-benzylacetoxyamino)-3,4-dihydroxy-3,4-O-isopropylidenebutanoate 在 palladium dihydroxide 氢气 作用下， 以 甲醇 为溶剂， 反应 144.0h， 以83%的产率得到methyl (2R)-2-[(tert-butylcarbonyl)amino]-2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]ethanoate
  参考文献：
  名称：

  Diastereoselective nucleophilic addition of acetylide to N-benzyl-2, nitrone (BIGN). Stereodivergent synthesis of β-hydroxy-α-(hydroxyamino)- and β-hydroxy-α-amino acids

  摘要：

  The stereocontrolled nucleophilic addition of lithium trimethylsilyl acetylide to the N-benzyl nitrone (BIGN) derived from 2,3-O-isopropylidene-D-glyceraldehyde, followed by oxidative cleavage of the ensuing propargyl hydroxylamines resulted in an efficient stereodivergent synthesis of fully protected epimeric N-hydroxy alpha-amino esters 8 and 13 as well as the corresponding cw-amino esters 9 and 14. (C) 1997 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00438-2
• 作为产物：
  描述：

  (R)-(+)-2,2-二甲基-1,3-二氧戊环-4-甲醛 在 吡啶 、 ruthenium trichloride 、 sodium periodate 、 四丁基氟化铵 、 氯化二乙基铝 、 magnesium sulfate 作用下， 以 四氢呋喃 、 四氯化碳 、 乙醚 、 二氯甲烷 、 乙腈 为溶剂， 反应 6.44h， 生成 methyl (2R,3S)-2-(N-benzylacetoxyamino)-3,4-dihydroxy-3,4-O-isopropylidenebutanoate
  参考文献：
  名称：

  Diastereoselective nucleophilic addition of acetylide to N-benzyl-2, nitrone (BIGN). Stereodivergent synthesis of β-hydroxy-α-(hydroxyamino)- and β-hydroxy-α-amino acids

  摘要：

  The stereocontrolled nucleophilic addition of lithium trimethylsilyl acetylide to the N-benzyl nitrone (BIGN) derived from 2,3-O-isopropylidene-D-glyceraldehyde, followed by oxidative cleavage of the ensuing propargyl hydroxylamines resulted in an efficient stereodivergent synthesis of fully protected epimeric N-hydroxy alpha-amino esters 8 and 13 as well as the corresponding cw-amino esters 9 and 14. (C) 1997 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00438-2

文献信息

• A General Method for the Vinylation of Nitrones. Synthesis of Allyl Hydroxylamines and Allyl Amines
  作者：Pedro Merino、Sonia Anoro、Santiago Franco、Jose M. Gascon、Victor Martin、Francisco L. Merchan、Julia Revuelta、Tomas Tejero、Victoria Tuñon

  DOI：10.1080/00397910008087449

  日期：2000.8

  An examination of the vinylation of several nitrones is presented. Whereas a complete diastereofacial discrimination was observed upon the addition of vinyl organometallic reagents to alpha-alkoxy nitrones, the same reaction with alpha-amino nitrones pave syn adducts in all cases, with the only exception of a L-serine-derived alpha-amino monoprotected nitrone. The obtained allyl hydroxylamines were easily transformed into synthetically valuable allyl amines.