(2S)-2-[(3aS,4S,6R,6aS)-4-methoxy-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]-2-[acetyloxy(benzyl)amino]acetic acid | 1053709-95-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S)-2-[(3aS,4S,6R,6aS)-4-methoxy-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]-2-[acetyloxy(benzyl)amino]acetic acid
• CAS: 1053709-95-7
• 化学式: C₁₉H₂₅NO₈
• 分子量: 395.409
• InChiKey: YGDDBQAUYHOYCA-IWSXDTNSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  104
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  重氮甲烷 、 (2S)-2-[(3aS,4S,6R,6aS)-4-methoxy-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]-2-[acetyloxy(benzyl)amino]acetic acid 以 乙醚 为溶剂， 以64 mg的产率得到methyl 5-(N-benzylacetoxyamino)-5-deoxy-2,3-O-isopropyliden-1-O-methyl-α-L-gulo-hexafuranuronate
  参考文献：
  名称：

  A General Method for the Vinylation of Nitrones. Synthesis of Allyl Hydroxylamines and Allyl Amines

  摘要：

  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.

  DOI：

  10.1080/00397910008087449
• 作为产物：
  描述：

  5-(acetoxyamino)-N-benzyl-5-deoxy-5-vinyl-2,3-O-isopropylidene-1-O-methyl-α-D-manno-1,4-pentofuranoside 在 ruthenium trichloride 、 sodium periodate 作用下， 以 四氯化碳 、 水 、 乙腈 为溶剂， 反应 0.5h， 生成 (2S)-2-[(3aS,4S,6R,6aS)-4-methoxy-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]-2-[acetyloxy(benzyl)amino]acetic acid
  参考文献：
  名称：

  A General Method for the Vinylation of Nitrones. Synthesis of Allyl Hydroxylamines and Allyl Amines

  摘要：

  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.

  DOI：

  10.1080/00397910008087449

文献信息

• Stereoselective Addition of 2-Furyllithium and 2-Thiazolyllithium to Sugar Nitrones. Synthesis of Carbon-Linked Glycoglycines
  作者：Alessandro Dondoni、Federico Junquera、Francisco Luis Merchán、Pedro Merino、Marie-Christine Scherrmann、Tomas Tejero

  DOI：10.1021/jo970290a

  日期：1997.8.1

  A route to epimeric carbon-linked glycoglycines that exploits the stereoselective addition of 2-lithiofuran and 2-lithiothiazole to sugar nitrones has been described. The reaction occurs with opposite diastereofacial selectivity depending on whether the free nitrone or the diethyl aluminum chloride precomplexed derivative is employed. The resulting furyl or thiazolyl hydroxylamines are dehydroxylated to amines by the action of titanium(III) chloride. From these compounds the amino acids are revealed by the oxidative cleavage of the furan ring or by the conversion of the thiazole into the formyl group and oxidation to carboxylic acid. Compounds have been prepared wherein the alpha-amino acid moiety is installed at C-4 and C-1 of furanoses (ribo, manno, xylo, and lyxo) and at C-5 and C-1 of a pyranose (galacto).