(S)-Dibenzylamino-[(3aR,5R,6R,6aR)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-6-hydroxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl]-acetic acid | 189456-77-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (S)-Dibenzylamino-[(3aR,5R,6R,6aR)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-6-hydroxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl]-acetic acid
• 英文别名: (2S)-2-[(3aR,5R,6R,6aR)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-6-hydroxy-2,2-dimethyl-5,6a-dihydro-3aH-furo[2,3-d][1,3]dioxol-6-yl]-2-(dibenzylamino)acetic acid
• CAS: 189456-77-7
• 化学式: C₂₈H₃₅NO₈
• 分子量: 513.588
• InChiKey: IQYPNDQITJMREL-QUCBLMSRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  37
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  107
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (S)-Dibenzylamino-[(3aR,5R,6R,6aR)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-6-hydroxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl]-acetic acid 在 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 (2S),(3'R)-3'-N-dibenzyl-1,2:5,6-di-O-isopropylidene-α-D-allofuranos-3-spiropropiolactone
  参考文献：
  名称：

  (3R,2'S)-2'-N-Dibenzylamino-1,2:5,6-di-O-isopropylidène-α-D-allofuranose-3-spiro-3'-β-propiolactone

  摘要：

  The stereochemistry of (3R,2'S)-2'-N-dibenzylamino-1,2:5,6-di-O-isopropylidene-alpha-D-allofuranose-3-spiro-3'-propano-3-lactone, C28H33NO7, has been established, The three five-membered rings adopt envelope conformations, The spiropropiolactone ring is practically planar.

  DOI：

  10.1107/s0108270196014461
• 作为产物：
  描述：

  1,2:5,6-二-o-异亚丙基-alpha-d-ribo-3-己呋喃核糖 在 sodium hydroxide 、 lithium diisopropyl amide 作用下， 以 1,4-二氧六环 为溶剂， 反应 25.33h， 生成 (S)-Dibenzylamino-[(3aR,5R,6R,6aR)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-6-hydroxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl]-acetic acid
  参考文献：
  名称：

  Diastereoselective synthesis of glycosyl-α-aminoacids

  摘要：

  Asymmetric synthesis of various glycosyl-alpha-aminoacids is described. The approach involves the diastereoselective condensation of glycine enolates on the carbonyl in position 3 of the suitably protected alpha-D-ribohexafuranos-3-ulose. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00067-0

文献信息

• (3<i>R</i>,2'<i>S</i>)-2'-<i>N</i>-Dibenzylamino-1,2:5,6-di-<i>O</i>-isopropylidène-α-<scp>D</scp>-allofuranose-3-spiro-3'-β-propiolactone
  作者：A. Chiaroni、C. Riche、S. Bouifraden、J.-P. Lavergne、P. Viallefont

  DOI：10.1107/s0108270196014461

  日期：1997.4.15

  The stereochemistry of (3R,2'S)-2'-N-dibenzylamino-1,2:5,6-di-O-isopropylidene-alpha-D-allofuranose-3-spiro-3'-propano-3-lactone, C28H33NO7, has been established, The three five-membered rings adopt envelope conformations, The spiropropiolactone ring is practically planar.
• Diastereoselective synthesis of glycosyl-α-aminoacids
  作者：Samira Bouifraden、Jean-Pierre Lavergne、Jean Martinez、Philippe Viallefont、Claude Riche

  DOI：10.1016/s0957-4166(97)00067-0

  日期：1997.3

  Asymmetric synthesis of various glycosyl-alpha-aminoacids is described. The approach involves the diastereoselective condensation of glycine enolates on the carbonyl in position 3 of the suitably protected alpha-D-ribohexafuranos-3-ulose. (C) 1997 Elsevier Science Ltd.