(2S),(3'R)-3'-N-dibenzyl-1,2:5,6-di-O-isopropylidene-α-D-allofuranos-3-spiropropiolactone | 188854-32-2

• 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: (2S),(3'R)-3'-N-dibenzyl-1,2:5,6-di-O-isopropylidene-α-D-allofuranos-3-spiropropiolactone
• 英文别名: (3R),(2'S)-2'-N-Dibenzylamino-1,2:5,6-diisopropylidene-alpha-D-allofuranos-3-spiro-beta-propiolactone；(3'S,3aR,5R,6R,6aR)-3'-(dibenzylamino)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethylspiro[5,6a-dihydro-3aH-furo[2,3-d][1,3]dioxole-6,4'-oxetane]-2'-one
• CAS: 188854-32-2
• 化学式: C₂₈H₃₃NO₇
• 分子量: 495.573
• InChiKey: AJIPHDAECYLCLU-QUCBLMSRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  36
• 可旋转键数：
  6
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  75.7
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (2S),(3'R)-3'-N-dibenzyl-1,2:5,6-di-O-isopropylidene-α-D-allofuranos-3-spiropropiolactone 在 氨 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以95%的产率得到(S)-2-Dibenzylamino-2-[(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]-acetamide
  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
• 作为产物：
  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 methyl ester 在 sodium hydroxide 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 29.0h， 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：

  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

• Synthesis of New Glycopeptides from the α-D-Allofuranos-3-Spiropropiolactone
  作者：Bouifraden, Samira、Lavergne, Jean-Pierre、Martinez, Jean、Viallefont, Philippe

  DOI：10.1080/00397919708005914

  日期：1997.11

  alpha-D-allofuranas-3-spiropropiolactone 3 was coupled with differents amino esters in the presence of DMAP. This reaction lead to glycopeptides with complete control of chirality.
• (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.