(S)-N-[(1R)-1-[(3aR,5R,6S,6aR)-2,2-dimethyl-6-phenylmethoxy-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]prop-2-enyl]-2-methylpropane-2-sulfinamide | 1353465-27-6

• 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: (S)-N-[(1R)-1-[(3aR,5R,6S,6aR)-2,2-dimethyl-6-phenylmethoxy-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]prop-2-enyl]-2-methylpropane-2-sulfinamide
• CAS: 1353465-27-6
• 化学式: C₂₁H₃₁NO₅S
• 分子量: 409.547
• InChiKey: RMAXWYZISCUTMR-GRIRAFEESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  85.2
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (S)-N-[(1R)-1-[(3aR,5R,6S,6aR)-2,2-dimethyl-6-phenylmethoxy-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]prop-2-enyl]-2-methylpropane-2-sulfinamide 在 盐酸 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 生成 3-O-benzyl-5,6,7-trideoxy-1,2-O-isopropylidene-5-amino-α-D-gluco-hept-6-enfuranose
  参考文献：
  名称：

  Unexpected highly diastereoconvergent Grignard additions to d-xylofuranose-derived t-butanesulfinyl aldimines

  摘要：

  Unexpected high levels of diastereoconvergence (dr >15:1) were observed in the addition of a series of Grignard reagents in THF to D-xylose-derived t-BS aldimines 2a,b affording (S-S,5R)- and (R-S,5R)-adducts. This anomaly was absent when using ethereal solutions of organometallic reagents, revealing the subtle solvent effects. This study illustrates the scope and limitations of N-t-BS imine chemistry in complex systems. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.11.002
• 作为产物：
  描述：

  3-O-苄基-1,2:5,6-O-双异丙叉-α-D-呋喃葡萄糖 在 盐酸 、 sodium periodate 、 水 、 碳酸氢钠 、 copper(II) sulfate 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 39.0h， 生成 (S)-N-[(1R)-1-[(3aR,5R,6S,6aR)-2,2-dimethyl-6-phenylmethoxy-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]prop-2-enyl]-2-methylpropane-2-sulfinamide
  参考文献：
  名称：

  Unexpected highly diastereoconvergent Grignard additions to d-xylofuranose-derived t-butanesulfinyl aldimines

  摘要：

  Unexpected high levels of diastereoconvergence (dr >15:1) were observed in the addition of a series of Grignard reagents in THF to D-xylose-derived t-BS aldimines 2a,b affording (S-S,5R)- and (R-S,5R)-adducts. This anomaly was absent when using ethereal solutions of organometallic reagents, revealing the subtle solvent effects. This study illustrates the scope and limitations of N-t-BS imine chemistry in complex systems. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.11.002

文献信息

• Unexpected highly diastereoconvergent Grignard additions to d-xylofuranose-derived t-butanesulfinyl aldimines
  作者：Bing Wang、Pei-Pei Zhang

  DOI：10.1016/j.tetlet.2011.11.002

  日期：2012.1

  Unexpected high levels of diastereoconvergence (dr >15:1) were observed in the addition of a series of Grignard reagents in THF to D-xylose-derived t-BS aldimines 2a,b affording (S-S,5R)- and (R-S,5R)-adducts. This anomaly was absent when using ethereal solutions of organometallic reagents, revealing the subtle solvent effects. This study illustrates the scope and limitations of N-t-BS imine chemistry in complex systems. (C) 2011 Elsevier Ltd. All rights reserved.