(R,R,R,R)-4-benzyloxy-5-[N-benzyl-N-(α-methylbenzyl)amino]-6-(triisopropylsilyloxy)hex-1-en-3-ol | 1429412-85-0

• 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: (R,R,R,R)-4-benzyloxy-5-[N-benzyl-N-(α-methylbenzyl)amino]-6-(triisopropylsilyloxy)hex-1-en-3-ol
• 英文别名: (3R,4R,5R)-5-[benzyl-[(1R)-1-phenylethyl]amino]-4-phenylmethoxy-6-tri(propan-2-yl)silyloxyhex-1-en-3-ol
• CAS: 1429412-85-0
• 化学式: C₃₇H₅₃NO₃Si
• 分子量: 587.918
• InChiKey: FKRQNOGLAGKPFA-MCNAWRSPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.94
• 重原子数：
  42
• 可旋转键数：
  17
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  41.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R,R,R,R)-4-benzyloxy-5-[N-benzyl-N-(α-methylbenzyl)amino]-6-(triisopropylsilyloxy)hex-1-en-3-ol 在 silver tetrafluoroborate 、 碘 、 碳酸氢钠 、 potassium carbonate 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 49.0h， 生成 (R,R,R,R)-N(1)-benzyl-2-[(triisopropylsilyloxy)methyl]-3-benzyloxy-4,5-dihydroxypiperidine
  参考文献：
  名称：

  Asymmetric Syntheses of (−)-1-Deoxymannojirimycin and (+)-1-Deoxyallonojirimycin via a Ring-Expansion Approach

  摘要：

  The asymmetric syntheses of (-)-1-deoxymannojirimycin and (+)-1-deoxyallonojirimycin are described herein. The ring-closing iodoamination of two epimeric bishomoallylic amines to give the corresponding 5-iodomethylpyrrolidines was followed by in situ ring-expansion to give two diastereoisomerically pure (>99:1 dr) cyclic carbonates. Subsequent deprotection gave (-)-1-deoxymannojirimycin and (+)-1-deoxyallonojirimycin as single diastereoisomers in 7.4 and 3.3% overall yield, respectively, from commercially available starting materials.

  DOI：

  10.1021/ol400735z
• 作为产物：
  描述：

  (2R,3R)-3-[benzyl-[(1R)-1-phenylethyl]amino]-2-phenylmethoxy-4-tri(propan-2-yl)silyloxybutan-1-ol 在 草酰氯 、 二甲基亚砜 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 17.0h， 生成 (R,R,R,R)-4-benzyloxy-5-[N-benzyl-N-(α-methylbenzyl)amino]-6-(triisopropylsilyloxy)hex-1-en-3-ol
  参考文献：
  名称：

  Asymmetric Syntheses of (−)-1-Deoxymannojirimycin and (+)-1-Deoxyallonojirimycin via a Ring-Expansion Approach

  摘要：

  The asymmetric syntheses of (-)-1-deoxymannojirimycin and (+)-1-deoxyallonojirimycin are described herein. The ring-closing iodoamination of two epimeric bishomoallylic amines to give the corresponding 5-iodomethylpyrrolidines was followed by in situ ring-expansion to give two diastereoisomerically pure (>99:1 dr) cyclic carbonates. Subsequent deprotection gave (-)-1-deoxymannojirimycin and (+)-1-deoxyallonojirimycin as single diastereoisomers in 7.4 and 3.3% overall yield, respectively, from commercially available starting materials.

  DOI：

  10.1021/ol400735z

文献信息

• Asymmetric syntheses of 2,5-dideoxy-2,5-imino-d-glucitol [(+)-DGDP] and 1,2,5-trideoxy-1-amino-2,5-imino-d-glucitol [(+)-ADGDP]
  作者：Stephen G. Davies、Aude L.A. Figuccia、Ai M. Fletcher、Paul M. Roberts、James E. Thomson

  DOI：10.1016/j.tet.2014.03.100

  日期：2014.6

  The asymmetric syntheses of 2,5-dideoxy-2,5-imino-D-glucitol [(+)-DGDP] and 1,2,5-trideoxy-1-amino-2,5-imino-D-glucitol [(+)-ADGDP] were achieved via the ring-closing iodoamination of an enantiopure bishomoallylic amine, followed by functionalisation of the resultant iodomethyl substituted pyrrolidine. In the case of (+)-DGDP, formation of the corresponding aziridinium ion followed by regioselective ring-opening with H2O gave the desired hydroxymethyl substituted pyrrolidine as a single diastereoisomer (>99:1 dr), with subsequent deprotection giving (+)-DGDP in good yield. Whereas in the case of (+)-ADGDP, displacement of iodide with NaN3 proved to be optimal, giving (+)-ADGDP in good yield after reduction and deprotection. (C) 2014 Elsevier Ltd. All rights reserved.
• Asymmetric Syntheses of (−)-1-Deoxymannojirimycin and (+)-1-Deoxyallonojirimycin via a Ring-Expansion Approach
  作者：Stephen G. Davies、Aude L. A. Figuccia、Ai M. Fletcher、Paul M. Roberts、James E. Thomson

  DOI：10.1021/ol400735z

  日期：2013.4.19

  The asymmetric syntheses of (-)-1-deoxymannojirimycin and (+)-1-deoxyallonojirimycin are described herein. The ring-closing iodoamination of two epimeric bishomoallylic amines to give the corresponding 5-iodomethylpyrrolidines was followed by in situ ring-expansion to give two diastereoisomerically pure (>99:1 dr) cyclic carbonates. Subsequent deprotection gave (-)-1-deoxymannojirimycin and (+)-1-deoxyallonojirimycin as single diastereoisomers in 7.4 and 3.3% overall yield, respectively, from commercially available starting materials.