6-C-phenyl-3,6-dideoxy-1,2-O-isopropylidene-α-D-allofuranose | 131013-17-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-C-phenyl-3,6-dideoxy-1,2-O-isopropylidene-α-D-allofuranose
• 英文别名: (1R)-1-[(3aR,5S,6aR)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-2-phenylethanol
• CAS: 131013-17-7
• 化学式: C₁₅H₂₀O₄
• 分子量: 264.321
• InChiKey: AQSOCWRQFSUTPI-XJFOESAGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.86
• 重原子数：
  19.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  47.92
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  6-C-phenyl-3,6-dideoxy-1,2-O-isopropylidene-α-D-allofuranose 在 吡啶 、 sodium azide 作用下， 以 二甲基亚砜 为溶剂， 反应 27.0h， 生成 6-C-phenyl-5-azido-3,5,6-trideoxy-1,2-O-isopropylidene-β-L-talofuranose
  参考文献：
  名称：

  Total synthesis of (+)-preussin, a novel antifungal agent

  摘要：

  The total synthesis of (+)-preussin, (2S,3S,5R)-1-methyl-5-nonyl-2-(phenylmethyl)-3-pyrrolidinol, was achieved by using D-glucose as the starting material. The key synthetic steps involved the sequential reduction and cyclization of azido triflate 6 to construct the pyrrolidine moiety 7 with the proper stereochemistry.

  DOI：

  10.1021/jo00003a040
• 作为产物：
  描述：

  (3aR,5S,6aR)-2,2-dimethyl-5-((R)-oxiran-2-yl)tetrahydrofuro[2,3-d][1,3]dioxole 、 phenylmagnesium chloride 在 copper(l) iodide 作用下， 以 四氢呋喃 为溶剂， 以100%的产率得到6-C-phenyl-3,6-dideoxy-1,2-O-isopropylidene-α-D-allofuranose
  参考文献：
  名称：

  Total synthesis of (+)-preussin, a novel antifungal agent

  摘要：

  The total synthesis of (+)-preussin, (2S,3S,5R)-1-methyl-5-nonyl-2-(phenylmethyl)-3-pyrrolidinol, was achieved by using D-glucose as the starting material. The key synthetic steps involved the sequential reduction and cyclization of azido triflate 6 to construct the pyrrolidine moiety 7 with the proper stereochemistry.

  DOI：

  10.1021/jo00003a040

文献信息

• PAK, CHWANG SIEK;LEE, GE HYEONG, J. ORG. CHEM., 56,(1991) N, C. 1128-1133
  作者：PAK, CHWANG SIEK、LEE, GE HYEONG

  DOI：——

  日期：——
• Total synthesis of (+)-preussin, a novel antifungal agent
  作者：Chwang Siek Pak、Ge Hyeong Lee

  DOI：10.1021/jo00003a040

  日期：1991.2

  The total synthesis of (+)-preussin, (2S,3S,5R)-1-methyl-5-nonyl-2-(phenylmethyl)-3-pyrrolidinol, was achieved by using D-glucose as the starting material. The key synthetic steps involved the sequential reduction and cyclization of azido triflate 6 to construct the pyrrolidine moiety 7 with the proper stereochemistry.