(R)-4-(iodomethyl)-2-phenyl-2-oxazoline | 236388-58-2

• 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: (R)-4-(iodomethyl)-2-phenyl-2-oxazoline
• 英文别名: (4R)-4-(iodomethyl)-2-phenyl-4,5-dihydro-1,3-oxazole
• CAS: 236388-58-2
• 化学式: C₁₀H₁₀INO
• 分子量: 287.1
• InChiKey: VTWWULPAPTZQSG-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  21.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R)-4-(iodomethyl)-2-phenyl-2-oxazoline 在 盐酸 、 4-二甲氨基吡啶 、 正丁基锂 、 4 Angstroem MS 、 sodium acetate 、 对甲苯磺酰肼 作用下， 以 四氢呋喃 、 吡啶 、 正己烷 为溶剂， 反应 37.0h， 生成 Acetic acid (S)-2-benzoylamino-4-((2S,3S,4R,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-butyl ester
  参考文献：
  名称：

  Synthesis of β-d-Galactosyl Ceramide Methylene Isostere

  摘要：

  The methylene isostere of the glycosphingolipid beta-D-galactosyl N-palmitoyl C-18 ceramide has been synthesized by a linear reaction sequence starting from a beta-linked D-galactopyranosyl aldehyde. First, this sugar aldehyde was converted into a methylenephosphorane which in turn was coupled with N-Boc serinal acetonide. The double bond of the resulting olefin was reduced and the oxazolidine ring was cleaved and oxidized to give a C-glycosyl N-Boc alpha-amino butanal (three-carbon chain elongation). Then, an additional C-15 carbon chain was installed by addition of lithium 1-pentadecyne to the above glycosyl amino aldehyde. The syn/anti ratio (70:30) of the resulting mixture of amino alcohols was reversed (5:95) by an oxidation-reduction sequence to achieve the same stereochemistry as in the hydrophilic head of D-erythro-sphingosines. The major product was subjected to the reduction of the triple bond with LiAlH4 to give the olefin with E geometry. Finally the N-amide group was installed by reaction with palmitoyl chloride and the O-benzyl protective groups of the sugar moiety were removed by treatment with lithium in liquid NH3-THF. The final product was characterized as the O-acetyl derivative.

  DOI：

  10.1021/jo990398l
• 作为产物：
  描述：

  (R)-4-carbomethoxy-2-phenyl-oxazoline 在 咪唑 、 lithium aluminium tetrahydride 、 碘 、 三苯基膦 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 0.75h， 生成 (R)-4-(iodomethyl)-2-phenyl-2-oxazoline
  参考文献：
  名称：

  Synthesis of β-d-Galactosyl Ceramide Methylene Isostere

  摘要：

  The methylene isostere of the glycosphingolipid beta-D-galactosyl N-palmitoyl C-18 ceramide has been synthesized by a linear reaction sequence starting from a beta-linked D-galactopyranosyl aldehyde. First, this sugar aldehyde was converted into a methylenephosphorane which in turn was coupled with N-Boc serinal acetonide. The double bond of the resulting olefin was reduced and the oxazolidine ring was cleaved and oxidized to give a C-glycosyl N-Boc alpha-amino butanal (three-carbon chain elongation). Then, an additional C-15 carbon chain was installed by addition of lithium 1-pentadecyne to the above glycosyl amino aldehyde. The syn/anti ratio (70:30) of the resulting mixture of amino alcohols was reversed (5:95) by an oxidation-reduction sequence to achieve the same stereochemistry as in the hydrophilic head of D-erythro-sphingosines. The major product was subjected to the reduction of the triple bond with LiAlH4 to give the olefin with E geometry. Finally the N-amide group was installed by reaction with palmitoyl chloride and the O-benzyl protective groups of the sugar moiety were removed by treatment with lithium in liquid NH3-THF. The final product was characterized as the O-acetyl derivative.

  DOI：

  10.1021/jo990398l