(3'S,4'R)-3'-aminononadec-5'-yn-4'-olyl 2,3,4-tetra-O-benzyl-β-C-D-galactopyranoside | 236388-65-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3'S,4'R)-3'-aminononadec-5'-yn-4'-olyl 2,3,4-tetra-O-benzyl-β-C-D-galactopyranoside
• 英文别名: (3S,4R)-3-amino-1-[(2S,3S,4R,5S,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]nonadec-5-yn-4-ol
• CAS: 236388-65-1
• 化学式: C₅₃H₇₁NO₆
• 分子量: 818.15
• InChiKey: BHMOBJJDVWEHDF-AIZCCOHXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.8
• 重原子数：
  60
• 可旋转键数：
  28
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.51
• 拓扑面积：
  92.4
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (3'S,4'R)-3'-aminononadec-5'-yn-4'-olyl 2,3,4-tetra-O-benzyl-β-C-D-galactopyranoside 在 lithium aluminium tetrahydride 作用下， 以 乙二醇二甲醚 为溶剂， 反应 3.0h， 以65%的产率得到(3'S,4'R)-3'-amino-(E)-nonadec-5'-en-4'-olyl 2,3,4-tetra-O-benzyl-β-C-D-galactopyranoside
  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：

  1-十五炔 在 盐酸 、 正丁基锂 、 4 Angstroem MS 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 正己烷 、 水 为溶剂， 生成 (3'S,4'R)-3'-aminononadec-5'-yn-4'-olyl 2,3,4-tetra-O-benzyl-β-C-D-galactopyranoside
  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

文献信息

• Synthesis of β-<scp>d</scp>-Galactosyl Ceramide Methylene Isostere
  作者：Alessandro Dondoni、Daniela Perrone、Elisa Turturici

  DOI：10.1021/jo990398l

  日期：1999.7.1

  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.