allyl 3,4-O-cyclohexylidene-2,6-di-O-benzyl-β-D-galactopyranoside | 282089-16-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧吡喃
• 英文名称: allyl 3,4-O-cyclohexylidene-2,6-di-O-benzyl-β-D-galactopyranoside
• 英文别名: (3aS,4R,6R,7R,7aS)-7-phenylmethoxy-4-(phenylmethoxymethyl)-6-prop-2-enoxyspiro[4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-2,1'-cyclohexane]
• CAS: 282089-16-1
• 化学式: C₂₉H₃₆O₆
• 分子量: 480.601
• InChiKey: TVLXWOPPMXXKFH-QBROEMLDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  35
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  allyl 3,4-O-cyclohexylidene-2,6-di-O-benzyl-β-D-galactopyranoside 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以98%的产率得到allyl 2,6-di-O-benzyl-β-D-galactopyranoside
  参考文献：
  名称：

  A novel synthesis of α-d-Galp-(1→3)-β-d-Galp-1-O-(CH2)3NH2, its linkage to activated matrices and absorption of anti-αGal xenoantibodies by affinity columns

  摘要：

  Pig organs transplanted into primates are rapidly rejected because of the interaction between Ga1 alpha(1-->3)Ga1 epitopes carried by the graft and natural antibodies (anti-alpha Ga1 antibodies) present in the blood of the recipient. This report describes a simplified synthesis of the xenogeneic disaccharide and its linkage to activated gel matrices. The digalactosides alpha-D-Ga1p-(1-->3)-alpha,beta-D-Ga1p-OAll were synthesized by the condensation of the trichloroacetimidoyl 2,3,4,6-tetra-O-benzyl-beta-D-galactopyranoside donor with the 3,4-unprotected allyl 2,6-di-O-benzyl-alpha- or beta-D-galactopyranoside acceptor precursor. Deallylation and hydrogenolysis led to the free digalactoside, whereas hydrogenolysis alone resulted in the 1-O-propyl digalactoside. Both products were tested by inhibition ELISA of natural anti-Ga1 alpha(1-->3)Ga1 antibodies. The alpha-D-Ga1p-(1-->3)-beta-D-Ga1p-OPr was found to be the best inhibitor. Thus, the allyl group of the partially benzylated alpha-D-Ga1p-(1-->3)-beta-D-Ga1p-OAll was engineered, via the hydroxy-, the tosyloxy- and the azidopropyl intermediates, into an aminopropyl group amenable to binding to N-hydroxysuccinimide-activated agarose gel matrices in order to obtain specific immunoabsorption columns. Columns made of gel substituted with 5 mu mol of disaccharide per milliliter were found efficient for the immunoabsorption of anti-alpha Ga1 antibodies from human plasma. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(00)00010-0
• 作为产物：
  描述：

  allyl β-D-galactopyranoside 在 氢氧化钾 、 硫酸 、 四正辛基溴化铵 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 89.0h， 生成 allyl 3,4-O-cyclohexylidene-2,6-di-O-benzyl-β-D-galactopyranoside
  参考文献：
  名称：

  A novel synthesis of α-d-Galp-(1→3)-β-d-Galp-1-O-(CH2)3NH2, its linkage to activated matrices and absorption of anti-αGal xenoantibodies by affinity columns

  摘要：

  Pig organs transplanted into primates are rapidly rejected because of the interaction between Ga1 alpha(1-->3)Ga1 epitopes carried by the graft and natural antibodies (anti-alpha Ga1 antibodies) present in the blood of the recipient. This report describes a simplified synthesis of the xenogeneic disaccharide and its linkage to activated gel matrices. The digalactosides alpha-D-Ga1p-(1-->3)-alpha,beta-D-Ga1p-OAll were synthesized by the condensation of the trichloroacetimidoyl 2,3,4,6-tetra-O-benzyl-beta-D-galactopyranoside donor with the 3,4-unprotected allyl 2,6-di-O-benzyl-alpha- or beta-D-galactopyranoside acceptor precursor. Deallylation and hydrogenolysis led to the free digalactoside, whereas hydrogenolysis alone resulted in the 1-O-propyl digalactoside. Both products were tested by inhibition ELISA of natural anti-Ga1 alpha(1-->3)Ga1 antibodies. The alpha-D-Ga1p-(1-->3)-beta-D-Ga1p-OPr was found to be the best inhibitor. Thus, the allyl group of the partially benzylated alpha-D-Ga1p-(1-->3)-beta-D-Ga1p-OAll was engineered, via the hydroxy-, the tosyloxy- and the azidopropyl intermediates, into an aminopropyl group amenable to binding to N-hydroxysuccinimide-activated agarose gel matrices in order to obtain specific immunoabsorption columns. Columns made of gel substituted with 5 mu mol of disaccharide per milliliter were found efficient for the immunoabsorption of anti-alpha Ga1 antibodies from human plasma. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(00)00010-0

文献信息

• A novel synthesis of α-d-Galp-(1→3)-β-d-Galp-1-O-(CH2)3NH2, its linkage to activated matrices and absorption of anti-αGal xenoantibodies by affinity columns
  作者：Jérôme Liaigre、Didier Dubreuil、Jean-Paul Pradère、Jean-François Bouhours

  DOI：10.1016/s0008-6215(00)00010-0

  日期：2000.5

  Pig organs transplanted into primates are rapidly rejected because of the interaction between Ga1 alpha(1-->3)Ga1 epitopes carried by the graft and natural antibodies (anti-alpha Ga1 antibodies) present in the blood of the recipient. This report describes a simplified synthesis of the xenogeneic disaccharide and its linkage to activated gel matrices. The digalactosides alpha-D-Ga1p-(1-->3)-alpha,beta-D-Ga1p-OAll were synthesized by the condensation of the trichloroacetimidoyl 2,3,4,6-tetra-O-benzyl-beta-D-galactopyranoside donor with the 3,4-unprotected allyl 2,6-di-O-benzyl-alpha- or beta-D-galactopyranoside acceptor precursor. Deallylation and hydrogenolysis led to the free digalactoside, whereas hydrogenolysis alone resulted in the 1-O-propyl digalactoside. Both products were tested by inhibition ELISA of natural anti-Ga1 alpha(1-->3)Ga1 antibodies. The alpha-D-Ga1p-(1-->3)-beta-D-Ga1p-OPr was found to be the best inhibitor. Thus, the allyl group of the partially benzylated alpha-D-Ga1p-(1-->3)-beta-D-Ga1p-OAll was engineered, via the hydroxy-, the tosyloxy- and the azidopropyl intermediates, into an aminopropyl group amenable to binding to N-hydroxysuccinimide-activated agarose gel matrices in order to obtain specific immunoabsorption columns. Columns made of gel substituted with 5 mu mol of disaccharide per milliliter were found efficient for the immunoabsorption of anti-alpha Ga1 antibodies from human plasma. (C) 2000 Elsevier Science Ltd. All rights reserved.