allyl 2,6-di-O-benzyl-3-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-α-D-galactopyranoside | 282089-17-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: allyl 2,6-di-O-benzyl-3-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-α-D-galactopyranoside
• 英文别名: Bn(-2)[Bn(-3)][Bn(-4)][Bn(-6)]Gal(a1-3)[Bn(-2)][Bn(-6)]Gal(a)-O-allyl；(2R,3S,4S,5R,6S)-5-phenylmethoxy-2-(phenylmethoxymethyl)-6-prop-2-enoxy-4-[(2R,3R,4S,5S,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxyoxan-3-ol
• CAS: 282089-17-2
• 化学式: C₅₇H₆₂O₁₁
• 分子量: 923.113
• InChiKey: ZTHCFPUCHGRYEY-MIVXDHBWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.1
• 重原子数：
  68
• 可旋转键数：
  25
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  113
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  allyl 2,6-di-O-benzyl-3-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-α-D-galactopyranoside 在 palladium dichloride 作用下， 以 甲醇 为溶剂， 生成 2,6-di-O-benzyl-3-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-D-galactopyranose
  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：

  烯丙基-Α-D-吡喃半乳糖苷 在 氢氧化钾 、 4 A molecular sieve 、 三氟化硼乙醚 、 四正辛基溴化铵 、 potassium carbonate 、 palladium dichloride 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 176.5h， 生成 allyl 2,6-di-O-benzyl-3-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-α-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.