O-(2,3,4,6-Tetra-O-acetyl-β-D-galactopyranosyl)-(1->4)-3,6-di-O-acetyl-2-desoxy-2-phthalimido-β-D-glucopyranose | 81243-76-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: O-(2,3,4,6-Tetra-O-acetyl-β-D-galactopyranosyl)-(1->4)-3,6-di-O-acetyl-2-desoxy-2-phthalimido-β-D-glucopyranose
• 英文别名: 3,6-di-O-acetyl-2-deoxy-2-phtalimido-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranose；3,6-di-O-acetyl-2-deoxy-2-phthalimido-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranose
• CAS: 81243-76-7
• 化学式: C₃₂H₃₇NO₁₈
• 分子量: 723.642
• InChiKey: LKHGUINPLXEXRZ-QCOZAFKPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.67
• 重原子数：
  51.0
• 可旋转键数：
  11.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  243.1
• 氢给体数：
  1.0
• 氢受体数：
  18.0

反应信息

• 作为反应物：
  描述：

  O-(2,3,4,6-Tetra-O-acetyl-β-D-galactopyranosyl)-(1->4)-3,6-di-O-acetyl-2-desoxy-2-phthalimido-β-D-glucopyranose 在 2,4,6-三甲基吡啶 、 silver trifluoroacetate Vilsmeier reagent 作用下， 生成 methyl O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->4)-O-(3,6-di-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->3)-O-(2,6-di-O-acetyl-β-D-galactopyranosyl)-(1->4)-3,6-di-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranoside
  参考文献：
  名称：

  Block synthesis of a hexasaccharide hapten of i blood group antigen

  摘要：

  DOI：

  10.1016/s0040-4039(00)88402-6
• 作为产物：
  描述：

  2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1→4)-1,3,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranoside 在 乙酸肼 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以84%的产率得到O-(2,3,4,6-Tetra-O-acetyl-β-D-galactopyranosyl)-(1->4)-3,6-di-O-acetyl-2-desoxy-2-phthalimido-β-D-glucopyranose
  参考文献：
  名称：

  乳糖的糖基化：涉及具有I型血活性的糖脂的生物合成中涉及的分支寡糖的合成

  摘要：

  制备4-O-（2-O-苯甲酰基-4,6-O-亚苄基-β-D-吡喃半乳糖基）-2,3,6-三-O-苯甲酰基-β-D-吡喃葡萄糖苷（2）从甲基β-乳糖苷四个步骤。晶体2是用于合成衍生自乳糖的支链寡糖的便利底物。首先，使用N-邻苯二甲酰氨基糖的三氯乙酰亚胺酸酯在3'-位进行高产率的糖基化，然后在除去亚苄基后在6'-位进行。因此，将3,4,6-三-O-乙酰基-2-脱氧-2-邻苯二甲酰亚胺-β-D-吡喃葡萄糖基三氯乙酰亚氨酸酯用于两个连续的糖基化反应中，同时用于三醇9的同时分解，从而导致每个序列变为支链四糖β-D-GlcpNAc-（1 ---- 3）-[β-D-GlcpNAc-（1 ---- 6）]-β-D-Galp-（1 ---- 4） -β-D-GlcOMe。用3进行相似的糖基化，

  DOI：

  10.1016/s0008-6215(00)90333-1

文献信息

• Anwendung des trichloracetimidatverfahrens auf 2-desoxy-2-phthalimido-d-glucose-derivative. Synthese von oligosacchariden der “Core-Region” von O-glycoproteinen des mucin-typs
  作者：Gerhard Grundler、Richard R. Schmidt

  DOI：10.1016/s0008-6215(00)90772-9

  日期：1985.1

  Abstract N -Phthaloyl derivatives of 2-acetamido-2-deoxy- d -glucose having OH-1 free treated with trichloroacetonitrile and sodium hydride gave the corresponding O -(β- d -glycosyl)trichloroacetimidates which in the presence of diethyl ether·borontrifluoride, led selectively with alcohols to β- d -glycosides. This procedure was applied to the synthesis of oligosaccharides from the core region of mucine-type

  摘要经三氯乙腈和氢化钠处理的OH-1游离基的2-乙酰氨基-2-脱氧-d-葡萄糖的N-邻苯二甲酰基衍生物，在二乙醚·三氟化硼的存在下，给出了相应的O-（β-d-糖基）三氯乙亚氨酸酯。 ，用醇选择性地导致β-d-糖苷。该方法被用于从鼠型O-糖蛋白的核心区域合成寡糖。因此，β-d-Gal p-（1→4）-β-d-Glc p NAc-（1→3）-d -GalNAc和β-d-Gal-（1→4）-β-d-Glc获得了p NAc- [β-d-Glc p NAc-（（1→3）]-d-GalNAc。
• Chemical-Enzymatic Synthesis of A Branched Hexasaccharide Fragment of Type Ia Group B<i>Streptococcus</i>Capsular Polysaccharide
  作者：Wei Zou、Harold J. Jennings

  DOI：10.1080/07328309608005699

  日期：1996.11

  of type Ia group B streptococcal polysaccharide, α-NeuAc(2→3)-β-D-Gal(1→4)-β-D-GlcNAc(1→3)-[β-D-Glc(1→4)]-β-D-Gal(1→4)-β-D-Glc-OMe (13), has been synthesized by chemical-enzymatic procedures. Chemical synthesis of a pentasaccharide, β-D-Gal(1→4)-β-D-GlcNAc(1→3)-[β-D-Glc(1→4)]-β-D-Gal(1→4)-β-D-Glc-OMe (12), was achieved from glycosyl donor, 4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-3,6-di-O

  Ia B型链球菌多糖的分支六糖片段α-NeuAc（2→3）-β-D-Gal（1→4）-β-D-GlcNAc（1→3）-[β-D-Glc（ 1→4）]-β-D-Gal（1→4）-β-D-Glc-OMe（13），已通过化学酶法合成。五糖β-D-Gal（1→4）-β-D-GlcNAc（1→3）-[β-D-Glc（1→4）]-β-D-Gal（1→4）的化学合成）-β-D-Glc-OMe（12）是从糖基供体4- O-（2,3,4,6-tetra- O-乙酰基-β-D-吡喃半乳糖基）-3,6-di获得的- ø -乙酰基-2-脱氧-2-苯二甲酰亚-β-d-D-吡喃葡萄糖三氯乙酰亚胺酯（9），和受体，甲基ø - （2,3,4,6-四- ö乙酰基β-d-D-吡喃葡萄糖基） -（1→4）-O-（2,6-二-O-苄基-β-D-吡喃半乳糖基）-（1→4）-2,3,6-三-O-苄基-β-D-吡喃葡萄糖苷（6），通过
• Syntheses of linear tetra-, hexa-, and octa-saccharide fragments of the i-blood group active poly-(N-acetyl-lactosamine) series. Blockwise methods for the synthesis of repetitive oligosaccharide sequences
  作者：Jocelyne Alais、Alain Veyrie`res

  DOI：10.1016/0008-6215(90)80002-k

  日期：1990.10

  N-Phthaloylation of lactosamine gave various glycosyl donors (beta-chloride, beta-trichloroacetimidate) and glycosyl acceptors (3',4'-diol). Coupling of the chloride with a methyl beta-D-glycoside led to the tetrasaccharide fragment, beta-D-Galp-(1----4)-beta-D-GlcpNac-(1----3)-beta-D-Galp-(1----4)- beta-D-GlcpNAcOMe. Acetolysis of the protected tetrasaccharide, followed by treatment with hydrogen chloride, gave a tetrasaccharide chloride which was coupled with the methyl beta-glycoside of lactosamine. A hexasaccharide fragment, [beta-D-Galp-(1----4)-beta-D-GlcpNAc-(1----3)]2-beta-D-Galp-(1----4)-bet a- D-GlcpNAcOMe, was thus obtained by this ("n + 1") method. A more efficient ("n + n") method was applied for the synthesis of an octasaccharide fragment, [beta-D-Galp-(1----4)-beta-D-GlcpNAc-(1----3)]3-beta-D-Galp- (1----4)-beta-D-GlcpNAcOMe (38), where di- and tetra-saccharide intermediates having a 3,4-O-isopropylidene-beta-D-galactopyranosyl nonreducing terminal group and a benzyl beta-D-glycoside group were precursors, either as glycosyl donors (beta-trichloroacetimidates) or glycosyl acceptors (3,4-diols as nonreducing terminal groups). Thus, doubling the length of the repetitive oligosaccharide sequence could be efficiently accomplished at each glycosylation step.
• Schmidt, Richard R.; Grundler, Gerhard, Angewandte Chemie, 1983, vol. 95, # 10, p. 805 - 806
  作者：Schmidt, Richard R.、Grundler, Gerhard

  DOI：——

  日期：——