benzyl 3,6-di-O-acetyl-4-O-(tetra-O-acetyl-β-D-galactopyranosyl)-2-deoxy-2-phthalimido-β-D-glucopyranoside | 81243-74-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl 3,6-di-O-acetyl-4-O-(tetra-O-acetyl-β-D-galactopyranosyl)-2-deoxy-2-phthalimido-β-D-glucopyranoside
• CAS: 81243-74-5
• 化学式: C₃₉H₄₃NO₁₈
• 分子量: 813.766
• InChiKey: RFECKMUVGVEKQI-RFKPKHNMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.56
• 重原子数：
  58.0
• 可旋转键数：
  14.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.49
• 拓扑面积：
  232.1
• 氢给体数：
  0.0
• 氢受体数：
  18.0

反应信息

• 作为反应物：
  描述：

  benzyl 3,6-di-O-acetyl-4-O-(tetra-O-acetyl-β-D-galactopyranosyl)-2-deoxy-2-phthalimido-β-D-glucopyranoside 在 sodium methylate 、 对甲苯磺酸 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 8.0h， 生成 2-[(2R,3R,4R,5S,6R)-2-Benzyloxy-4-hydroxy-5-((3aS,4R,6S,7R,7aR)-7-hydroxy-4-hydroxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-6-hydroxymethyl-tetrahydro-pyran-3-yl]-isoindole-1,3-dione
  参考文献：
  名称：

  Synthesis of an octasaccharide fragment of the polylactosamine series by a blockwise approach

  摘要：

  DOI：

  10.1016/s0040-4039(00)95508-4
• 作为产物：
  描述：

  1,3,6-tri-O-acetyl-2-deoxy-2-phthalimido-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α-D-glucopyranose 在 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 作用下， 以 吡啶 、 二氯甲烷 为溶剂， 反应 17.0h， 生成 benzyl 3,6-di-O-acetyl-4-O-(tetra-O-acetyl-β-D-galactopyranosyl)-2-deoxy-2-phthalimido-β-D-glucopyranoside
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1016/0008-6215(90)80002-k

文献信息

• Chemoenzymatic Synthesis of Sialyl Sulfo-Oligosaccharides as Potent Siglec-8 Ligands via Transglycosylation Catalyzed by Keratanase II
  作者：Shiori Yuge、Ayaka Tateishi、Keiji Numata、Masashi Ohmae

  DOI：10.1021/acs.biomac.1c01289

  日期：2022.1.10

  Sialyl type-II sulfo-oligosaccharides are gaining much attention as bioactive ligands for Siglecs. In this study, we have achieved the first synthesis of sialyl type-II sulfo-oligosaccharides chemoenzymatically by utilizing the transglycosylation activity of keratanase II. The oxazoline derivative of α(2→3)-sialylated 6,6′-di-sulfo-LacNAc (3) was newly designed as the glycosyl donor for enzymatic transglycosylation

  唾液酸 II 型磺基寡糖作为 Siglecs 的生物活性配体受到了广泛关注。在这项研究中，我们首次利用角质酶 II 的转糖基化活性化学酶促合成唾液酸 II 型磺基寡糖。α(2→3)-唾液酸化的 6,6'-二磺基-LacNAc ( 3 ) 的恶唑啉衍生物被新设计为酶促转糖基化的糖基供体。Keratanase II用两种糖基受体 6-磺基-Lewis X 和 6,6'-二-磺基-LacNAc 衍生物有效催化3的转糖基化，提供唾液酸磺基六糖 ( 1 ) 和唾液酸磺基五糖 ( 2 )产率分别为 86% 和 95%。产品1和与具有K的 α(2→3)-唾液酸化 6,6'-二磺基-Lewis X 的已知配体相比，图2对 Siglec-8 的亲和力更高，K D分别为70 和 25 μmol·L –1 D 185 μmol·L –1。因此，本研究不仅将推动Siglec-8生物学的研究，还将推动对具有各种微结构的唾液酸磺基寡糖功能的探索。
• Syntheses of derivatives of <i>N</i>-acetyl-<scp>D</scp>-lactosamine from <scp>D</scp>-lactal hexaacetate. Hexa-<i>O</i>-acetyl-2-deoxy-2-phthalimido-β-<scp>D</scp>-lactosyl chloride
  作者：R. U. Lemieux、S. Z. Abbas、M. H. Burzynska、R. M. Ratcliffe

  DOI：10.1139/v82-011

  日期：1982.1.1

  Two reaction routes are presented for the preparation of hexa-O-acetyl-2-deoxy-2-phthalimido-β-D-lactosyl chloride (7) from lactal hexaacetate (1). One route involves, in the first stage, reaction ...

  提出了两种反应路线，用于从乳酸六乙酸酯 (1) 制备六-O-乙酰基-2-脱氧-2-邻苯二甲酰亚胺-β-D-乳糖酰氯 (7)。一个途径涉及，在第一阶段，反应......
• Wong, Ting C.; Lemieux, Raymond U., Canadian Journal of Chemistry, 1984, vol. 62, p. 1207 - 1213
  作者：Wong, Ting C.、Lemieux, Raymond U.

  DOI：——

  日期：——