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 | 114262-28-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 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
• 英文别名: 2-[(2R,3R,4R,5S,6R)-5-[[(3aS,4R,6S,7R,7aR)-7-hydroxy-4-(hydroxymethyl)-2,2-dimethyl-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-6-yl]oxy]-4-hydroxy-6-(hydroxymethyl)-2-phenylmethoxyoxan-3-yl]isoindole-1,3-dione
• CAS: 114262-28-1
• 化学式: C₃₀H₃₅NO₁₂
• 分子量: 601.607
• InChiKey: MFDHWJLKJCAIFR-FDUXSHBXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.07
• 重原子数：
  43.0
• 可旋转键数：
  8.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  173.68
• 氢给体数：
  4.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  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 在 三氟乙酸 作用下， 以 吡啶 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 benzyl 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：

  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
• 作为产物：
  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

文献信息

• ALAIS, JOCELYNE;VEYRIERES, ALAIN, TETRAHEDRON LETT., 28,(1987) N 29, 3345-3348
  作者：ALAIS, JOCELYNE、VEYRIERES, ALAIN

  DOI：——

  日期：——