methyl 4-O-(β-D-galactopyranosyl)-2-deoxy-2-phthalimido-β-D-glucopyranoside | 86733-50-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 4-O-(β-D-galactopyranosyl)-2-deoxy-2-phthalimido-β-D-glucopyranoside
• 英文别名: methyl 2-deoxy-4-O-β-D-galactopyranosyl-2-phthalimido-β-D-glucopyranoside；methyl β-N-phthaloyllactosaminide
• CAS: 86733-50-8
• 化学式: C₂₁H₂₇NO₁₂
• 分子量: 485.445
• InChiKey: YEZOPIUEFYMGDO-UTHPUQQFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.44
• 重原子数：
  34.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  195.68
• 氢给体数：
  6.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  methyl 4-O-(β-D-galactopyranosyl)-2-deoxy-2-phthalimido-β-D-glucopyranoside 在 对甲苯磺酸 作用下， 以 吡啶 为溶剂， 反应 3.5h， 生成 methyl 3,6-di-O-acetyl-2-deoxy-4-O-(2,6-di-O-acetyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-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：

  2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl(1<*>4)-2-deoxy-2-phthalimido-3,6-di-O-acetyl-β-D-glucopyranosyl chloride 在 calcium sulfate 、 sodium methylate 、 mercury dichloride 、 mercury(II) oxide 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 methyl 4-O-(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

• Regioselective mono-o-alkylation of disaccharide glycosides through their dibutylstannylene complexes
  作者：Jocelyne Alais、Aurelio Maranduba、Alain Veyrieres

  DOI：10.1016/s0040-4039(00)81931-0

  日期：1983.1

  Allyl β--Acetyllactosaminide, methyl β--phthalogllactosaminide. and methyl β-lactoside give with high selectivity and good yields the corresponding 3′-O-allyl derivatives by reaction of their dibutylstannylene complexes with allyl bromide and tetrabutylammonium bromide.

  烯丙基β--乙酰半乳糖胺，甲基β--邻苯二甲酰半乳糖胺。通过其二丁基亚锡配合物与烯丙基溴和四丁基溴化铵的反应，甲基β-乳糖苷具有高的选择性和良好的产率，得到了相应的3'-O-烯丙基衍生物。
• 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：——