O-(2,3,4,6-Tetra-O-acetyl-β-D-galactopyranosyl)-(1->4)-3,6-di-O-acetyl-2-desoxy-2-phthalimido-D-glucopyranose | 81243-75-6

• 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-D-glucopyranose
• 英文别名: O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->4)-3,6-di-O-acetyl-2-deoxy-2-phthalimido-D-glucopyranose；3,6-di-O-acetyl-4-O-(tetra-O-acetyl-β-D-galactopyranosyl)-2-deoxy-2-phthalimido-α,β-D-glucopyranose；2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-3,6-di-O-acetyl-2-deoxy-2-phthalimido-D-glucopyranose；3,6-di-O-acetyl-2-deoxy-2-phthalimido-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-D-glucopyranose；4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-3,6-di-O-acetyl-2-deoxy-2-phthalimido-D-glucopyranose；AcLacNPhth-1-OH；[(2R,3S,4R,5R)-4-acetyloxy-5-(1,3-dioxoisoindol-2-yl)-6-hydroxy-3-[(2S,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyoxan-2-yl]methyl acetate
• CAS: 81243-75-6；81243-76-7；91852-38-9
• 化学式: C₃₂H₃₇NO₁₈
• 分子量: 723.642
• InChiKey: LKHGUINPLXEXRZ-DKECSUQMSA-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-D-glucopyranose 在 三氟化硼乙醚 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成 4-methoxyphenyl 2,3,4,6-tetra-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：

  Rapid Access to an Orthogonally Protected Lewis X Derivative: An Important Building Block for Synthesis of Lewis Antigens

  摘要：

  系统地制备了具有一组正交保护基团的新型路易斯X衍生物1。有效利用乳糖胺中氨基和羟基的保护基团能够在 C3 和 C2' 处形成二醇衍生物。 1-硫代-1-岩藻糖苷供体与二醇衍生物的糖苷化优选在 C3 羟基上进行，从而预先产生 1。化合物 1 是轻松组装 Lewis X 相关碳水化合物表位的关键构建模块。

  DOI：

  10.1246/cl.2011.438
• 作为产物：
  描述：

  benzyl 3,6-di-O-acetyl-4-O-(tetra-O-acetyl-β-D-galactopyranosyl)-2-deoxy-2-phthalimido-α-D-glucopyranoside 在 palladium on activated charcoal 氢气 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 24.0h， 以60%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-D-glucopyranose
  参考文献：
  名称：

  从 D-内酰胺六乙酸酯合成 N-乙酰-D-乳糖胺衍生物。六-O-乙酰基-2-脱氧-2-邻苯二甲酰亚胺-β-D-乳糖酰氯

  摘要：

  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......

  DOI：

  10.1139/v82-011

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。
• Synthesis of a heptasaccharide hapten related to a bi-antennary glycan chain of human chorionic gonadotropin of a choriocarcinoma patient. A convergent approach
  作者：Khalid K. Sadozai、Tomoo Nukada、Yukishige Ito、Yoshiaki Nakahara、Tomoya Ogawa、Akira Kobata

  DOI：10.1016/0008-6215(86)85063-7

  日期：1986.12

  Synthesis of the heptasaccharide hapten 8-methoxycarbonyloctyl O-beta-D-galactopyranosyl-(1----4)-O-(2-acetamido-2-deoxy-beta-D- glucopyranosyl)-(1----2)-O-[beta-D-galactopyranosyl-(1----4)-O-(2-acetam ido-2- deoxy-beta-D-glucopyranosyl)-(1----4)]-O-alpha-D-mannopyranosyl-(1----3) -O- [alpha-D-mannopyranosyl-(1----6)]-beta-D-mannopyranoside is described, by use of the known, protected glycosyl acceptor

  6-二-O-苄基-α-D-甘露聚糖三氯乙酰亚氨酯（5）和相应的氟化物7，依次由5,6-烯丙基3,6-二-O-苄基-α-D-制备甘露吡喃糖苷的总产率分别为35％和22％。在模型实验中，关键的糖基供体5和7也用简单的糖基受体8-乙氧基羰基辛醇处理，得到8-甲氧基羰基辛基O-β-D-吡喃半乳糖基-（1-4）-O-（2-乙酰氨基-2-脱氧-β-D-吡喃葡萄糖基）-（1 ---- 2）-O-β-D-吡喃半乳糖基-（1 ---- 4）-O-（2-乙酰胺基-2-脱氧-β-D-吡喃葡萄糖基）-（1 ---- 4）]-α（和β）-D-甘露吡喃糖苷。
• Studies on carbohydrates XX. Synthesis of hexasaccharide containing lactosamine unit using glycosyl trichloroacetates as glycosyl donors
  作者：Xiao Xiang Zhu、Ping Yu Ding、Meng Shen Cai

  DOI：10.1016/0040-4039(96)01989-2

  日期：1996.11

  O-Glycosyl trichloroacetate, a stable and readily obtained intermediate, was activated as a highly reactive glycosyl donor upon treatment with acid and coupled with the acceptor to afford complex glycosides with high stereoselectivity.

  稳定且易于获得的中间体O-糖基三氯乙酸酯，经酸处理后被活化为高反应性糖基供体，并与受体偶联，从而提供了具有高立体选择性的复合糖苷。
• Ammann, Helene; Dupuis, Gilles, Canadian Journal of Chemistry, 1988, vol. 66, p. 1651 - 1655
  作者：Ammann, Helene、Dupuis, Gilles

  DOI：——

  日期：——
• Synthesis of tumor-associated saccharides via O-glycosyl trichloroacetic
  作者：Xiao-Xiang Zhu、Ping Yu Ding、Meng-Shen Cai

  DOI：10.1016/0957-4166(96)00373-4

  日期：1996.10

  The trichloroacetic method was employed to synthesize di- and hexa-saccharides. O-glycosyl trichloroacetic, a stable and readily obtained intermediate, was activated to give a highly reactive glycosyl donor upon treatment with acid and coupled with the acceptor to afford complex glycosides with high stereoselectivity and in good yield. Two free hexasaccharides will be used to explore the possible prevention of metastatic spread. Copyright (C) 1996 Published by Elsevier Science Ltd