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 | 68124-17-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 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
• 英文别名: 3,6-di-O-acetyl-2-deoxy-2-phthalimido-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranosyl chloride；3,6-di-O-acetyl-4-O-(tetra-O-acetyl-β-D-galactopyranosyl)-2-deoxy-2-phthalimido-β-D-glucopyranosyl chloride；[(2R,3S,4S,5R,6S)-3,4,5-triacetyloxy-6-[(2R,3S,4R,5R,6S)-4-acetyloxy-2-(acetyloxymethyl)-6-chloro-5-(1,3-dioxoisoindol-2-yl)oxan-3-yl]oxyoxan-2-yl]methyl acetate
• CAS: 68124-17-4
• 化学式: C₃₂H₃₆ClNO₁₇
• 分子量: 742.087
• InChiKey: NBBJCTWPZFKHJK-OJTDSEIDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  51
• 可旋转键数：
  17
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  223
• 氢给体数：
  0
• 氢受体数：
  17

反应信息

• 作为反应物：
  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 对甲苯磺酸 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 9.5h， 生成 methyl 2-deoxy-4-O-(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：

  benzyl 3,6-di-O-benzyl-2-deoxy-2-phthalimido-beta-D-glucopyranoside 在 palladium on activated charcoal 盐酸 、 4 A molecular sieve 、 mercury dibromide 作用下， 以 四氢呋喃 、 吡啶 、 二氯甲烷 为溶剂， 反应 48.0h， 生成 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
  参考文献：
  名称：

  Synthesis of 3,6-di-O-acetyl-2-deoxy-2-phthalimido-4-O-(2,3,4,6-tetra-O-acetyl-β-d-galactopyranosyl)-β-d-glucopyranosyl chloride

  摘要：

  DOI：

  10.1016/s0008-6215(00)80526-1

文献信息

• 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......
• Ligand Recognition by E-Selectin: Synthesis, Inhibitory Activity and Conformational Analysis of Bivalent Sialyl Lewis x Analogs
  作者：Shawn A. DeFrees、Winfried Kosch、William Way、James C. Paulson、Subramanian Sabesan、Randall L. Halcomb、Dee-Hua Huang、Yoshitaka Ichikawa、Chi-Huey Wong

  DOI：10.1021/ja00106a008

  日期：1995.1

  Several sialyl Lewis x dimers anchored onto a galactose template or attached to 1,4-butanediol or 1,5-pentanediol have been prepared chemoenzymatically and evaluated as inhibitors of E-selectin-mediated cell adhesion. Two monosaccharide units were simultaneously incorporated (i.e., Gal, NeuAc, Fuc) by a glycosyltransferase into a chemically synthesized core structure containing GlcNAc and Gal. Each of the galactose-anchored dimers had higher activity than the sialyl Lewis x pentasaccharide la, with the general trend being 3,6-linked > 2,3 greater than or equal to 4,6 greater than or equal to 2,6 monomer. The dimers linked to butanediol or pentanediol showed the same level of activity as the pentasaccharide monomer. Conformational analysis of these dimers with NMR indicated that each sialyl Lewis x domain of the dimers retains the same conformation as the monomer. The differences in activity of the dimers most likely derive from differences in the relative orientation and distance between the monomer domains, suggesting the importance of the linker used in the preparation of dimers.
• Block synthesis of a hexasaccharide hapten of i blood group antigen
  作者：Jocelyne Alais、Alain Veyrieres

  DOI：10.1016/s0040-4039(00)88402-6

  日期：1983.1
• Syntheses of a series of lacto-N-neotetraose clusters using a carbosilane dendrimer scaffold
  作者：Akihiro Yamada、Ken Hatano、Tetsuo Koyama、Koji Matsuoka、Yasuaki Esumi、Daiyo Terunuma

  DOI：10.1016/j.carres.2005.11.037

  日期：2006.3

  4-Pentenyl (2,3,4,6-tetra-O-acetyl-beta-(D)-galactopyranosyl)-(1 -> 4)-(3,6-di-O-acetyl-2-deoxy-2-phthalimido-beta-(D)-glucopyranosyl)-( 1 -> 3)-(2,6-di-O-benzoyl-beta-(D)-gatactopyranosyl)-(1 -> 4)-2,3,6-tri-O-benzoyl-beta-(D)-glucopyranoside (4) was synthesized by regio-selective glycosylation of 4-pentenyl (2,6,-di-O-benzoyl-beta-(D)-galactopyranosyl)-(1 -> 4)-2,3,6-tri-O-benzoyl-beta-(D)-glueopyranoside and (2,3,4,6-tetra-O-acetyl-beta-(D)-galactopyranosyl)-(1 -> 4)-3,6-di-O-acetyl-2-deoxy-2-phthalimido-beta-(D)-glucopyranosyl chloride. By conversion of the protecting groups followed by thioacetylation, 4 was transformed into the corresponding lacto-N-neotetraose derivative, 5-(acetylthio)pentenyl (2,3,4,6-tetra-O-acetyl-beta-(D)-galactopyranosyl)-(1 -> 4)-O-(3,6-di-O-acetyl-2-acetamido-2-deoxy-beta-(D)-glucopyranosyl)-(1 -> 3)-(2,4,6-di-O-acetyl-beta-(D)-galactopyranosyl)-(1 -> 4)-2,3,6-tri-O-acetyl-beta-(D)-glucopyranoside (6). The lacto-N-neotetraose derivative 6 was introduced into carbosilane dendrimer cores of three shapes, and three kinds of new carbosilane dendrimers peripherally functionalized by lacto-N-neotetraose were obtained. (c) 2005 Elsevier Ltd. All rights reserved.
• Glycosylation of lactose. Synthesis of methyl O-(2-acetamido-2-deoxy-β-d-glucopyranosyl)-(1→3)-O-β-d-galactopyranosyl-(1→4)-β-d-glucopyranoside and methyl O-β-d-galactopyranosyl-(1→4)-O-(2-acetamido-2-deoxy-β-d-glucopyranosyl)-(1→3)-O-β-d-galactopyranosyl- (1→4)-β-d-glucopyranoside
  作者：Aurelio Maranduba、Alain Veyrières

  DOI：10.1016/s0008-6215(00)90785-7

  日期：1985.1