phenyl O-(2,6-di-O-benzoyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-(1-4)-2,6-di-O-benzoyl-1-thio-β-D-glucopyranoside | 195712-28-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: phenyl O-(2,6-di-O-benzoyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-(1-4)-2,6-di-O-benzoyl-1-thio-β-D-glucopyranoside
• 英文别名: [(3aS,4R,6S,7R,7aS)-7-benzoyloxy-6-[(2R,3S,4S,5R,6S)-5-benzoyloxy-2-(benzoyloxymethyl)-4-hydroxy-6-phenylsulfanyloxan-3-yl]oxy-2,2-dimethyl-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-4-yl]methyl benzoate
• CAS: 195712-28-8
• 化学式: C₄₉H₄₆O₁₄S
• 分子量: 890.962
• InChiKey: MOISWNFPPRGPEZ-GNHMMZCNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.1
• 重原子数：
  64
• 可旋转键数：
  18
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  197
• 氢给体数：
  1
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  苯基-2,3,4-三-O-苄基-1-硫代-β-L-岩藻吡喃糖苷 、 phenyl O-(2,6-di-O-benzoyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-(1-4)-2,6-di-O-benzoyl-1-thio-β-D-glucopyranoside 在 N-碘代丁二酰亚胺 、 三氟甲磺酸 作用下， 以 氯仿 为溶剂， 以83%的产率得到phenyl O-(2,6-di-O-benzoyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-(1-4)-O[(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1-3)]-2,6-di-O-benzoyl-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  A Highly Practical Synthesis of Sulfated Lewis X:  One-Pot, Two-Step Glycosylation Using “Armed/Disarmed” Coupling and Selective Benzoylation and Sulfation

  摘要：

  In spite of the several attractive biological activities of the Le(x), sLe(x), and sulfated Le(x) derivatives, there are still limitations in their practical syntheses. One of the most difficult problems is the many steps required for their syntheses. Therefore, we investigated simple constructions of the Le(x) analogs and succeeded in establishing highly practical syntheses of the Le(x) and sulfated Le(x) analogs. Especially, the ''armed/disarmed'' method allowed the first synthesis of Le(x) derivatives by a one-pot, two-step glycosylation. This synthetic strategy could be an applicable and useful method for oligosaccharide constructions of Le(x), sulfated Le(x), and other derivatives.

  DOI：

  10.1021/jo970076m
• 作为产物：
  描述：

  苯甲酰氯 、 phenyl (3,4-di-O-isopropylidene-β-D-galactopyranosyl)-(1->4)-1-thio-β-D-glucopyranoside 在 吡啶 作用下， 以 甲苯 为溶剂， 以77%的产率得到phenyl O-(2,6-di-O-benzoyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-(1-4)-2,6-di-O-benzoyl-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  A Highly Practical Synthesis of Sulfated Lewis X:  One-Pot, Two-Step Glycosylation Using “Armed/Disarmed” Coupling and Selective Benzoylation and Sulfation

  摘要：

  In spite of the several attractive biological activities of the Le(x), sLe(x), and sulfated Le(x) derivatives, there are still limitations in their practical syntheses. One of the most difficult problems is the many steps required for their syntheses. Therefore, we investigated simple constructions of the Le(x) analogs and succeeded in establishing highly practical syntheses of the Le(x) and sulfated Le(x) analogs. Especially, the ''armed/disarmed'' method allowed the first synthesis of Le(x) derivatives by a one-pot, two-step glycosylation. This synthetic strategy could be an applicable and useful method for oligosaccharide constructions of Le(x), sulfated Le(x), and other derivatives.

  DOI：

  10.1021/jo970076m

文献信息

• One-Pot Synthesis of Lewis X Oligosaccharide Derivatives Using "Armed-Disarmed" Coupling Method
  作者：Masahiro Yoshida、Takao Kiyoi、Takahiro Tsukida、Hirosato Kondo

  DOI：10.1080/07328309808002344

  日期：1998.5.1

  Abstract A stereocontrolled synthesis of Lex oligosaccharide derivatives using a facile one-pot, two-step glycosylation based on the “Armed-Disarmed” concept are described. The first coupling of phenyl O-(2,6-di-O-benzoyl-3,4-O-isopropylidene-β-D-galacto-pyranosyl)-(1→4)-2,6-di-O-benzoyl-1-thio-β-D-glucopyranoside (2) with phenyl 2,3,4-tri-O-benzyl-1-thio-β-L-fucopyranoside (3) using N-iodosuccinimide (N

  摘要描述了一种基于“武装解除”概念的简便的一锅两步糖基化立体控制合成Lex寡糖衍生物的方法。苯基O-（2,6-二-O-苯甲酰基-3,4-O-异亚丙基-β-D-半乳糖-吡喃糖基）-（1→4）-2,6-二-O-苯甲酰基的首次偶联使用N-碘代琥珀酰亚胺（NIS）-三氟甲磺酸（-1）将-1-硫代-β-D-吡喃葡萄糖苷（2）与苯基2,3,4-三-O-苄基-1-硫代-β-L-呋喃果糖苷（3）（ （TfOH）得到三糖（8），将其未经纯化而进行第二次缩合，用一些受体如2,4,6-三-O-苄基-β-D-D-吡喃半乳糖苷（4），2,6-二乙基乙基-O-苯甲酰基-β-D-吡喃半乳糖苷（5），乙基O-（2,6-二-O-苄基-β-D-吡喃半乳糖基）-（1→4）-2,3,6-tri-O -苄基-β-D-吡喃葡萄糖苷（6）和乙基O-（2,6-二-O-苯甲酰基-β-D-吡喃半乳糖基）-（1→4）-2,3，6-三-O-苄基
• Synthesis of Lewis X trisaccharide analogues in which glucose and rhamnose replace N-acetylglucosamine and fucose, respectively
  作者：Ari Asnani、France-Isabelle Auzanneau

  DOI：10.1016/s0008-6215(03)00053-3

  日期：2003.5

  Two analogues of the Le(x) trisaccharide, alpha-L-Fucp -(1 --> 3)-[beta-D-Galp -(1 --> 4)]-D-Glcp were synthesized as allyl glycosides. In these derivatives either only the N-acetylglucosamine is replaced by glucose or both the N-acetylglucosamine and the facosyl residue are replaced by glucose and rhamnose, respectively. Our synthetic scheme used armed beta-thiophenyl fuco- and rhamnoside glycosyl donors that were prepared anomerically pure from the corresponding alpha-glycosyl bromides. The protecting groups were chosen to allow access to the fully deprotected trisaccharides without reduction of the allyl glycosidic group. These analogues will be used as soluble antigens in binding experiments with anti-Le(x) antibodies and can also be conjugated to a carrier protein and used as immunogens. In the course of this synthetic work, we also describe the use of reversed-phase HPLC to purify key protected trisaccharide intermediates prior to their deprotection. (C) 2003 Elsevier Science Ltd. All rights reserved.