3,4,6-tri-O-acetyl-2-deoxy-2-phtalimido-α-D-galacto-pyranosyl bromide | 81704-03-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 3,4,6-tri-O-acetyl-2-deoxy-2-phtalimido-α-D-galacto-pyranosyl bromide
• 英文别名: 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-galactopyranosylbromide；tri-O-acetyl-2-deoxy-2-phthalimido-α-D-galactopyranosyl bromide；[(2R,3R,4R,5R,6R)-3,4-diacetyloxy-6-bromo-5-(1,3-dioxoisoindol-2-yl)oxan-2-yl]methyl acetate
• CAS: 81704-03-2
• 化学式: C₂₀H₂₀BrNO₉
• 分子量: 498.284
• InChiKey: GRDUQQNEXMJRRS-SFFUCWETSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  31
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  126
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  3,4,6-tri-O-acetyl-2-deoxy-2-phtalimido-α-D-galacto-pyranosyl bromide 在 甲醇 、 sodium methylate 、 silver trifluoromethanesulfonate 、 溶剂黄146 、 肼 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 为溶剂， 生成 8-Methoxycarbonyloctyl 2-acetamido-2-deoxy-β-D-galactopyranoside
  参考文献：
  名称：

  βGal(1→S-4)βGlcNAc-OR: A galactosidase-stable substrate for α(1→3)fucosyltransferase

  摘要：

  1'-4 Thio-N-acetyllactosamine was chemically synthesized as a galactosidase-stable substrate for alpha(1-->3)fucosyltransferase. The product of enzymatic fucose addition was confirmed to be the thio-Le X analog. (C) 1998 Elsevier Science Ltd. Air rights reserved.

  DOI：

  10.1016/s0960-894x(98)00552-6
• 作为产物：
  描述：

  D-(+)-galactosamine hydrochloride 在 氢溴酸 、 乙酸酐 、 溶剂黄146 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 51.0h， 生成 3,4,6-tri-O-acetyl-2-deoxy-2-phtalimido-α-D-galacto-pyranosyl bromide
  参考文献：
  名称：

  Detection of 210 kDa receptor protein for a leaf-movement factor by using novel photoaffinity probes

  摘要：

  Circadian rhythmic plant leaf-movement, called nyctinasty, is controlled by a time-course change in the internal concentration of the leaf-movement factor in the plant body. We revealed that specific binding proteins (210 and 180 kDa) for the leaf-movement factor, potassium lespedezate (1), are contained in the plasma membrane of the plant motor cell by using novel synthetic photoaffinity probes. These proteins are localized on the motor cell in the plant body, and would be potential receptors for the leaf-movement factor to control the leaf-movement. Our study is a rare successful result of the detection of membrane receptors by using a synthetic photoaffinity probe designed on a biologically active natural product. And these results also advance a guideline for probe design towards successful photoaffinity labeling. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.06.022

文献信息

• Conversion of p-methoxyphenyl glycosides into the corresponding glycosyl chlorides and bromides, and into thiophenyl glycosides
  作者：Zhiyuan Zhang、Göran Magnusson

  DOI：10.1016/s0008-6215(96)90118-4

  日期：1996.12

  Treatment of the pMP glycosides with acyl chlorides or bromides in the presence of various Lewis acids gave the corresponding glycosyl chlorides and bromides in 81-98% yield. Treatment of the acyl-protected pMP glycosides with thiophenol and boron trifluoride etherate gave the corresponding thioglycosides in 80-100% yield and high (> 20:1) beta/alpha selectivity. The stability of pMP glycosides was investigated

  使用硼从相应的1-O-乙酰基糖中制备对甲氧基苯基（pMP）β-D-吡喃葡萄糖苷（Glc，Gal，GlcNPhth，GalNPhth，GlcNTroc，Gal beta 4Glc，Gal alpha 4Gal），使用硼制得三氟化醚醚为助催化剂。在各种路易斯酸的存在下用酰氯或溴化物处理pMP糖苷得到相应的糖酰氯和溴化物，产率为81-98％。用硫酚和三氟化硼醚化物处理酰基保护的pMP糖苷，可以80-100％的收率和高（> 20：1）β/ alpha选择性获得相应的硫糖苷。针对一系列试剂研究了pMP糖苷的稳定性。
• Synthese der pentasaccharid-kette des forssman-antigens
  作者：Hans Paulsen、Almuth Bünsch

  DOI：10.1016/s0008-6215(00)81032-0

  日期：——

  ranosyl)-(1 leads to 3)-O-(6-O-acetyl-4-O-bebenzyl-2-deoxy-2-phthalimido-beta-D-galactopyranosyl)-(1 leads to 3)-6-O-acetyl-2,4-di-O-benzyl-alpha-D-galactopyranosyl bromide (40) (this was obtained through acetolysis of O-(6-O-acetyl-2-azido-3,4-di-O-benzoyl-2-deoxy-alpha-D-galactopyranosyl)-(1 leads to 3)-O-(6-O-acetyl-4-O-benzyl-2-deoxy-2-phthalimido-beta-D-galactopyranosyl)-(1 leads to 3)-1,6-anhydro-2

  Forssman抗原O-（2-acetamido-2-deoxy-alpha-D-galactopyranosyl）-（1的五糖链导致3）-O-（2-acetamido-2-deoxy-beta-D-galactopyranosyl） -（1导致3）-O-α-D-吡喃半乳糖-（1导致4）-O-β-D-吡喃半乳糖-（1导致4）-D-吡喃葡萄糖（46）通过嵌段合成法合成其中两个D-半乳糖残基之间形成了α-D-糖苷键。三糖O-（6-O-乙酰基-2-叠氮基3,4-二-O-苯甲酰基-2-脱氧-α-D-吡喃半乳糖基）-（1导致3）-O-（6-O-乙酰-4-O-苄基-2-脱氧-2-邻苯二甲酰亚胺-β-D-吡喃半乳糖基）-（1导致3）-6-O-乙酰基-2,4-二-O-苄基-α-D-吡喃半乳糖基溴化物（40）（通过乙酰分解O-（6-O-乙酰基-2-叠氮基3，4-二-O-苯甲酰基-2-脱氧-α-D-吡喃半乳糖
• A stereocontrolled total synthesis of a ganglio-ganglioside GM1b, IV3NeuAcαGgOse4Cer
  作者：Mamoru Sugimoto、Kazushige Fujikura、Shigeki Nunomura、Toshio Horisaki、Yukishige Ito、Tomoya Ogawa

  DOI：10.1016/s0040-4039(00)94561-1

  日期：1990.1

  A first total synthesis of ganglio ganglioside GM1b. α-D-NeupAc-(2→3)-β-D-Galp(1→3)-β-D-GalpNAc-(1→4)-β-D-Galp-(1→4)-β-D-Glcp-(1→1)-Cer, was achieved in a stereocontrolled manner.

  的第一全合成ganglio神经节苷脂GM1b。α-d-neu的p的Ac-（2→3）-β-d-Gal的p（1→3）-β-d-Gal的p NAc-（1→4）-β-d-Gal的p - （1→ 4）-β-d-GLC p - （1→1）-Cer，在一个立体控制的方式来实现。
• Synthesis of a novel bioactive photoaffinity probe based on a leaf-movement factor with potential high binding affinity to its receptor molecule
  作者：Tomohiko Fujii、Takanori Sugimoto、Shosuke Yamamura、Minoru Ueda

  DOI：10.1016/s0040-4039(03)00287-9

  日期：2003.3

  located in the pulvini of the plant. Some receptors of the leaf-movement factor should be involved in this biological event. We developed a novel photoaffinity probe (1) for the detection of receptor molecules. Probe compound 1 bears a photolabeling group on the 2′-position of the glycon moiety, which is near the potential binding site of the molecule with its receptor. This molecular design would be effective

  叶片运动因子与植物小叶植物中运动细胞的结合诱导了芥子叶运动。叶片运动因子的某些受体应参与此生物学事件。我们开发了一种新型的光亲和探针（1）用于检测受体分子。探针化合物1在糖苷部分的2'-位置带有一个光标记基团，该基团靠近该分子与其受体的潜在结合位点。这种分子设计对于提高光标记产率是有效的。
• Regio- and stereo-selective synthesis of ganglioside GM1b and some positional analogs
  作者：Hubli Prabhanjan、Akihiko Kameyama、Hideharu Ishida、Makoto Kiso、Akira Hasegawa

  DOI：10.1016/0008-6215(91)80011-b

  日期：1991.11

  Total syntheses of ganglioside GM1b (IV3NeuAcGgOse4Cer) and three of its positional analogs are described. Methyl O-(methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D- glycero-alpha-D-galacto-2-nonulopyranosylonate)- (2----3)-2,4,6-tri-O-benzoyl-1-thio-beta-D-galactopyranoside (7) and methyl O-(methyl 5- acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-alpha-D-galacto-2 -nonulopyranosylonate)-(2----6)-2

  描述了神经节苷脂GM1b（IV3NeuAcGgOse4Cer）及其三个位置类似物的总合成。O-（5-乙酰氨基-4,7,8,9-四-O-乙酰基-3,5-二甲氧基-D-甘油-α-D-半乳糖-2-壬基吡喃糖醛酸甲酯）-（2 ---- 3）-2,4,6-三-O-苯甲酰基-1-硫代-β-D-吡喃半乳糖苷（7）和甲基O-（甲基5-乙酰氨基-4,7,8,9-四-O-乙酰基-3,5-二脱氧-D-甘油-α-D-半乳糖-2-壬基吡喃磺酸盐）-（2 ---- 6）-2,4-二-O-苯甲酰基-3-O-苄基-1-硫代-β-D-吡喃半乳糖苷（8）是根据我们报道的方法制备的关键糖基供体。3,4,6-三-O-乙酰基-2-脱氧-2-邻苯二甲酰亚胺基-α-D-吡喃半乳糖基溴化物与2-（三甲基甲硅烷基）乙基O-（2,3,6-三-O-苄基- β-D-吡喃半乳糖基）-（1 ---- 4）-2,3,6-三-O-苄基-β-D-吡喃葡萄