1,2,4,6-tetra-O-benzoyl-β-D-glucopyranose | 72076-17-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1,2,4,6-tetra-O-benzoyl-β-D-glucopyranose
• 英文别名: 1,2,4,6-tetra-O-benzoyl-β-D-glucopyranoside；[(2R,3S,4S,5R,6S)-3,5,6-tribenzoyloxy-4-hydroxyoxan-2-yl]methyl benzoate
• CAS: 72076-17-6
• 化学式: C₃₄H₂₈O₁₀
• 分子量: 596.59
• InChiKey: OKBFAFHPSRQSGG-YNQPRHMTSA-N

物化性质

• 沸点：
  762.1±60.0 °C(Predicted)
• 密度：
  1.38±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  44
• 可旋转键数：
  13
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  135
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  1,2,4,6-tetra-O-benzoyl-β-D-glucopyranose 在 palladium on activated charcoal 2,4,6-三甲基吡啶 、 三氟甲磺酸三甲基硅酯 、 3 A molecular sieve 、 氢溴酸 、 氢气 、 silver trifluoromethanesulfonate 、 碳酸氢钠 、 硫脲 作用下， 以 甲醇 、 二氯甲烷 、 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 反应 71.58h， 生成 O-{2,3-di-O-benzoyl-4,6-O-[(R)-1-methoxycarbonyl(ethylidene)]-α-D-galactopyranosyl}-(1->3)-2,4,6-tri-O-benzoyl-β-D-glucopyranosyl-(1->3)-2-O-benzoyl-4,6-O-[(S)-1-methoxycarbonyl(ethylidene)]-α-D-glucopyranose
  参考文献：
  名称：

  Rhizobial saccharides. Part. 4. Unusual Reactivity of Pyruvated Glycosyl Donors during construction of rhizobial exopolysaccharide fragments

  摘要：

  Two pyruvated galactosyl donors, 2,3-di-O-benzoyl-4,6-0-[1-(R)-methoxycarbonyl(ethylidene)]-alpha-D-galactopyranosyl chloride (6) and trichloroacetimidate 13, were coupled to position 3 of suitably protected mono and disaccharide benzyl glucoside accepters. For both donors, an unusual high content of the alpha-(1-->3)-linked products was obtained. The corresponding beta-(1-->3)-linked di- and trisaccharides are related to exopolysaccharides of Rhizobium leguminosarum.

  DOI：

  10.1002/prac.19973390196
• 作为产物：
  描述：

  3-O-苄基-1,2:5,6-O-双异丙叉-α-D-呋喃葡萄糖 在 4-二甲氨基吡啶 、 10 wt% Pd(OH)2 on carbon 、 氢气 、 三甲胺 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 50.0h， 生成 1,2,4,6-tetra-O-benzoyl-β-D-glucopyranose
  参考文献：
  名称：

  [EN] ACIDIC DYSTROGLYCAN OLIGOSACCHARIDE COMPOUND AND METHOD FOR MAKING SAME
  [FR] COMPOSÉ OLIGOSACCHARIDIQUE DE DYSTROGLYCANE ACIDE ET PROCÉDÉ DE PRÉPARATION ASSOCIÉ

  摘要：

  一种合成的二甘酸酰肽寡糖，包括公式(I)，其中重复的二糖基序列由葡萄糖醛酸（GlcA）和木糖（Xyl）组成，具有定义的糖基连接GlcA-β-（1→3）-Xyl-α-（1→3）-GlcA；其中合成的二甘酸酰肽寡糖的任一端可与化学或生物载体或支持物连接；其中非还原端（II）可与任何可修饰羟基功能的寡糖或基团连接；还原端可与任何标签、寡糖或可修改羟基功能的物质连接。

  公开号：

  WO2019136399A1

文献信息

• Radiosynthesis of 18F-labeled d-allose
  作者：Hiroyuki Yamamoto、Kenji Wada、Jun Toyohara、Tetsuro Tago、Masanobu Ibaraki、Toshibumi Kinoshita、Yuka Yamamoto、Yoshihiro Nishiyama、Nobuyuki Kudomi

  DOI：10.1016/j.carres.2019.107827

  日期：2019.12

  suitable synthetic procedures for novel rare sugars of d-allose that are 18F-labeled at the C-3 and C-6 positions and the preparation of the appropriate labeling precursors. The goal is to facilitate in vivo, noninvasive positron emission tomography (PET) investigation of the behavior of rare sugar analogs of d-allose in organs. We found five precursors that were practical for labeling, three for

  稀有糖定义为自然界中存在的单糖，但数量有限。d-Allose是一种稀有糖，据报道具有某些独特的生理作用。本研究描述了合适的合成程序，用于在C-3和C-6位置18F标记的d-阿糖新稀有糖以及适当标记前体的制备。目的是促进体内无创正电子发射断层扫描（PET）研究器官中d-阿糖的稀有糖类似物的行为。我们发现了五种适用于标记的前体，三种用于3-deoxy-3- [18F]氟-d-阿洛糖（[18F] 3FDA），两种用于6-脱氧-6- [18F]氟-d-阿洛糖（ [18F] 6FDA）。通过手动操作合成，前体1,2,4，[18F] 3FDA的最高放射化学转化率为75％，6-四-O-乙酰基-3-O-三氟甲磺酰基-β-d-吡喃葡萄糖和69％的[18F] 6FDA用1,2,3,4-四-O-乙酰基-6-O-三氟甲磺酰基的前体-β-d-丙戊糖。此外，还研究了使用自动合成仪的[18F] 3FDA和[18F] 6
• 無担体放射性ハロゲン標識化デオキシハロゲノ−Ｄ−アロース、非放射性デオキシフルオロ−Ｄ−アロース、およびそれらの前駆体、ならびにそれらの製造方法
  申请人：国立大学法人 香川大学

  公开号：JP2018030823A

  公开（公告）日：2018-03-01

  【課題】 D-アロース骨格を有する新たな放射性ハロゲン標識化物質、その製造方法等を提供する。【解決手段】 本発明の放射性ハロゲン標識化デオキシハロゲノ‐D-アロース誘導体は、下記一般式（１）もしくは下記一般式（２）で表される化合物またはその塩であることを特徴とする。前記式（１）および（２）において、Ｘは、ハロゲンの放射性同位元素であり、例えば、18Fである。【化１】 【選択図】なし

  【问题】提供具有D-阿罗斯骨架的新放射性卤素标记化合物及其制造方法等。 【解决方案】本发明的放射性卤素标记化脱氧卤代-D-阿罗斯衍生物是指以下一般式（1）或以下一般式（2）所表示的化合物或其盐。在上述式（1）和（2）中，X是放射性卤素同位素，例如18F。 【化学式1】 【选择图】无
• Synthetic studies toward pyruvate acetal containing saccharides. Synthesis of the carbohydrate part of the Mycobacterium smegmatis pentasaccharide glycolipid and fragments thereof for the preparation of neoantigens
  作者：Thomas Ziegler、Elisabeth Eckhardt、Veronique Birault

  DOI：10.1021/jo00057a021

  日期：1993.2

  A series of 2,3-di-O-benzoyl-4,6-O-[(S)-1-(methoxycarbonyl)ethylidene]-D-glucopyranosyl donors (beta-phenylthio 3, bromide 4, alpha-chloride 5, beta-fluoride 6, and trichloroacetimidate 7) were prepared from the corresponding alpha-allyl glucoside 1 via the deallylated glucose 2 and were tested in glycosylation reactions with methanol to give the pyruvylated methyl glucosides 8 and 9 and with methyl 2,4,6-tri-O-benzoyl-beta-D-glucopyranoside 10 to give the disaccharide 11. Best results with respect to yield and beta-selectivity of the coupling were achieved with imidate 7. Thus, the 2-O-benzoyl-4,6-O-[(S)-1-(methoxycarbonyl)ethylidene]-3-O-methyl-D-glucopyranosyl trichloroacetimidate 14 was prepared from its benzyl glucoside 12 and used for the synthesis of fragments related to the Mycobacterium smegmatis lipopentasaccharide. Trimethylsilyl trifluoromethanesulfonate-mediated condensation of 14, 5-[(benzyloxycarbonyl)amino]pentanol, and 10, respectively, followed by deblocking of the products 15 and 17 gave the pyruvylated aminopentyl glucoside 16 and methyl laminaribioside 18. Treatment of 17 with dichloromethyl methyl ether gave the laminaribiosyl chloride 19, coupling of which with protected 5-aminopentanol gave 20 also obtained from 14 and the monosaccharide nucleophile 26. The trisaccharide 5-aminopentyl glycoside fragment 42 was prepared by first coupling of 14 and benzyl 2-O-benzoyl-4,6-O-[(S)-1-(methoxycarbonyl)ethylidene]-alpha-D-glucopyranoside 30 that was converted to the bispyruvylated laminaribiose imidate 33, followed by condensation with thioglycoside 38 obtainable in four steps from 1,2,4,6-tetra-O-acetyl-3-O-benzyl-beta-D-glucopyranose to give the trisaccharide ethyl thioglycoside 40. Next, NIS-mediated condensation of 40 and 5-[(benzyloxycarbonyl)amino]pentanol followed by deblocking gave 42. Pentasaccharide 45 was similarly prepared from 40 and hepta-O-benzoyltrehalose 43 to give first the blocked saccharide 44, deblocking of which afforded the target pentasaccharide.
• UNIQUE PHENYL ETHER TYPE BIFLAVONOIDS, ZIZYFLAVOSIDES A AND B WITH BIOMIMETIC SYNTHESIS FOR ZIZYFLAVOSIDE A
  作者：Mahmoud Mostafa、Tomihisa Ohta、Fumihide Takano

  DOI：10.3987/com-10-12002

  日期：——

  During our investigation of Zizyphus spina-christi (L.) Willd. leaves for anti-inflammatory activity, eight compounds were characterized. Two are new phenyl ether type biflavonoids, which were assigned as zizyflavosides A (1) and B (2). The structures of 1 and 2 were determined by spectroscopic analyses including ID, 2D NMR and MS spectroscopic and chemical data. The other isolated compounds were known flavonoids kaempferol-3-O-rutinoside (5), quercetin-3-O-rutinoside (6), 3`,5`-di-C-beta-D-glucosylphloretine (7), quercetin-3-O-[beta-D-xylosyl-(1 -> 2)-alpha-L-rhamnoside]-4`-O-alpha-L-rhamnoside (8), epiafzelechin (9) and quercetin-3-O-[beta-D-xylosyl-(1 -> 2)-alpha-L-rhamnoside] (10). Zizyflavoside A was synthesized from quercetin-3-O-rutinoside and kaempferol-3-O-rutinoside using laccase as an enzyme and this biomimetic synthesis could be indication to its biosynthetic pathway.