1,2,3,6-O-四乙酰-BETA-D-葡萄糖 | 27086-15-3

• 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
• 中文名称: 1,2,3,6-O-四乙酰-BETA-D-葡萄糖
• 英文名称: 1,2,3,6-tetra-O-acetyl-β-D-glucopyranose
• 英文别名: (2S,3R,4S,5R,6R)-6-(Acetoxymethyl)-5-hydroxytetrahydro-2H-pyran-2,3,4-triyl triacetate；[(2R,3R,4S,5R,6S)-4,5,6-triacetyloxy-3-hydroxyoxan-2-yl]methyl acetate
• CAS: 27086-15-3
• 化学式: C₁₄H₂₀O₁₀
• 分子量: 348.307
• InChiKey: QYCFXXCSGBEENZ-RKQHYHRCSA-N

物化性质

• 熔点：
  131-132 °C
• 沸点：
  433.8±45.0 °C(Predicted)
• 密度：
  1.33±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 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：

  1,2,3,6-O-四乙酰-BETA-D-葡萄糖 生成 4-O-methyl-D-glucopyranose
  参考文献：
  名称：

  Koizumi, Kyoko; Utamura, Toshiko, Chemical and pharmaceutical bulletin, 1981, vol. 29, # 10, p. 2776 - 2784

  摘要：

  DOI：
• 作为产物：
  描述：

  (2R,3R,4S,5S,6R)-6-(trityloxymethyl)oxane-2,3,4,5-tetrol 在 吡啶 、 三氟乙酸 作用下， 以 溶剂黄146 为溶剂， 反应 1.33h， 生成 1,2,3,6-O-四乙酰-BETA-D-葡萄糖
  参考文献：
  名称：

  Utamura, Toshiko; Kuromatsu, Keiko; Suwa, Kiyoko, Chemical and pharmaceutical bulletin, 1986, vol. 34, p. 2341 - 2353

  摘要：

  DOI：

文献信息

• Synthesis of azido-deoxy and amino-deoxy glycosides and glycosyl fluorides for screening of glycosidase libraries and assembly of substituted glycosides
  作者：Hong-Ming Chen、Stephen G. Withers

  DOI：10.1016/j.carres.2018.07.007

  日期：2018.9

  useful tools in the probing of biological systems as well as in the assembly of libraries of derivatives using click chemistry or simple amine coupling approaches. A collection of methylumbelliferyl glycosides of various azido- and amino-deoxy sugar derivatives of glucose, galactose and xylose was synthesised via azide displacement of the corresponding triflate derivatives and subsequent modification.

  叠氮化物和胺取代的糖在探测生物系统以及使用点击化学或简单的胺偶联方法组装衍生物库中可能是有用的工具。通过叠氮化物置换相应的三氟甲磺酸衍生物并随后进行修饰，合成了葡萄糖，半乳糖和木糖的各种叠氮基和氨基脱氧糖衍生物的甲基伞形糖苷苷。这些化合物将在高通量筛选中用作底物，以鉴定可加工此类修饰糖的糖苷酶。还合成了每种修饰糖的α-糖基氟衍生物，以用作衍生自筛选中鉴定的酶的糖合酶底物。
• THE ALPHA AND BETA 1,3,4,6-TETRAACETYL-<scp>D</scp>-GLUCOPYRANOSES AND THEIR CHLOROACETYL DERIVATIVES
  作者：R. U. Lemieux、G. Huber

  DOI：10.1139/v53-136

  日期：1953.11.1

  Reaction of 3,4,6-triacetyl-β-D-glucopyranosyl chloride with silver acetate in acetic acid gave 1,3,4,6-tetraacetyl-α-D-glucopyranose, m.p. 97–98 °C., [α]_D + 145° (chloroform). 3,4,6,-Triacetyl-α-D-glucopyrartosyl chloride, m.p. 93–94 °C., [α]_D + 185° (chloroform), prepared from the β-anomer by isomerization in acetone, with silver acetate in acetic acid gave 1,3,4,6-tetraacetyl-β-D-glucopyranose, m.p. 137–138 °C., [α]_D + 26° (chloroform). The structures of these glucose tetraacetates were established by the interconversion of chloroacetyl derivatives.

  3,4,6-三乙酰基-β-D-葡萄糖吡喃基氯化物与醋酸银在冰醋酸中反应得到1,3,4,6-四乙酰基-α-D-葡萄糖吡喃糖，熔点97-98°C，[α]D +145°（氯仿）。3,4,6-三乙酰基-α-D-葡萄糖吡喃基氯化物，熔点93-94°C，[α]D +185°（氯仿），由β异构体在丙酮中异构化制备，与醋酸银在冰醋酸中反应得到1,3,4,6-四乙酰基-β-D-葡萄糖吡喃糖，熔点137-138°C，[α]D +26°（氯仿）。这些葡萄糖四乙酰基的结构是通过氯乙酰衍生物的相互转化确定的。
• A new method of orthoesterification, under kinetic control, at non-anomeric positions. Application to the d-glucose and d-mannose series and selective hydrolysis of the corresponding orthoesters
  作者：Mohamed Bouchra、Pierre Calinaud、Jacques Gelas

  DOI：10.1016/0008-6215(94)00306-z

  日期：1995.2

  Abstract The reaction of ketene acetals with d -glucose, d -mannose, and their methyl glycosides is described as a new route to unusual cyclic orthoesters (at non anomeric positions). The reaction proceeds by preferential attack of the reagent on the primary hydroxyl group. The synthesis of strained rings (2,3-diequatorial orthoester) is possible. The resulting methoxyethylidene derivatives are very sensitive

  摘要乙烯酮缩醛与d-葡萄糖，d-甘露糖及其甲基糖苷的反应被描述为一种通往不寻常环状原酸酯（在非异头位置）的新途径。反应通过试剂对伯羟基的优先攻击而进行。可以合成应变环（2,3-二季基原酸酯）。所得的甲氧基亚乙基衍生物对水解非常敏感，并且温和的条件导致羟基乙酸酯是可能用于碳水化合物合成的中间体。
• Selective deprotection of trityl group on carbohydrate by microflow reaction inhibiting migration of acetyl group
  作者：Atsushi Miyagawa、Ryusuke Tomita、Kenta Kurimoto、Hatsuo Yamamura

  DOI：10.1080/00397911.2016.1156703

  日期：2016.3.18

  ABSTRACT The trityl group is an important and useful protecting group for primary hydroxy groups on carbohydrates. However, during deprotection, neighboring acetyl groups can easily migrate to the deprotected hydroxy groups. Hence, deprotection of trityl groups was optimized using a microreactor with regard to flow rate, reagent concentration, reaction time, and substrate concentration. The optimized

  摘要 三苯甲基是碳水化合物上伯羟基的重要且有用的保护基团。然而，在脱保护过程中，相邻的乙酰基很容易迁移到脱保护的羟基上。因此，使用微反应器在流速、试剂浓度、反应时间和底物浓度方面优化三苯甲基的脱保护。优化的微流反应条件抑制了迁移，可应用于大规模反应和其他底物。图形概要
• Synthesis of uniformly deuterated<i>n</i>-dodecyl-<i>β</i>-<scp>d</scp>-maltoside (<i>d</i>₃₉-DDM) for solubilization of membrane proteins in TROSY NMR experiments
  作者：Kazumi Hiruma-Shimizu、Arnout P. Kalverda、Peter J. F. Henderson、Steve W. Homans、Simon G. Patching

  DOI：10.1002/jlcr.3249

  日期：2014.12

  This work reports the first synthesis of uniformly deuterated n-dodecyl-β-d-maltoside (d39-DDM). DDM is a mild non-ionic detergent often used in the extraction and purification of membrane proteins and for solubilizing them in experimental studies of their structure, dynamics and binding of ligands. We required d39-DDM for solubilizing large α-helical membrane proteins in samples for [15N–1H]TROSY (transverse relaxation-optimized spectroscopy) NMR experiments to achieve the highest sensitivity and best resolved spectra possible. Our synthesis of d39-DDM used d7-d-glucose and d25-n-dodecanol to introduce deuterium labelling into both the maltoside and dodecyl moieties, respectively. Two glucose molecules, one converted to a glycosyl acceptor with a free C4 hydroxyl group and one converted to a glycosyl donor substituted at C1 with a bromine in the α-configuration, were coupled together with an α(1 → 4) glycosidic bond to give maltose, which was then coupled with n-dodecanol by its substitution of a C1 bromine in the α-configuration to give DDM. 1H NMR spectra were used to confirm a high level of deuteration in the synthesized d39-DDM and to demonstrate its use in eliminating interfering signals from TROSY NMR spectra of a 52-kDa sugar transport protein solubilized in DDM.

  这项工作报告了均匀氘标记的n-十二烷基-β-d-麦芽糖苷（d39-DDM）的首次合成。DDM是一种温和的非离子型洗涤剂，通常用于膜蛋白的提取和纯化，以及在实验研究其结构、动力学和配体结合时的溶解。我们需要d39-DDM来溶解样品中的大型α-螺旋膜蛋白，以便进行[15N–1H]TROSY（横向弛豫优化光谱）NMR实验，从而实现最高的灵敏度和最佳的光谱分辨率。我们的d39-DDM合成使用了d7-d-葡萄糖和d25-n-十二醇，将氘标记引入麦芽糖苷和十二烷基基团中。两个葡萄糖分子，其中一个转化为具有自由C4羟基的糖苷受体，另一个转化为在C1位置被α-构型溴取代的糖苷供体，通过α(1→4)糖苷键结合在一起，形成麦芽糖，再通过用α-构型的C1溴取代将其与n-十二醇结合，得到DDM。利用1H NMR谱确认了合成的d39-DDM具有较高的氘标记水平，并展示其在消除52-kDa糖转运蛋白在DDM中溶解的TROSY NMR谱中的干扰信号方面的应用。