beta-D-阿拉伯吡喃糖 | 6748-95-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: beta-D-阿拉伯吡喃糖
• 英文名称: β-D-arabinopyranose
• 英文别名: β-D-arabinose；D-arabinose；(2R,3S,4R,5R)-oxane-2,3,4,5-tetrol
• CAS: 6748-95-4
• 化学式: C₅H₁₀O₅
• mdl: MFCD00067708
• 分子量: 150.131
• InChiKey: SRBFZHDQGSBBOR-SQOUGZDYSA-N

物化性质

• 熔点：
  155.5°C
• 沸点：
  191.65°C (rough estimate)
• 密度：
  1.6250

计算性质

• 辛醇/水分配系数(LogP)：
  -2.5
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  90.2
• 氢给体数：
  4
• 氢受体数：
  5

安全信息

• 海关编码：
  2932999099

反应信息

• 作为反应物：
  描述：

  beta-D-阿拉伯吡喃糖 在 高氯酸 、 三溴化磷 作用下， 反应 2.08h， 生成 三-O-乙酰基-β-D-溴化阿拉伯糖
  参考文献：
  名称：

  Synthesis of 9-O-glycosyl-berberine derivatives and bioavailability evaluation

  摘要：

  To increase the bioavailability of berberine, three new 9-O-glycosyl-berberine derivatives, 9-O-glucosyl-(4a), 9-O-arabinosyl-(4b), and 9-O-erythrol-(4c) were obtained and confirmed by UV, (HNMR)-H-1, (CNMR)-C-13, and MS. The pharmacokinetic profiles of these synthetic compounds have been evaluated compared with berberine (1) and 9-O-alkyl-berberine (5) derivatives, which showed that maximum concentration (C (max)) and area under concentration-time curve (AUC) of 9-O-glycosyl-berberine increased dramatically. The results indicated that hydrophilic modification could significantly improve the bioavailability of berberine; 9-O-glycosyl-berberine might be a promising prodrug.

  DOI：

  10.1007/s00044-011-9678-1
• 作为产物：
  描述：

  [(3S,4S,5R)-2,4-dihydroxy-5-phosphonooxyoxan-3-yl] dihydrogen phosphate 生成 beta-D-阿拉伯吡喃糖
  参考文献：
  名称：

  MULLER, DANIEL;PITSCH, STEFAN;KITTAKA, ATSUSHI;WAGNER, ERNST;WINTNER, CAL+, HELV. CHIM. ACTA , 73,(1990) N, C. 1410-1468

  摘要：

  DOI：

文献信息

• Gold(III) Complexes Catalyze Deoximations/Transoximations at Neutral pH
  作者：Carles Isart、David Bastida、Jordi Burés、Jaume Vilarrasa

  DOI：10.1002/anie.201007269

  日期：2011.3.28

  Golden solution: A neutral solution of AuBr3, containing [AuBr2(OH)2]− in equilibrium with [AuBr3(OH)]− and [AuBr4]−, promotes the chemoselective hydrolysis of robust oximes into carbonyl compounds without racemization (see scheme). The food additive diacetyl acts as a NH2OH‐trapping agent, thus avoiding the formation of gold nanoparticles and allows the reaction to run catalytically.

  金色溶液：AuBr的中性溶液3，将含有[AuBr 2（OH）2 ] -处于平衡[AuBr 3（OH）] -和[AuBr 4 ] - ，促进健壮肟的化学选择性水解成无外消旋作用的羰基化合物（请参阅方案）。食品添加剂二乙酰可作为NH 2 OH捕集剂，从而避免了金纳米颗粒的形成，并使反应催化进行。
• Absolute Stereostructures of Betavulgarosides III and IV, Inhibitors of Glucose Absorption, from the Roots of Beta vulgaris L.(Sugar Beet).
  作者：Masayuki YOSHIKAWA、Toshiyuki MURAKAMI、Masahiro INADUKI、Kazuhiro HIRANO、Johji YAMAHARA、Hisashi MATSUDA

  DOI：10.1248/cpb.45.561

  日期：——

  The absolute stereostructures of betavulgarosides III and IV, which were isolated from the roots of Beta vulgaris L. (sugar beet) and exhibited inhibitory activity on glucose absorption, were determined by the chemical correlation of betavulgaroside IV with a known saponin momordin I, which included the conversion from the α-L-arabinopyranosyl moiety of momordin I to the acidic acetal-type substituent of betavulgarosides III and IV via the α-L-ribopyranosyl derivative. Furthermore, four acidic acetal-type substituent analogues were synthesized from L- and D-arabinose.

  从甜菜（Beta vulgaris L.）的根部分离得到了具有抑制葡萄糖吸收活性的β甜菜苷III和IV，并通过β甜菜苷IV与已知的皂苷momordin I的化学相关性确定了它们的绝对立体结构。这一过程包括将momordin I中的α-L-阿拉伯呋喃糖基部分转化为β甜菜苷III和IV中的酸性缩醛型取代基，即α-L-核呋喃糖衍生物。此外，还从L-和D-阿拉伯糖合成了四种酸性缩醛型取代基类似物。
• Mixed complexes of cobalt(III) with phenanthroline and galactose or arabinose
  作者：José Parada、Sergio Bunel、Exequiel Moraga、Carmen Ibarra、Nicholas D Gillitt、Clifford A Bunton

  DOI：10.1016/s0277-5387(01)00826-9

  日期：2001.7

  Abstract Mixed complexes of bis-phenanthroline cobalt(III) and α- d -galactose or β- d - or l -arabinose are identified in aqueous solution from their 1H NMR and circular dichroism (CD) spectra. Galactose forms only the Δ-complex, but d -arabinose gives preferentially Δ-, and l -arabinose preferentially Λ-complexes, consistent with structural optimization with PM3 (tm) parameters. The Λ-complex is

  摘要从1H NMR和圆二色性（CD）光谱中鉴定出双菲咯啉钴（III）与α-d-半乳糖或β-d-或1-阿拉伯糖的混合配合物。半乳糖仅形成Δ复合物，而d-阿拉伯糖优先生成Δ-和1-阿拉伯糖优先生成Λ-复合物，这与PM3（tm）参数的结构优化相一致。Λ复合物最初由β-d-阿拉伯糖形成，但Δ复合物在热力学上是优选的。吸收光谱和CD光谱的检查给出了钴（II​​I）构型的信息，并允许分配Co（III）和菲咯啉残基中的电子跃迁。
• Studies of the Pfeiffer effect induced in tris(pyridine-2,6-dicarboxylato)terbate(III) by monosaccharide aldose sugars
  作者：Harry G. Brittain

  DOI：10.1039/dt9840001367

  日期：——

  carbon 4 of the sugars (when these were present in the pyranose ring form) and the predominant [Tb(pydca)3]3– enantiomer. This suggests that an association process does indeed lead to the observed Pfeiffer effects, and that the forces leading to the formation of the outer-sphere complexes are rather specific in nature.

  在与单糖醛糖形成外球络合物后，在[Tb（pydca）3 ] 3–（pydca =吡啶-2,6-二羧酸吡啶）的外消旋混合物中诱导了光学活性，并通过圆偏振发光光谱法对其进行了研究。将D-甘油醛添加到[Tb（pydca）3 ] 3–的溶液中未观察到光学活性，这表明存在半缩醛环氧是发生外球缔合所必需的。发现诱导的光学活性的符号随所用糖的身份而变化，但是在糖的碳原子4（当它们以吡喃糖环形式存在时）的构型与主要的[Tb（ pydca）3 ] 3–对映异构体。这表明缔合过程确实导致了观察到的菲佛效应，并且导致形成外圈复合物的力在本质上是相当特殊的。
• Solvent-Dependent Mechanism and Stereochemistry of Mitsunobu Glycosylation with Unprotected Pyranoses
  作者：Hironori Takeuchi、Yusuke Fujimori、Yoshihiro Ueda、Hiromitsu Shibayama、Masaru Nagaishi、Tomoyuki Yoshimura、Takahiro Sasamori、Norihiro Tokitoh、Takumi Furuta、Takeo Kawabata

  DOI：10.1021/acs.orglett.0c01549

  日期：2020.6.19

  acidic glycosyl acceptors such as carboxylic acids, phenols, and imides, retaining its high stereoselectivity (33 examples). Glycosylation of a carboxylic acid with unprotected α-d-mannose proceeded also in an SN2 manner to directly afford a usually less accessible 1,2-cis-mannoside. One- or two-step total syntheses of five simple natural glycosides were performed using the glycosylation strategy presented

  在Mitsunobu条件下，在二恶烷中，用未保护的α- d-葡萄糖对苯甲酸高度立体选择性糖基化提出了一种S N 2机制，而在DMF中，对于非立体选择性糖基化则提出了一种S N 1机制。S N 2型立体选择性Mitsunobu糖基化通常可作为糖基供体与多种酸性糖基受体（如羧酸，酚和酰亚胺）结合使用，作为糖基供体，适用于各种未保护的吡喃糖，保持其高立体选择性（33个例子）。羧酸与未保护的α- d-甘露糖的糖基化也以S N 2方式进行，以直接提供通常较难获得的1,2-顺式-甘露糖苷。使用未保护的α- d-葡萄糖，使用此处介绍的糖基化策略进行五个简单天然糖苷的一步或两步总合成。

表征谱图