α-D-xylopyranose tetraacetate | 1233-03-0

• 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: α-D-xylopyranose tetraacetate
• 英文别名: tetra-O-acetyl-α-D-xylose；1,2,3,4-tetra-O-acetyl-α-D-xylopyranose；1,2,3,4-tetra-O-acetyl-D-xylopyranoside；1,2,3,5-tetra-O-acetate-D-xylopyranose；tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate；Tetra-O-acetyl-α-D-xylopyranose；1,2,3,4-tetra-O-acetyl-D-xylopyranose；tetra-O-acetyl-α-D-xyloside；α-D-xylose tetraacetate；D-xylose tetraaacetate；1,2,3,4-Tetra-O-acetyl-alpha-D-xylopyranose；[(3R,4S,5R,6R)-4,5,6-triacetyloxyoxan-3-yl] acetate
• CAS: 1233-03-0
• 化学式: C₁₃H₁₈O₉
• 分子量: 318.281
• InChiKey: MJOQJPYNENPSSS-YVECIDJPSA-N

物化性质

• 熔点：
  57-59 °C
• 沸点：
  362.9±42.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  114
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  α-D-xylopyranose tetraacetate 生成 tetra-O-acetyl-β-D-xylopyranose
  参考文献：
  名称：

  The Acid-catalyzed Anomerization of Acetylated Aldopyranoses¹

  摘要：

  DOI：

  10.1021/ja01515a041
• 作为产物：
  描述：

  tetra-O-acetyl-β-D-xylopyranose 生成 α-D-xylopyranose tetraacetate
  参考文献：
  名称：

  The Acid-catalyzed Anomerization of Acetylated Aldopyranoses¹

  摘要：

  DOI：

  10.1021/ja01515a041

文献信息

• Stereoselective acetylation of hemicellulosic C5-sugars
  作者：Zachary D. Herde、Prathap D. John、Dania Alvarez-Fonseca、Jagannadh Satyavolu、Christopher T. Burns

  DOI：10.1016/j.carres.2017.03.008

  日期：2017.4

  dimethylaminopyridine (DMAP) is described. The peracetylated d-xylose and l-arabinose alpha pyranose anomers 2α and 5α are obtained in 97% and 56% yields respectively. The peracetylated d-xylose beta pyranose anomer 2β is obtained in 71% yield through simple modification of the reaction conditions. Details regarding synthesis and isolation optimization studies under different conditions are presented below

  描述了在存在或不存在催化量的二甲基氨基吡啶（DMAP）的情况下使用三乙胺和乙酸酐的组合对α-d-木糖（1）和α-1-阿拉伯糖（4）进行立体选择性过乙酰化。过乙酰化的d-木糖和1-阿拉伯糖α吡喃糖异构体2α和5α分别以97％和56％的产率获得。通过简单地改变反应条件，以71％的产率获得了全乙酰化的d-木糖β吡喃糖异构体2β。下面介绍了有关在不同条件下进行合成和分离优化研究的详细信息。本文公开的立体选择性过乙酰化反应已被用于分离d-木糖和1-阿拉伯糖的混合物，作为它们的过乙酰化衍生物2β和5α，产率为47％和42％，并且可以在脱乙酰基之后提供纯戊糖。
• An efficient chemical-enzymatic synthesis of 4-nitrophenyl β-xylobioside: a chromogenic substrate for xylanases
  作者：Adva Mechaly、Valery Belakhov、Yuval Shoham、Timor Baasov

  DOI：10.1016/s0008-6215(97)00209-7

  日期：1997.11

  Abstract 4-Nitrophenyl-β-xylobioside was synthesized by an improved short chemical-enzymatic method, based on the use of xylobiose as a starting material. Xylobiose was prepared following extensive enzymatic digestion of birchwood xylan with xylanase T-6. The resulting digest, containing mainly xylobiose and xylose, was directly subjected to an acetylation step, which after silica gel chromatography

  摘要以木糖为原料，采用改进的短化学酶法合成了4-硝基苯基-β-木糖苷。在用木聚糖酶T-6对桦木木聚糖进行广泛的酶消化之后，制备木糖。将所得的主要包含木糖和木糖的消化物直接进行乙酰化步骤，该步骤在硅胶色谱法后提供高纯度的木糖六乙酸盐。用乙酸中的HBr溴化可定量获得相应的溴化物，在偶联和脱保护步骤后，可得到目标物4-硝基苯基-β-木二糖苷。
• The influence of boric acid on the acetylation of aldoses: ‘one-pot’ syntheses of penta-O-acetyl-β-D-glucofuranose and its crystalline propanoyl analogue
  作者：Richard H. Furneaux、Phillip M. Rendle、Ian M. Sims

  DOI：10.1039/b002841j

  日期：——

  When glucose and boric acid are heated in acetic acid a soluble compound forms from which, with acetic anhydride and catalytic amounts of sulfuric acid, a mixture consisting of >90% of the glucofuranose per-acetates (α∶β ratio 1∶1.8) is obtained in high yield. In the absence of the sulfuric acid partial acetylation takes place and penta-O-acetyl-β-D-glucofuranose (α∶β ratio 1∶52) is obtainable in good yield by removal of boric acid and completion of the esterification by addition of acetic anhydride and pyridine. A new, crystalline glucofuranose, penta-O-propanoyl-β-D-glucofuranose, is obtained in 58% yield in a ‘one-pot’ procedure using boric acid. The effects of boric acid on the acid-catalysed acetylation of other aldo-hexoses and -pentoses suggest that the synthesis of furanosyl per-esters could be successful with xylose and idose as well as with glucose. p

  当葡萄糖和硼酸在醋酸中加热时，会形成一种可溶性化合物，从中通过醋酐和少量的硫酸催化，可以获得含有>90%的葡萄呋喃糖全乙酸酯（α∶β比率为1∶1.8）的高产率混合物。在没有硫酸的情况下，会发生部分乙酰化，通过去除硼酸并加入醋酐和吡啶完成酯化反应，可以以良好的产率获得五-O-乙酰基-β-D-葡萄呋喃糖（α∶β比率为1∶52）。通过使用硼酸的“一锅法”程序，可以以58%的产率获得一种新的结晶葡萄呋喃糖，即五-O-丙酸酰基-β-D-葡萄呋喃糖。 硼酸对其他己醛糖和戊醛糖的酸催化乙酰化反应的影响表明，与葡萄糖一样，木糖和艾杜糖的呋喃糖全酯合成也可能是成功的。
• Serine and Threonine Schiff Base Esters React with β-Anomeric Peracetates in the Presence of BF₃·Et₂O to Produce β-Glycosides
  作者：Charles M. Keyari、Robin Polt

  DOI：10.1080/07328303.2010.508295

  日期：2010.5

  and more efficient alternatives to published methods. L-serine or L-threonine benzyl ester hydrochloride salts were reacted with the diarylketimine bis-(4-methoxyphenyl)-methanimine in CH3CN at rt to form the more nucleophilic Schiff bases 3a and 3b in excellent yield. These Schiff bases exhibited ring-chain tautomerism in CDCl3 as shown by 1H NMR. Schiff bases 3a and 3b, acting as glycosyl acceptors

  据报道，利用活化的席夫碱糖基受体对L-丝氨酸和L-苏氨酸的糖基化进行了改进的方法，这是已公开方法的较便宜且更有效的替代方法。使L-丝氨酸或L-苏氨酸苄基酯盐酸盐与CH 3 CN中的二芳基酮亚胺双-（4-甲氧基苯基）-甲亚胺在室温下反应，以优异的产率形成更具亲核性的席夫碱3a和3b。如1 H NMR所示，这些席夫碱在CDCl3中表现出环链互变异构现象。希夫碱3a和3b充当糖基受体，在室温下与简单的过乙酸乙酸供体反应，并以BF3·OEt2促进，以优异的收率和纯度提供相应的L-丝氨酸和L-苏氨酸O-连接的糖苷。二肽酯Schiff碱Ar2C = N-Ser-Val-OCH3 3e也反应生成β-糖苷，收率极高，且没有差向异构化。用微波辐射，反应在2至5分钟内完成。为了进一步研究该反应，研究了经典的AgOTf促进的D-吡喃葡萄糖基，乳糖基和麦芽糖基溴化物的Koenigs-Knorr反应，提供了35％至
• Cu(ClO₄)₂·6H₂O catalyzed solvent free per-O-acetylation and sequential one-pot conversions of sugars to thioglycosides
  作者：Debnath Chatterjee、Abhijit Paul、Rajkamal Rajkamal、Somnath Yadav

  DOI：10.1039/c5ra03461b

  日期：——

  The solvent free per-O-acetylation of various reducing and non-reducing sugars has been carried out using stoichiometric amounts of acetic anhydride and copper(ii) perchlorate hexahydrate as the catalyst.

  各种还原糖和非还原糖的无溶剂O-乙酰化反应已经使用等物质量的乙酸酐和六水合氯酸铜(ii)作为催化剂进行。