benzyl 2-deoxy-α-D-glucopyranoside | 50615-76-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl 2-deoxy-α-D-glucopyranoside
• 英文别名: benzyl 2-deoxy-α-D-arabino-hexopyranoside；(2R,3S,4R,6S)-2-(hydroxymethyl)-6-phenylmethoxyoxane-3,4-diol
• CAS: 50615-76-4
• 化学式: C₁₃H₁₈O₅
• 分子量: 254.283
• InChiKey: FLHQTQQOIIZYTL-NDBYEHHHSA-N

物化性质

• 沸点：
  448.1±45.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  79.2
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  benzyl 2-deoxy-α-D-glucopyranoside 在 palladium on activated charcoal 甲醇 、 水 、 氢气 、 sodium 、 氰化汞 、 溶剂黄146 、 zinc(II) chloride 作用下， 以 甲醇 、 乙醇 、 氯仿 为溶剂， 反应 122.0h， 生成 2-deoxy-3-O-(β-D-glucopyranosyl)-α-D-arabino-hexopyranose
  参考文献：
  名称：

  酸性条件下在羰基β位带有O-膦酰基或O-葡萄糖基取代基的2-脱氧-D-阿拉伯糖-己糖和3-脱氧-2-酮醛酸的合成及行为

  摘要：

  甲基4- ø -phosphono-和4- ø - （β- d吡喃葡萄糖基）-3-脱氧β- d -赤-2- hexulopyranosidonic酸，和3- Ó -phosphono-，和3- ö - （β -已经合成了D-吡喃葡萄糖基）-2-脱氧-α- D-阿拉伯糖-己基吡喃糖，并研究了它们在酸性介质中的行为。在100°C时，pH值为3–6时，4- O-膦酰基己基吡喃二磺酸中的无机磷酸盐的释放要比pH值为0-1时更快，并且是通过质子转移引发的消除而发生的。磷从3- O释放-膦酰基-2-脱氧-己吡喃糖通过类似的机理发生，但是慢得多。在100℃下用pH为3.4的乙酸处理导致葡萄糖从4 - O-葡糖基化的3-脱氧-己基吡喃二糖苷酸释放出来，而不是从3- O-葡糖基化的2-脱氧-己基吡喃糖中释放出来。

  DOI：

  10.1039/p19820001275
• 作为产物：
  描述：

  benzyl 2-deoxy-3,4,6-tri-O-acetyl-α-D-glucopyranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 3.0h， 生成 benzyl 2-deoxy-α-D-glucopyranoside
  参考文献：
  名称：

  A convenient synthesis of 2-deoxy-d-arabino-hexose and of its methyl and benzyl glycosides

  摘要：

  DOI：

  10.1016/s0008-6215(00)81880-7

文献信息

• Allylic strain as a stereocontrol element in the hydrogenation of 3-hydroxymethyl-cyclohex-3-en-1,2,5-triol derivatives. Synthesis of the carbasugar pseudo-2-deoxy-α-d-glucopyranose
  作者：Peng Wen、David Crich

  DOI：10.1016/j.tet.2018.04.078

  日期：2018.9

  tied up in a cyclic isopropylidene acetal with the adjacent 6-hydroxy group the cis-fused products with the ido-configuration are formed preferentially whereas protection of the hydroxymethyl group as a methoxymethyl ether results in the formation of the D-gluco isomer on hydrogenation over Raney nickel. This result is rationalized in terms of the minimization of allylic strain in the course of the reduction

  通过采用在葡萄糖系列和标准保护基操作中开发的文献方法，将2-脱氧-D-葡萄糖衍生物转化为一系列的1R，2R，5R-3-羟甲基-环己烯-1,2,5-三醇研究了将其还原为相应的非对映异构体D-葡萄糖和L-ido-2-脱氧Carbasugars的衍生物。当羟甲基与相邻的6-羟基在环状异亚丙基乙缩醛中键合时，优先形成具有偶合构型的顺式稠合产物，而羟甲基作为甲氧基甲基醚的保护导致D-的形成。阮内镍上氢化得到的葡萄糖异构体。根据还原过程中烯丙基菌株的最小化，此结果是合理的，可以制备羧甲基化糖假-2-脱氧-α-D-吡喃葡萄糖，
• Synthesis of phosphono analogues of 3-deoxy -d-arabino-hept-2-ulosonic acid 7-phosphate
  作者：Piere Le Marechal、Cléanthis Froussios、Michel Level、Robert Azerad

  DOI：10.1016/s0008-6215(00)85591-3

  日期：1981.7

  reaction of 6-bromo-6-deoxyhexoses with triethyl phosphite, followed by treatment with bromotrimethylsilane, hydrolysis with water, cyanide homologation, and chlorate-vanadate oxidation. All four, final phosphono compounds are competitive inhibitors of 3-dehydroquinate syntyhetase.

  摘要以已知的受保护的2-脱氧衍生物为原料，经六步合成3,7,8-三苯氧基-8-膦酰基-阿拉伯糖-八磺酸和7,8-脱氧-8-磷酸-D-葡萄糖基-八磺酸。 -d-阿拉伯糖-己糖和d-葡萄糖。将保护的6-醛-己二醛与亚甲基二膦酸四乙酯缩合，并通过与溴代三甲基硅烷的酯交换反应间接进行乙烯基膦酸的水解。将氰化物加到脱保护的庚糖膦酸酯中，然后将氯酸盐-钒酸盐氧化为辛磺酸衍生物。通过使6-溴-6-脱氧己糖与亚磷酸三乙酯反应，得到相应的3,7-二脱氧-7-膦酰基-阿拉伯庚酸和7-脱氧-7-膦酰基-d-葡庚糖酸，然后用溴代三甲基硅烷处理，用水水解，氰化物同化，氯酸盐-钒酸盐氧化。所有四种最终的膦酰基化合物都是3-脱氢奎宁酸合酶的竞争性抑制剂。
• Unusual stereoselectivity in sialic acid aldolase-catalyzed aldol condensations: synthesis of both enantiomers of high-carbon monosaccharides
  作者：Chun Hung Lin、Takeshi Sugai、Randall L. Halcomb、Yoshitaka Ichikawa、Chi Huey Wong

  DOI：10.1021/ja00052a008

  日期：1992.12

  An inversion of stereoselectivity in aldol condensations catalyzed by sialic acid aldolase (from Escherichia coli, Shinko American Inc.) was observed when L-mannose, 6-deoxy-L-mannose, L-talose, 2-deoxy-L-glucose, 2-deoxy-L-rhamnose, N-acetyl-L-mannosamine, D-gulose, D-arabinose, and 2-azido-2-deoxy-L-mannose were used as acceptor substrates. In all substrates tested, except the last three, a complete inversion of stereoselectivity was observed; i.e., the C-nucleophile of pyruvate attacks the re face of the acceptor carbonyl instead of the si face as in the normal case for the enantiomeric substrates. Examination of the product distribution during the course of enzymatic reactions indicates that the stereoselectivity is thermodynamically controlled in nature; i.e., attack on the re face would take place if the resulting product would be more stable than the one from the si face attack. Both enantiomers of several high-carbon monosaccharides are now accessible via the aldolase reactions. A new practical procedure has also been developed for the preparation of the aldolase products where unreacted pyruvate (usually used in 7-fold excess to drive the reaction) is decomposed with pyruvate decarboxylase to simplify product isolation.
• Enzymatic synthesis of alkyl α-2-deoxyglucosides by alkyl alcohol resistant α-glucosidase from Aspergillus niger
  作者：Young-Min Kim、Masayuki Okuyama、Haruhide Mori、Hiroyuki Nakai、Wataru Saburi、Seiya Chiba、Atsuo Kimura

  DOI：10.1016/j.tetasy.2004.11.046

  日期：2005.1

  Aspergillus niger alpha-glucosidase (ANGase) was used for an efficient syntheses of alkyl alpha-D-2-deoxyglucosides (A2DGs) and for regioselectivity studies of alkoxy-hydro additions Of D-glucal in the presence of alkyl alcohols. ANGase showed a high stability with respect to the high concentration of alkyl alcohols. The reaction conditions were optimized for pH, temperature, alkyl alcohol concentration, and D-glucal concentration. On the basis of MS and NMR analyses, A2DGs were confirmed to have only an alpha-2deoxyglucosidic bond and the two-dimensional NMR (HMBC) spectra showed to be made up of 2-deoxyglucosyl and alkyl moieties. (C) 2004 Elsevier Ltd. All rights reserved.
• WESSEL, HANS PETER, J. CARBOHYDR. CHEM., 7,(1988) N 1, 263-269
  作者：WESSEL, HANS PETER

  DOI：——

  日期：——