benzyl 3,4-O-isopropylidene-β-L-erythro-pentopyranosid-2-ulose | 65247-32-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧吡喃
• 英文名称: benzyl 3,4-O-isopropylidene-β-L-erythro-pentopyranosid-2-ulose
• 英文别名: (3aS,6S,7aS)-2,2-dimethyl-6-phenylmethoxy-4,7a-dihydro-3aH-[1,3]dioxolo[4,5-c]pyran-7-one
• CAS: 65247-32-7
• 化学式: C₁₅H₁₈O₅
• 分子量: 278.305
• InChiKey: XMUSRGALEPIMPU-UBHSHLNASA-N

物化性质

• 熔点：
  45-47 °C
• 沸点：
  145 °C(Press: 0.25 Torr)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  benzyl 3,4-O-isopropylidene-β-L-erythro-pentopyranosid-2-ulose 在 sodium tetrahydroborate 、 三氟乙酸 作用下， 以 甲醇 为溶剂， 反应 5.0h， 生成 L-ribose
  参考文献：
  名称：

  A Practical Synthesis of L-FMAU from L-Arabinose

  摘要：

  A practical synthesis of 2'-deoxy-2'-fluoro-5-methyl-beta-L-arabinofuranosyl uracil (14, L-FMAU) was developed from L-arabinose. L-Arabinose was converted to L-ribose 5, which was used for the synthesis of bromosugar 12 via 2,3,5-O-tribenzoyl-1-O-acetyl-beta-L-ribofuranose 8, which was subjected to condensation with silylated thymine and the resulting protected L-FMAU 13 was deprotected to afford L-FMAU in 14 steps in 8 % overall yield.

  DOI：

  10.1080/15257779908043066
• 作为产物：
  描述：

  L-(+)-arabinose 在 重铬酸吡啶 、 4 A molecular sieve 、 对甲苯磺酸 、 溶剂黄146 、 乙酰氯 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 136.0h， 生成 benzyl 3,4-O-isopropylidene-β-L-erythro-pentopyranosid-2-ulose
  参考文献：
  名称：

  阿拉伯糖衍生的果糖对烯烃的催化不对称环氧化

  摘要：

  四个1-赤-2- uloses从L-阿拉伯糖通过涉及费歇尔糖苷化，缩醛化和氧化的反应序列中容易地制备。在异头异构中心的庞大空间传感器可以增强二环氧乙烷环氧化的立体选择性，并且其中一种对高二苯乙烯的对映体选择性（最高90％ee）。然而，在碱性条件下，环氧化过程中催化剂分解，最大化学收率仅为13％。三1-苏-3-果糖可以克服酯基团α对酮官能团的吸电子作用而产生的分解问题。使用带有两个侧酯基的酮，最佳化学收率可达93％。一种改进的果糖对反式二取代和三取代的烯烃表现出中等的对映选择性（40-68％ee）。

  DOI：

  10.1016/s0040-4020(03)00145-5

文献信息

• A solid-phase approach to novel purine and nucleoside analogs
  作者：Junbiao Chang、Chunhong Dong、Xiaohe Guo、Weidong Hu、Senxiang Cheng、Qiang Wang、Rongfeng Chen

  DOI：10.1016/j.bmc.2005.05.007

  日期：2005.8

  This paper describes a method for the preparation of purine analogs using the solid-phase approach. Nucleoside bases were constructed on Merrifield resin by sequential displacement of purine dichloride with amines, and after detachment, the purine analogs were condensed with d,l-ribofuranoside compounds by the Vorbruggen method. Thereof, l-ribofuranoside was prepared from l-arabinose via the selective

  本文介绍了一种使用固相方法制备嘌呤类似物的方法。通过用胺依次置换二氯化嘌呤，在Merrifield树脂上构建核苷碱基，分离后，通过Vorbruggen方法将嘌呤类似物与d，l-核呋喃糖苷化合物缩合。其中，通过2-OH基团的选择性氧化还原程序，由1-阿拉伯糖制备1-核呋喃糖苷。一些化合物对PBM细胞中的HIV-1表现出中等活性。
• Efficient synthesis of 2-deoxy-l-erythro-pentose (2-deoxy-l-ribose) from l-arabinose
  作者：Youhoon Chong、Chung K Chu

  DOI：10.1016/s0008-6215(01)00329-9

  日期：2002.3

  2-deoxy-L-erythro-pentose (2-deoxy-L-ribose) starting from L-arabinose was developed using Barton-type free-radical deoxygenation reaction as a key step. The radical precursor, a phenoxythiocarbonyl ester, was prepared in situ, and the most efficient deoxygenation was achieved by slow addition of tributyltin hydride to the reaction mixture.

  以Barton型自由基脱氧反应为关键步骤，开发了一种从L-阿拉伯糖开始大规模合成2-deoxy-L-赤-戊糖（2-deoxy-L-核糖）的有效实用途径。 。原位制备自由基前体苯氧基硫代羰基酯，并通过向反应混合物中缓慢添加氢化三丁基锡来实现最有效的脱氧。
• Synthesis of homochiral 2-<i>C</i>-trifluoromethyl D-and L-ribose<i>via</i>trifluoromethylation of pentopyranosid-2-uloses
  作者：Uwe Eilitz、Christoph Böttcher、Lothar Hennig、Klaus Burger、Alois Haas、Simone Gockel、Joachim Sieler

  DOI：10.1002/jhet.5570400221

  日期：2003.3

  Efficient syntheses of 2-C-trifluoromethyl D- and L-ribose and some O-glycosides via trifluoromethylation of D- and L-3,4-O-isopropylidene-β-erythro-pentopyranosid-2-ulose with Ruppert's reagent are described.

  描述了用Ruppert's试剂通过D-和L-3,4- O-异亚丙基-β-赤型-戊吡喃二糖-2-ul的三氟甲基化来有效合成2- C-三氟甲基D-和L-核糖以及一些O-糖苷。
• A bioisosteric oligosaccharide mimetic based on isofagomine-type monomers
  作者：Xifu Liang、Bent O. Petersen、Jens Ø. Duus、Mikael Bols

  DOI：10.1039/b103756k

  日期：2001.11.1

  A series of hydroxylated piperidine oligomers that resemble oligosaccharides is synthesised. Prepared were 5, a mimic of 3-O-L-fucopyranosyl-D-galactopyranose, 6, a mimic of 3-O-D-galactopyranosyl-D-galactopyranose and 7, a mimic of 3-O-3-O-[3-O-(L-fucopyranosyl)-D-galactopyranosyl]-D-galactopyranosyl}-D-galactopyranose. Conformational analysis of the new compounds using NMR spectroscopy showed them to have predominant conformations that were similar to those adopted by β-O-glycosides. The inhibition of a series of glycosidases by 5–7 was investigated and found to be inferior to that of the corresponding unsubstituted isofagomines.

  合成了一系列类似于寡糖的羟基化哌啶低聚物。制备了5个，3-O-L-吡喃岩藻糖基-D-吡喃半乳糖的模拟物，6个，3-O-D-吡喃半乳糖基-D-吡喃半乳糖的模拟物和7个，3-O-D-吡喃半乳糖基-D-吡喃半乳糖的模拟物3-O-3-O-[3-O-(L-吡喃岩藻糖基)-D-吡喃半乳糖基]-D-吡喃半乳糖基}-D-吡喃半乳糖。使用核磁共振波谱对新化合物进行构象分析表明，它们具有与 β-O-糖苷相似的主要构象。对 5-7 一系列糖苷酶的抑制作用进行了研究，发现其效果不如相应的未取代的异法戈明。
• Synthesis of 6- and 7-(1,2,3-Trihydroxy-1,2-O-isopropylidenepropyl)pteridines and Deoxygenation of Their 3’-Hydroxy Groups
  作者：Tadashi Hanaya、Daisuke Takayama、Hiroshi Yamamoto

  DOI：10.3987/com-06-s(w)33

  日期：——

  Treatment of 3,4-O-isopropylidene-L-threo-pentos-2-ulose (7) with 5,6-diamino-1,3-dimethyluracil (8) afforded 1,3-dimethyl-6-[(1R,2S)-1,2,3-trihydroxy-1,2-O-isopropylidenepropyl]lumazine (9a) and its 7-substituted isomer (9b). Deoxygenation of 3'-hydroxy groups of 9a,b was investigated in connection with a practical transformation of neopterin into biopterin.