1,2-O-(methylethylidene)-3-O-(phenylmethyl)-α-D-ribofuranuroic acid | 120417-90-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1,2-O-(methylethylidene)-3-O-(phenylmethyl)-α-D-ribofuranuroic acid
• 英文别名: 1,2-O-Isopropylidene-3-O-benzyl-α-D-ribo-furanuronic acid；(3aR,5S,6S,6aR)-2,2-dimethyl-6-phenylmethoxy-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole-5-carboxylic acid
• CAS: 120417-90-5
• 化学式: C₁₅H₁₈O₆
• 分子量: 294.304
• InChiKey: SENRNXPZVZAZLH-GFQSEFKGSA-N

物化性质

• 熔点：
  115-118 °C
• 沸点：
  435.1±45.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1,2-O-(methylethylidene)-3-O-(phenylmethyl)-α-D-ribofuranuroic acid 在 草酰氯 、 N,N-二甲基甲酰胺 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 1,2-O-Isopropylidene-3-O-benzyl-6-deoxy-6-diazo-α-D-ribo-hexo-furan-5-ulose
  参考文献：
  名称：

  Synthesis of C1-C6 Segment of Carbonolide B: Wolff Rearrangement of Sugar α-Diazo Ketones

  摘要：

  银苯甲酸盐催化的Wolff重排反应在甲醇中对一系列由呋喃糖酸衍生的α-重氮酮进行，获得了良好的产率，生成了相应的一个碳同源物——甲基-5-脱氧-己糖呋喃酸酯。甲基-1,2-O-异丙烯基-3-O-甲基-5-脱氧-α-d-木糖-己糖呋喃酸酯在合成碳醇 B（16个成员的大环抗生素碳霉素 B的苷元）的右侧翼段中的应用得到了验证。

  DOI：

  10.1055/s-2000-6343
• 作为产物：
  描述：

  3-O-benzyl-1,2-O-isopropylidene-α-D-ribo-pentodialdo-1,4-furanose 在 sodium chlorite 、 sodium dihydrogenphosphate 、 双氧水 作用下， 以 水 、 乙腈 为溶剂， 以88%的产率得到1,2-O-(methylethylidene)-3-O-(phenylmethyl)-α-D-ribofuranuroic acid
  参考文献：
  名称：

  差异保护的酒石醛的新型合成等同物。一个简单的途径来获得有用的c-4手性合成子。

  摘要：

  据报道由D-葡萄糖合成4-乙酰氧基-3-O-苄基-1,2-O-异亚丙基醛糖苷酶。这些酒石醛的合成当量在乙酰氧基化中心被化学选择性还原，从而产生了一系列有用的差异保护的C-4手性合成子。

  DOI：

  10.1016/s0040-4039(00)82295-9

文献信息

• Diastereoselective syntheses of 1-deoxyhomonojirimycin and two new 1,5,6-trideoxy-1,5-iminoheptitols with d-allo- and l-talo-configuration
  作者：Géraldine Le Bouc、Christine Thomassigny、Christine Greck

  DOI：10.1016/j.tetasy.2006.07.022

  日期：2006.8

  The synthesis of 1-deoxyhomonojirimycin 2, as well as two new diastereomers, namely 1,5,6-trideoxy-1,5-imino-D-allo-heptitol 3 and 1,5,6-trideoxy-1,5-imino-L-talo-heptitol 4, is described. Compound 2 was obtained from 1,2:5,6-di-O-isopropylidene-alpha-D-glucofuranose-while 3 and 4 were obtained from 1, 2:5,6-di-O-isopropylidene-alpha-D-allofuranose. These compounds were transformed in a few steps to the corresponding beta-ketoesters 12 and 18, respectively, which were hydrogenated diastereoselectively in the presence of chiral ruthenium complexes with total control of the C-5 stereogenic centre. The resulting beta-hydroxyesters 13, 19a and 19b are key intermediates for the syntheses of the 1,5,6-trideoxy-1,5-iminoheptitols 2, 3 and 4, respectively. (c) 2006 Elsevier Ltd. All rights reserved.
• New chirons from D-glucose. Regio- and diastereoselective carbon-carbon bond-forming reactions exploiting novel aldotetrofuranose acetates as chiral synthetic equivalents of tartaric aldehydes
  作者：Dilip D. Dhavale、Emilio Tagliavini、Claudio Trombini、Achille Umani-Ronchi

  DOI：10.1021/jo00278a022

  日期：1989.8
• Towards stable di-carba analogues of guanofosfocins
  作者：Jan Duchek、Mu-Hua Huang、Andrea Vasella

  DOI：10.1016/j.tetlet.2011.02.102

  日期：2011.6

  Guanofosfocins are strong inhibitors of chitin synthases, but also very prone to hydrolytic cleavage. Two advanced intermediates 15 and 20 for the synthesis of stable di-carba-guanofosfocins were prepared via ester 11. Acylation of the allylic C-glycoside 6 with riburonic acid chloride 10 afforded ester 11 in 79% yield. This ester was converted to 15 in four steps and in 54% yield and to 20 in eight steps and in 20% yield. (C) 2011 Elsevier Ltd. All rights reserved.
• DHAVALE, DILIP D.;TAGLIAVINI, EMILIO;TROMBINI, CLAUDIO;UMANI-RONCHI, ACHI+, J. ORG. CHEM., 54,(1989) N7, C. 4100-4105
  作者：DHAVALE, DILIP D.、TAGLIAVINI, EMILIO、TROMBINI, CLAUDIO、UMANI-RONCHI, ACHI+

  DOI：——

  日期：——
• DHAVALE, DILIP D.;TAGLIAVINI, EMILIO;TROMBINI, CLAUDIO;UMANI-RONCHI, ACHI+, TETRAHEDRON LETT., 29,(1988) N 47, C. 6163-6166
  作者：DHAVALE, DILIP D.、TAGLIAVINI, EMILIO、TROMBINI, CLAUDIO、UMANI-RONCHI, ACHI+

  DOI：——

  日期：——