3-Deoxy-1,2:5,6-di-O-isopropylidene-3-C-methyl-α-D-allofuranose | 26293-58-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-Deoxy-1,2:5,6-di-O-isopropylidene-3-C-methyl-α-D-allofuranose
• 英文别名: (3aR,5S,6R,6aR)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2,6-trimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole
• CAS: 26293-58-3
• 化学式: C₁₃H₂₂O₅
• 分子量: 258.315
• InChiKey: JJERHWIKEOHNLR-KAMPLNKDSA-N

物化性质

• 沸点：
  301.2±42.0 °C(Predicted)
• 密度：
  1.088±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-Deoxy-1,2:5,6-di-O-isopropylidene-3-C-methyl-α-D-allofuranose 在 吡啶 、 lithium aluminium tetrahydride 、 硫酸 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 28.0h， 生成 3,6-dideoxy-1,2-O-isopropylidene-3-C-methyl-α-D-allofuranose
  参考文献：
  名称：

  Lichtenthaler, Frieder W.; Dinges, Juergen; Fukuda, Yoshimasa, Angewandte Chemie, 1991, vol. 103, # 10, p. 1385 - 1389

  摘要：

  DOI：
• 作为产物：
  描述：

  ((3aR,5S,6R,6aR)-tetrahydro-2,2-dimethyl-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)furo[2,3-d][1,3]dioxol-6-yl)methanol 在 palladium on activated charcoal N-溴代丁二酰亚胺(NBS) 、 氢气 、 sodium acetate 、 三苯基膦 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 25.0~50.0 ℃ 、206.84 kPa 条件下， 反应 16.0h， 生成 3-Deoxy-1,2:5,6-di-O-isopropylidene-3-C-methyl-α-D-allofuranose
  参考文献：
  名称：

  Reaction of carbohydrate halides with magnesium. Novel carbon-carbon coupling of sugar derivatives via organometallic intermediates

  摘要：

  DOI：

  10.1021/jo00338a029

文献信息

• Synthesis and Structure–Activity Relationship Studies of C2-Modified Analogs of the Antimycobacterial Natural Product Pyridomycin
  作者：Maryline Kienle、Patrick Eisenring、Barbara Stoessel、Oliver P. Horlacher、Samuel Hasler、Gwénaëlle van Colen、Ruben C. Hartkoorn、Anthony Vocat、Stewart T. Cole、Karl-Heinz Altmann

  DOI：10.1021/acs.jmedchem.9b01457

  日期：2020.2.13

  A series of derivatives of the antimycobacterial natural product pyridomycin have been prepared with the C2 side chain attached to the macrocyclic core structure by a C-C single bond, in place of the synthetically more demanding enol ester double bond found in the natural product. Hydrophobic C2 substituents of sufficient size generally provide for potent anti-Mtb activity of these dihydropyridomycins

  已经制备了一系列抗分枝杆菌天然产物吡咯霉素的衍生物，其中C2侧链通过CC单键连接到大环核心结构上，代替了天然产物中合成上要求更高的烯醇酯双键。足够大小的疏水性C2取代基通常为这些二氢吡啶霉素提供强大的抗Mtb活性（最小抑制浓度（MIC）约为2.5μM），因此一些类似物接近天然吡咯霉素的活性。令人惊奇地，与吡啶霉素相反，这些化合物中的一些对结核分枝杆菌（Mtb）中InhA的过表达不敏感。
• Phosphomolybdic Acid Supported on Silica Gel: An Efficient, Mild and Reusable Catalyst for the Chemoselective Hydrolysis of Acetonides
  作者：J. S. Yadav、S. Raghavendra、M. Satyanarayana、E. Balanarsaiah

  DOI：10.1055/s-2005-872701

  日期：——

  Carbohydrate acetonides were chemoselectively cleaved to the corresponding diols by using environmentally benign phosphomolybdic acid (H3PMo12O40) supported on silica gel (PMA-SiO2) at ambient temperature in a short span of 5-7 minutes in acetonitrile. Acid-labile protective groups such as THP, TBS, TBDPS, MOM, OMe and PMB were found to be stable under the reaction conditions.

  碳水化合物乙缩醛在环境友好的负载型磷钼酸（H3PMa href=https://www.molaid.com/MS_187332 target="_blank">MO12O40/硅胶，简称PMA-SiO2）作用下，于室温、乙腈溶液中仅需5至7分钟即可选择性地裂解为相应的二醇。在这种反应条件下，如THP、TBS、TBDPS、MOM、OMe和PMB等对酸不稳定的保护基团均能保持稳定。
• Chemoselective hydrolysis of terminal isopropylidene acetals in acetonitrile using molecular iodine as a mild and efficient catalyst
  作者：J.S. Yadav、M. Satyanarayana、S. Raghavendra、E. Balanarsaiah

  DOI：10.1016/j.tetlet.2005.10.043

  日期：2005.12

  A simple, mild and efficient method for deprotection of acetonides in the presence of molecular iodine is described. Acid labile protecting groups such as PMB, OMe, OBn, allyl and propargyl are compatible with the reaction conditions, while TBS, TBDPS, TMS and THP ethers were unstable under the same conditions.

  描述了一种在分子碘存在下使丙酮化物脱保护的简单，温和和有效的方法。酸不稳定的保护基（如PMB，OMe，OBn，烯丙基和炔丙基）与反应条件兼容，而TBS，TBDPS，TMS和THP醚在相同条件下不稳定。
• Carbohydrate-based approach to four enantiomerically pure 2-naphthylmethyl 3-hydroxy-2-methylbutanoates
  作者：Bogdan Doboszewski、Piet Herdewijn

  DOI：10.1016/j.tetlet.2007.12.104

  日期：2008.2

  Chiral pool approach using d-glucose, l-xylose, and d- and l-arabinoses was used to obtain four stereoisomeric 3-hydroxy-2-methylbutanoic acids with well defined configurations. The acids were isolated as fluorescent 2-naphthylmethyl esters after reaction with 2-naphthyldiazomethane.

  使用d-葡萄糖，l-木糖以及d-和l-阿拉伯糖的手性库法获得了具有明确定义构型的四种立体异构体3-羟基-2-甲基丁酸。与2-萘基重氮甲烷反应后，分离出作为荧光的2-萘基甲基酯的酸。
• Radical-chain deoxygenation of tertiary alcohols, protected as their methoxymethyl (MOM) ethers, using thiols as polarity-reversal catalysts
  作者：Hai-Shan Dang、Paola Franchi、Brian P. Roberts

  DOI：10.1039/b000533i

  日期：——

  The deoxygenation of tertiary alcohols can be accomplished by heating their MOM ethers in the presence of a peroxide initiator and a thiol catalyst: the proposed radical-chain mechanism is supported by EPR spectroscopic studies.

  叔醇的脱氧可以通过在过氧化物引发剂和硫醇催化剂存在下加热它们的 MOM 醚来完成：EPR 光谱研究支持了所提出的自由基链机制。