Synthesis of (R)-2-methyl-4-deoxy and (R)-2-methyl-4,5-dideoxy analogues of 6-phosphogluconate as potential inhibitors of 6-phosphogluconate dehydrogenase
Literature Information
Christophe Dardonville, Ian H. Gilbert
The synthesis of (2R)-2-methyl-4,5-dideoxy and (2R)-2-methyl-4-deoxy analogues of 6-phosphogluconate is described. The synthetic strategy relies on the Evans aldol reaction for the installation of the chiral centres in the 2- and 3-positions. The selective phosphorylation at the primary alcohol function of (2R,3S)-3,6-dihydroxy-2-methylhexanoic acid benzyl ester (5) and (2R,3S,5S)-3,5,6-trihydroxy-2-methylhexanoic acid benzyl ester (20) was achieved with dibenzyl phosphochloridate and dibenzyl phosphoiodinate respectively, working at low temperature. (2R,3S)-3-Hydroxy-2-methyl-6-phosphonoxyhexanoic acid (9) was obtained in 25% overall yield from 4-benzyloxybutanol and (2R,3S,5S)-3,5-dihydroxy-2-methyl-6-phosphonoxyhexanoic acid (28) in 10% overall yield from L-malic acid.
Related Literature
Highly active, water-compatible and easily separable magnetic mesoporous Lewis acid catalyst for the Mukaiyama–Aldol reaction in water
Fang Zhang, Xiaotao Wu, Chao Liang, Xiaoyan Li, Zhen Wang, Hexing Li
DOI: 10.1039/C4GC00178H
Transition-metal-free synthesis of vinyl sulfones via tandem cross-decarboxylative/coupling reactions of sodium sulfinates and cinnamic acids
Yanli Xu, Xiaodong Tang, Weigao Hu, Wanqing Wu, Huanfeng Jiang
DOI: 10.1039/C4GC00542B
Hydrothermal saline promoted grafting: a route to sulfonic acid SBA-15 silica with ultra-high acid site loading for biodiesel synthesis
C. Pirez, A. F. Lee, J. C. Manayil, C. M. A. Parlett, K. Wilson
DOI: 10.1039/C4GC01139B
Evaluating water miscible deep eutectic solvents (DESs) and ionic liquids as potential lubricants
Andrew P. Abbott, Robert C. Harris, Karl S. Ryder
DOI: 10.1039/C4GC00952E
Carbon-supported iron–ionic liquid: an efficient and recyclable catalyst for benzylation of 1,3-dicarbonyl compounds with alcohols
P. Moriel, A. B. García
DOI: 10.1039/C4GC00755G
A solar light-driven, eco-friendly protocol for highly enantioselective synthesis of chiral alcohols via photocatalytic/biocatalytic cascades
Sumit Choudhury, Jin-Ook Baeg, No-Joong Park, Rajesh K. Yadav
DOI: 10.1039/C4GC00885E
Synthesis of 2-substituted pyrimidines and benzoxazoles via a visible-light-driven organocatalytic aerobic oxidation: enhancement of the reaction rate and selectivity by a base
Lin Wang, Zhi-Gang Ma, Xiao-Jing Wei, Qing-Yuan Meng, Deng-Tao Yang, Shao-Fu Du, Zi-Fei Chen, Li-Zhu Wu, Qiang Liu
DOI: 10.1039/C4GC00337C
Continuous production of sugars from pyrolysis of acid-infused lignocellulosic biomass
DOI: 10.1039/C4GC00602J
Flow approaches towards sustainability
Luigi Vaccaro, Daniela Lanari, Assunta Marrocchi, Giacomo Strappaveccia
DOI: 10.1039/C4GC00410H
You might also like
How should 2-Methylbenzene-1,4-diamine dihydrochloride (CAS: 615-45-2) be stored?
2-Methylbenzene-1,4-diamine dihydrochloride (CAS: 615-45-2) should be stored in ...
Is (1S,4S)-2,5-Diazabicyclo[2.2.1]heptane dihydrobromide (CAS: 132747-20-7) safe?
(1S,4S)-2,5-Diazabicyclo[2.2.1]heptane dihydrobromide is generally considered sa...
What industries use (6-Chloropyridazin-3-YL)methanamine (CAS: 871826-15-2)?
(6-Chloropyridazin-3-YL)methanamine finds applications in the pharmaceutical ind...
What are the main uses of 2-Fluoro-3-methylphenol (CAS: 77772-72-6)?
2-Fluoro-3-methylphenol is primarily used in the synthesis of pharmaceuticals, p...
What precautions should be taken when handling 3-Methoxy-4-nitrobenzonitrile (CAS: 177476-75-4)?
When handling 3-Methoxy-4-nitrobenzonitrile, it is important to wear appropriate...
What precautions should be taken when handling 1,3-Oxazolo[4,5-b]pyridine-2(3H)-thione (CAS: 211949-57-4)?
When handling 1,3-Oxazolo[4,5-b]pyridine-2(3H)-thione (CAS: 211949-57-4), it is ...
What regulatory guidelines apply to 4-Ethynylbenzamide (CAS: 90347-86-7)?
4-Ethynylbenzamide (CAS: 90347-86-7) falls under various regulatory guidelines i...
What are the main uses of 3-(2-Ethylphenyl)-2-thioxo-4-imidazolidinone (CAS: 186822-57-1)?
3-(2-Ethylphenyl)-2-thioxo-4-imidazolidinone is primarily used as an intermediat...
What is (2-Fluoro-6-methoxyphenyl)acetic acid (CAS: 500912-19-6)?
(2-Fluoro-6-methoxyphenyl)acetic acid, also known as 4-fluoro-3-methoxybenzoic a...
What is the market or research trend for 2-[4-(Hydroxymethyl)phenoxy]ethanol (CAS: 102196-18-9)?
Market trends for 2-[4-(Hydroxymethyl)phenoxy]ethanol (CAS: 102196-18-9) indicat...
Source Journal
Organic & Biomolecular Chemistry

Organic & Biomolecular Chemistry (OBC) publishes original and high impact research and reviews in organic chemistry. We welcome research that shows new or significantly improved protocols or methodologies in total synthesis, synthetic methodology or physical and theoretical organic chemistry as well as research that shows a significant advance in the organic chemistry or molecular design aspects of chemical biology, catalysis, supramolecular and macromolecular chemistry, theoretical chemistry, mechanism-oriented physical organic chemistry, medicinal chemistry or natural products. Articles published in the journal should report new work which makes a highly-significant impact in the field. Routine and incremental work is generally not suitable for publication in the journal. More details about key areas of our scope are below. In all cases authors should include in their article clear rationale for why their research has been carried out.










![5-Bromo-3-isopropyl-1H-pyrrolo[2,3-b]pyridine structure 5-Bromo-3-isopropyl-1H-pyrrolo[2,3-b]pyridine structure](https://static.chemtradehub.com/structs/125/1256819-54-1-8620.webp)
![[1-(5-Methyl-2-pyridinyl)-1H-pyrazol-4-yl]methanol structure [1-(5-Methyl-2-pyridinyl)-1H-pyrazol-4-yl]methanol structure](https://static.chemtradehub.com/structs/143/1439822-99-7-6cc9.webp)


