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Abstract:
Background: Ease of preparation and alkaline stability of methoxymethyl (MOM) makes it an important hydroxyl protecting group. A number of methods are available for the deprotection of MOM. Though the methods are good in general, they use solvents, require prolonged reaction time and
tedious work up. A solvent free, solid phase, fast deprotection of MOM has been developed and is the major theme of this paper.
Methods: A mixture of MOM protected compounds and pTSA is triturated in a mortar (5 min) and left at room temperature for 30 min. On addition of water (4oC),
pTSA, methanol and formaldehyde dissolved leaving the products as precipitates.
Results: A series of different MOM ethers were deprotected by this method in good to excellent yield (85-98%). The compatibility of MOM in the presence of other protections such as methoxyl, benzyl, ester,
amide, allyl and lactone was also established. Acetate protection is not stable under these conditions.
Conclusion: An efficient, selective and high yielding deprotection MOM groups by pTSA under solvent free condition is described. The process is environment friendly since no solvent
was used in the deprotection process. The reaction conditions are mild and should be useful for the deprotection of MOM derivatives of complex and labile molecules.
| Authors: | Pandurangan, Nanjan | |
| Journal: | Letters in Organic Chemistry | |
| DOI: | 10.2174/1570178614666170321103650 |
Abstract: Background: Azocalix[4] arene derivative based on 2,6-diamino pyridine has been synthesized from diazo-coupling reaction between tetradiazonium salt of calix[4]arene and 2,6-diaminopyridine, and characterized by various spectroscopic methods such as IR, 1HNMR, 13CNMR and Mass spe ... more
MSD-MAP: A Network-Based Systems Biology Platform for Predicting Disease-Metabolite Links
Abstract: Background: Cancer-associated metabolites result from cell-wide mechanisms of dysregulation. The field of metabolomics has sought to identify these aberrant metabolites as disease biomarkers, clues to understanding disease mechanisms, or even as therapeutic agents. Objective: Thi ... more
Antimalarials: Molecular Drug Targets and Mechanism of Action
Abstract: Background: Despite a reduction in the global burden of malaria, the disease remains responsible for 214 million cases and 438,000 deaths annually with 88% of the mortality occurring in sub-Saharan Africa. Malaria control largely depends on effective chemotherapy. However, the hi ... more
Synthesis of medicinally privileged heterocycles through dielectric heating
Heterocyclic compounds are enormously crucial in various industries including food, agricultural, cosmetics and pharmaceuticals. Heterocyclic pharmacophores are one of the main chemical components in drug discovery research. A report in 2013 claims that four out of six and nine out of twent ... more
A new breakthrough in the synthesis of chiral 3,6-Dihydro-2H-pyrans
The pyran ring is present in so many useful compounds, such as pharmaceuticals (antibiotics, anti-infectives, cardiovascular agents, neurological modulators, anti-allergic, anti-asthmatic, anti-inflammatory agents, reproductive and genitourinary agents, growth promoters and antidiabetic age ... more
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