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2-Methoxyethoxymethyl chloride, is used as selectively cleaved under aprotic conditions in the presence of a wide range of OH-protected reagents. It is used as an OH-protecting reagent. An examples of the target molecule MEM Chloride is the side chain of roxithromycin. It is also used in the protection of the OH groups in serine and threonine during peptide synthesis. Some of the other applications include have the ability to coordinate to metals, which is thought to accelerate the cleavage by Lewis acids. The chelating ability of the MEM ether also makes it useful as a stereodirecting group in organometallic reactions, first noted in the stereo controlled addition of ?-methoxyvinyllithium to a carbonyl in the synthesis of taxusin.
JH Rigby.; JAZ Wilson. Removal of methoxyethoxymethyl ethers with trimethylsilyl chloride-sodium iodide. Tetrahedron letters. 198425(14) , 1429-1432.
RS Gross.; DS Watt. A Lewis acid-catalyzed procedure for the conversion of 2-methoxyethoxymethyl ethers to carboxylic esters. Synthetic Communications. 198717(15) , 1749-1760.
Reagent for the protection of OH groups, in the presence of a base, e.g. NaH in THF or N-Ethyldiisopropylamine, A11801. The MEM-group is more readily and cleanly introduced than methoxymethyl (MOM) and is stable to a wide range of conditions. The MEM group is selectively cleaved by mild Lewis acids, e.g. ZnBr2 or TiCl4: Tetrahedron Lett., 809, 4701, 4705 (1976); 24, 3969 (1983), PPTS: Synth. Commun., 13, 1021 (1983), in situ generated TMS iodide: Tetrahedron Lett., 25, 1429 (1984), or CeCl3: Org. Lett., 3, 1149 (2001).
For use in the protection of the OH groups in serine and threonine during peptide synthesis, see: Int. J. Pept. Prot. Res., 25, 544 (1985). See also Appendix 6.
MEM ethers have the ability to coordinate to metals, which is thought to accelerate the cleavage by Lewis acids. The chelating ability of the MEM ether also makes it useful as a stereodirecting group in organometallic reactions, first noted in the stereocontrolled addition of ɑ-methoxyvinyllithium to a carbonyl in the synthesis of taxusin: J. Am. Chem. Soc., 110, 6558 (1988), and subsequently in the addition of MeLi to an ɑß-unsaturated sulfone: J. Am. Chem. Soc., 113, 3085 (1991); see 2,2,2-Trifluoroethanol, A10788, for another example.
For cleavage by PPTS, see: Synth. Commun., 1021 (1983). For cleavage by TMS chloride/ NaI or, less effectively, by preformed TMS iodide, see: Tetrahedron Lett., 25, 1429 (1984).
Hazard Statements: H226-H302+H332-H315-H319-H335-H350
Flammable liquid and vapour. Harmful if swallowed. Harmful if inhaled. Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation. May cause cancer.
Precautionary Statements: P201-P202-P210-P233-P235-P240-P241-P242-P243-P261-P264b-P270-P271-P280i-P281-P301+P312-P303+P361+P353-P304+P340-P305+P351+P338-P308+P313-P330-P332+P313-P337+P313-P363-P370+P37
Obtain special instructions before use. Do not handle until all safety precautions have been read and understood. Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Keep container tightly closed. Keep cool. Ground/bond container and receiving equipment. Use explosion-proof electrical/ventilating/lighting/ equipment. Use only non-sparking tools. Take precautionary measures against static discharge. Avoid breathing dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Do not eat, drink or smoke when using this product. Use only outdoors or in a well-ventilated area. Wear eye/face protection. Use personal protective equipment as required. IF SWALLOWED: Call a POISON CENTER or doctor/physician if you feel unwell. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF exposed or concerned: Get medical advice/attention. Rinse mouth. If skin irritation occurs: If eye irritation persists: Wash contaminated clothing before reuse. In case of fire: