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Protection of hydroxyl- and thiol groups as 2′-0-tetrahydrofuranyl-(THF)-ethers.

✍ Scribed by C.G. Kruse; N.L.J.M. Broekhof; A. van der Gen

Publisher: Elsevier Science
Year: 1976
Tongue: French
Weight: 231 KB
Volume: 17
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)92935-6

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✦ Synopsis

An extensively used method for the protection of alcohol8 consists of their oonverslon into 2*-0-tetrahydropyrsnyl-(TIP-)ethers'.

Reaotlcn with an exoess of 2,3-dlhydro-4H-pyra3l 111 the presence of trace amounts of (p-toluenesulfonlc) acrd affords the sorresponding THP-ethers In good ylelda. This protecting group ccmblnes stablllty under a wide range of conditions wrth susceptibility to facile removal under relatively mild acxdlc oonditlcns *,3 .

4,5 Since tetrahydrofuran (THF) is known to be more basic than tetrahydropyran ) bydrolyfi1e

of tetrahydrcfuranyl-(THF-)ethers should cccur under at111 milder acidlo conditlona, uhlle the relative stablllty towards nucleophlllc reagents 1s expected to be essentially unaffected.

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