Top 10 similar words or synonyms for benzyloxymethyl

phenethyloxymethyl    0.802608

methylthiomethyl    0.799752

benzhydryloxymethyl    0.798407

methoxythiomethyl    0.758084

methoxymethyl    0.735839

chxo    0.723213

ethylthiomethyl    0.719039

methylthioethyl    0.709072

triphenylmethyl    0.707510

smom    0.704714

Top 30 analogous words or synonyms for benzyloxymethyl

Article Example
Holton Taxol total synthesis Protection Reagents: Benzyloxymethyl chloride, N,N-diisopropylethanamine, tetrabutylammonium iodide, in refluxing dichloromethane, 32 h.
Debromoaplysiatoxin The following step involves introducing an acidic sidechain on the C.9 hydroxyl group. This carboxylic, acidic side group is made of xylose and arabidose. The introduction is realized by protecting the C.29 and C.30 hydroxylgroups with respectively p-methoxybenzyl (MPM) and benzyloxymethyl (BOM), activating the sidechain with acid chloride, and subsequently replacing the C.30 protecting group with a more stable one, tert-butyldiphenylsilyl (TBDPS). Thereafter, the carboxylic acid can successfully attach to the backbone by esterification. In order to produce the primary alcohol, it is necessary to adjust the protecting group of the C.30 once again, back to BOM.
Holton Taxol total synthesis As shown in Scheme 3, diol 19 was protected with phosgene as a carbonate ester (20). The terminal alkene group of 20 was next converted to a methyl ester using ozonolysis followed by oxidation with potassium permanganate and esterification with diazomethane. Ring expansion to give the cyclohexane C ring 24 was achieved using a Dieckman condensation of lactone 23 with lithium diisopropylamide as a base at -78 °C. Decarboxylation of 24 required protection of the hydroxyl group as the 2-methoxy-2-propyl (MOP) ether (25). With the protecting group in place, decarboxylation was effected with potassium thiophenolate in dimethylformamide to give protected hydroxy ketone 26. In the next two steps the MOP protecting group was removed under acidic conditions, and alcohol 27 was reprotected as the more robust benzyloxymethyl ether 28. The ketone was converted to the trimethylsilyl enol ether 29, which was subsequently oxidized in a Rubottom oxidation using "m"-chloroperbezoic acid to give the trimethylsilyl protected acyloin 30. At this stage the final missing carbon atom in the Taxol ring framework was introduced in a Grignard reaction of ketone 30 using a 10-fold excess of methylmagnesium bromide to give tertiary alcohol 31. Treatment of this tertiary alcohol with the Burgess reagent (32) gave exocyclic alkene 33.