High yield protection of alcohols, including tertiary and base sensitive alcohols, as benzhydryl ethers by heating with diphenyldiazomethane in the absence of any other reagent

Synthesis of the enantiomers of XYLNAc and LYXNAc: comparison of β-N-acetylhexosaminidase inhibition by the 8 stereoisomers of 2-N-acetylamino-1,2,4-trideoxy-1,4-iminopentitols

“…52,53 Protection of base-sensitive alcohols under neutral conditions by heating with diphenyldiazomethane gave the corresponding benzhydryl ethers in high yields. 54 Reaction of 36L with diphenyldiazomethane in toluene gave the benzhydryl protected lactone 41L (75%). Reduction of 41L by initial treatment with DIBAL at −78 °C followed by sodium borohydride at rt gave the diol 42L (88%) which on esterification with methanesulfonyl chloride in the presence of pyridine afforded the dimesylate 43L in quantitative yield.…”

Total Synthesis and Glycosidase Inhibition of Broussonetine I and J2

“…Many attempts of trying to protect the free hydroxyl group of lactone 20 failed to give decent results, such as protecting with TBS, MOM, etc. Finally, it was found that diphenylmethyl works well as protecting group for lactone 20 . The protected lactone 21 was then treated with lithium aluminum hydride and methanesulfonyl chloride successively, followed by nucleophilic substitution of allylamine, to give N -allyl piperidine 13 in excellent overall yields.…”

Looking glass inhibitors: both enantiomeric N-benzyl derivatives of 1,4-dideoxy-1,4-imino-d-lyxitol [a potent competitive inhibitor of α-d-galactosidase] and of 1,4-dideoxy-1,4-imino-l-lyxitol [a weak competitive inhibitor of α-d-galactosidase] inhibit naringinase, an α-l-rhamnosidase competitively

“…Protection of carbohydrate alcohols as the corresponding benzhydryl ethers by reaction with diazomethane, 20 a procedure that does not require any acid or base catalyst, is particularly suitable for lactones with an acidic proton at C2. 21 The present six-step syntheses of LIL 1L and DIL 1D from the readily available acetonides of For the synthesis of LIL 1L, the acetonide of D-ribonolactone 3D was heated at reflux with diphenyldiazomethane in acetonitrile to give the benzhydryl ether 10D in 82% yield (Scheme 3). The reduction of the fully protected lactone 10D with sodium borohydride in methanol afforded the diol 11D (81% yield), which was esterified with mesyl chloride in pyridine to form the dimesylate 12D in 93% yield.…”