Chemoenzymatic convergent synthesis of 2'-O,4'-C-Methyleneribonucleosides

TY - JOUR

T1 - Chemoenzymatic convergent synthesis of 2'-O,4'-C-Methyleneribonucleosides

AU - Sharma, Vivek K.

AU - Kumar, Manish

AU - Olsen, Carl Erik

AU - Prasad, Ashok K.

PY - 2014/7/3

Y1 - 2014/7/3

N2 - Novozyme-435-catalyzed efficient regioselective acetylation of one of the two diastereotopic hydroxymethyl functions in 3-O-benzyl-4-C-hydroxymethyl-1,2- O-isopropylidene-α-d-ribofuranose has been achieved. The enzymatic methodology has been successfully utilized for convergent synthesis of bicyclic nucleosides (LNA monomers) T, U, A, and C. Further, it has been demonstrated that Novozyme-435 can be used for 10 cycles of the acylation reaction without losing selectivity and efficiency.

AB - Novozyme-435-catalyzed efficient regioselective acetylation of one of the two diastereotopic hydroxymethyl functions in 3-O-benzyl-4-C-hydroxymethyl-1,2- O-isopropylidene-α-d-ribofuranose has been achieved. The enzymatic methodology has been successfully utilized for convergent synthesis of bicyclic nucleosides (LNA monomers) T, U, A, and C. Further, it has been demonstrated that Novozyme-435 can be used for 10 cycles of the acylation reaction without losing selectivity and efficiency.

U2 - 10.1021/jo5008338

DO - 10.1021/jo5008338

M3 - Journal article

C2 - 24901539

SN - 0022-3263

VL - 79

SP - 6336

EP - 6341

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 13

ER -