Chemoenzymatic synthesis of C-4^'-Spiro-oxetanoribonucleosides

TY - JOUR

T1 - Chemoenzymatic synthesis of C-4'-Spiro-oxetanoribonucleosides

AU - Sharma, Vivek

AU - Kumar, Manish

AU - Sharma, Deepti

AU - Olsen, Carl Erik

AU - Prasad, Ashok K.

PY - 2014/9/19

Y1 - 2014/9/19

N2 - Novozyme-435-mediated diastereoselective deacylation of one of the two diastereotopic acyloxymethyl groups in 5-O-acyl-4-C-acyloxymethyl-3-O-benzyl-1,2-O-isopropylidene-a-D-ribofuranose has been achieved in quantitative yield. The exclusive selectivity of the lipase for the 5-O-acyl over the 4-C-acyloxymethyl group in the substrate was confirmed by chemical transformation of enzymatically monodeacetylated compound to 1,2-O-isopropylidene-C-4-spiro-oxetanoribofuranose. Further, the selective biocatalytic deacylation methodology has been utilized for the efficient synthesis of C-4'-spiro-oxetanoribonucleosides of uracil(U)and thymine(T)in 37 and 45% overall yields, respectively.

AB - Novozyme-435-mediated diastereoselective deacylation of one of the two diastereotopic acyloxymethyl groups in 5-O-acyl-4-C-acyloxymethyl-3-O-benzyl-1,2-O-isopropylidene-a-D-ribofuranose has been achieved in quantitative yield. The exclusive selectivity of the lipase for the 5-O-acyl over the 4-C-acyloxymethyl group in the substrate was confirmed by chemical transformation of enzymatically monodeacetylated compound to 1,2-O-isopropylidene-C-4-spiro-oxetanoribofuranose. Further, the selective biocatalytic deacylation methodology has been utilized for the efficient synthesis of C-4'-spiro-oxetanoribonucleosides of uracil(U)and thymine(T)in 37 and 45% overall yields, respectively.

U2 - 10.1021/jo501655j

DO - 10.1021/jo501655j

M3 - Journal article

SN - 0022-3263

VL - 79

SP - 8516

EP - 8521

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 18

ER -