Reaction #1951046

Reaction equation

compound 1

1,2,3,5-tetra-O-benzoyl-2-C-methyl-β-D-ribofuranose

cytosine

SnCl4 acetonitrile

1,2,3,5-tetra-O-benzoyl-2-C-methyl-β-D-ribofuranose

→

compound 2

4-amino-1-(3,4-dibenzoyloxy-5-benzoyloxymethyl-3-methyl-tetrahydro-furan-2-yl)-1H-pyrimidin-2-one

Conditions

Workup

1. 1
   OtherIn one synthesis method

Procedure

In one synthesis method, depicted in FIG. 5, the synthesis comprises reacting cytosine, BSA and SnCl4/acetonitrile with 1,2,3,5-tetra-O-benzoyl-2-C-methyl-β-D-ribofuranose (FIG. 5, compound 1) to form 4-amino-1-(3,4-dibenzoyloxy-5-benzoyloxymethyl-3-methyl-tetrahydro-furan-2-yl)-1H-pyrimidin-2-one (FIG. 5, compound 2); and reacting (FIG. 5, compound 2) with NaOMe/MeOH to provide 4-amino-1-(3,4-dihydroxy-5-hydroxymethyl-3-methyl-tetrahydro-furan-2-yl)-1H-pyrimidin-2-one (FIG. 5, compound 3), also known as 2-C-methyl-β-D-ribofuranose. The use of cytosine as a starting material rather than benzoyl-cytosine improves the “atom economy” of the process and simplifies purification at later steps.

Source