1,2,3,5-Tetra-O-benzoyl-2-C-methyl-beta-D-ribofuranose → 4-amino-1-(3,4-dibenzoyloxy-5-benzoyloxymethyl-3-methyl-tetrahydrofuran-2-yl)-1H-pyrimidin-2-one

HRID 272271Notes

Reaction equation

[NH:1]1[CH:8]=[CH:7][C:5]([NH2:6])=[N:4][C:2]1=[O:3].Cl[Sn](Cl)(Cl)Cl.C(#N)C.C(O[C@@H:26]1[O:48][C@H:47]([CH2:49][O:50][C:51](=[O:58])[C:52]2[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=2)[C@@H:37]([O:38][C:39](=[O:46])[C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[C@@:27]1([CH3:59])[O:28][C:29](=[O:36])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)(=O)C1C=CC=CC=1>>[NH2:6][C:5]1[CH:7]=[CH:8][N:1]([CH:26]2[C:27]([O:28][C:29](=[O:36])[C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)([CH3:59])[CH:37]([O:38][C:39](=[O:46])[C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)[CH:47]([CH2:49][O:50][C:51](=[O:58])[C:52]3[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=3)[O:48]2)[C:2](=[O:3])[N:4]=1

Participants

Reactant 3

HCID 108755601,2,3,5-Tetra-O-benzoyl-2-C-methyl-beta-D-ribofuranose

HCID 12271879SnCl4 acetonitrile

HCID 178418229Cytosine

Product 1

HCID 671753714-amino-1-(3,4-dibenzoyloxy-5-benzoyloxymethyl-3-methyl-tetrahydrofuran-2-yl)-1H-pyrimidin-2-one

Procedure

In one synthesis method, depicted in FIG. 1a, the synthesis comprises reacting cytosine, BSA and SnCl4/acetonitrile with 1,2,3,5-tetra-O-benzoyl-2-C-methyl-β-D-ribofuranose (1) to form 4-amino-1-(3,4-dibenzoyloxy-5-benzoyloxymethyl-3-methyl-tetrahydro-furan-2-yl)-1H-pyrimidin-2-one (2); and reacting (2) with NaOMe/MeOH to provide 4-amino-1-(3,4-dihydroxy-5-hydroxymethyl-3-methyl-tetrahydro-furan-2-yl)-1H-pyrimidin-2-one (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.

Workup

customIn one synthesis method

Sources & evidence

ORD record: ord-31ae4cdf337c4ec48a0bef996a7ecb8b
Source dataset: uspto-grants-2008_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07456155B2

Reaction notes

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