L-Ribose → (2R,3S,4S,5S)-5-(acetoxymethyl)tetrahydrofuran-2,3,4-triyl triacetate

HRID 1944804Notes

Reaction equation

[C:1]([O:4][CH:5]1[O:17][C@@H:16]([CH2:18][O:19][C:20](=[O:22])[CH3:21])[C@H:11]([O:12][C:13](=[O:15])[CH3:14])[C@@H:6]1[O:7][C:8](=[O:10])[CH3:9])(=[O:3])[CH3:2].O=C[C@H]([C@H]([C@H](CO)O)O)O>>[C:1]([O:4][C@H:5]1[O:17][C@@H:16]([CH2:18][O:19][C:20](=[O:22])[CH3:21])[C@H:11]([O:12][C:13](=[O:15])[CH3:14])[C@@H:6]1[O:7][C:8](=[O:10])[CH3:9])(=[O:3])[CH3:2]

Participants

Reactant 2

HCID 90428L-Ribose

HCID 114934341,2,3,5-tetra-O-acetyl-L-ribofuranose

Product 1

HCID 908100(2R,3S,4S,5S)-5-(acetoxymethyl)tetrahydrofuran-2,3,4-triyl triacetate

Procedure

The same operations as those of Example B2 were carried out with the exception that the half-scale (corresponding to 20 mmol of L-ribose) was used and that diisopropyl ether was not added. As a result, 5.82 g of crude 1,2,3,5-tetra-O-acetyl-L-ribofuranose was obtained in the form of yellow oil. The obtained compound was analyzed by HPLC. As a result, it was found that the crude product contained 2.82 g of 1,2,3,5-tetra-O-acetyl-L-ribofuranose, that the ratio of α/β-anomers was 19/81, and that the total reaction yield of the β-anomer from L-ribose was 36%.

Sources & evidence

ORD record: ord-feaa0afaab964e80abfc2159351fb8b4
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08394935B2

Reaction notes

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