2908. d-2-Deoxyribose

Nomenclature

CAS number: 533-67-5
2-Deoxy-d-erythro-pentose; desoxyribose; d-2-deoxyarabinose; d-2-ribodesose; d-erythro-2-deoxypentose; thyminose.
C5H10O4; mol wt 134.13.
C 44.77%, H 7.51%, O 47.71%.

Description and references

Isoln from deoxyribonucleic acid by acidic hydrolysis of purine deoxyribonucleosides which have been isolated by ion-exchange resin chromatography: Laland, Overend, Acta Chem. Scand. 8, 192 (1954). Synthesis: Felton, Freudenberg, J. Am. Chem. Soc. 57, 1637 (1935); Deriaz et al., J. Chem. Soc. 1949, 1879, 2836; Hough, Chem. Ind. (London) 1951, 406; Sowden, Biochem. Prep. 5, 75 (1957); I. Ziderman, E. Dimant, J. Org. Chem. 32, 1267 (1967); J. R. Hauske, H. Rapoport, ibid. 44, 2472 (1979); T. Harada, T. Mukaiyama, Chem. Lett. 1981, 1109. Review: Overend, Stacey, in Chargaff-Davidson, Nucleic Acids vol. 1, E. Chargaff, N. J. Davidson, Eds. (Academic Press, New York, 1955) pp 1-80.

Chemical structure

Properties

Crystals from isopropanol, mp 91°. Shows mutarotation. Final [α]D22 -56.2° (H2O). Sol in water, pyridine. Slightly sol in alc.

Derivative

1,3,4-Triacetate.
C11H16O7; mol wt 260.24.
C 50.77%, H 6.20%, O 43.04%.

Properties

Needles from methanol, mp 98°. [α]D23 -171.8° (c = 0.56 in chloroform): Allerton, Overend, J. Chem. Soc. 1951, 1480.

Derivative

3,4,5-Triacetate.

Properties

Oily liq, bp0.001 105°. [α]D21 +3.4° (c = 4.57 in pyridine): Zinner et al., Ber. 90, 2696 (1957).

Derivative

1,3,4-Tribenzoate.

Properties

Small white nodules from ethanol, mp 127°. [α]D23 -65° (c = 1.02 in chloroform) (Allerton, Overend). Probably a mixture of the two anomeric 2-deoxy-d-ribopyranose tribenzoates: Pedersen et al., J. Am. Chem. Soc. 82, 3425 (1960).

Derivative

3,4,5-Tribenzoate.

Properties

Fine needles from ethyl acetate + petr ether, mp 118-119°. [α]D18 -2.8° (c = 1.44 in pyridine) (Zinner).