An efficient approach to homochiral indane nucleosides

A series of new chiral 6-substituted purinyl and 8-aza-purinyl carbonucleosides based on indanol were synthesized from the commercially available (1R,2S)-1-amino-2-indanol and (1S,2R)-1-amino-2-indanol based on a well-known methodology.

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(1R,2S)-1-(2-Amino-6-chloro-pyrimidin-4-ylamino)-indan-2-olC13H13ClN4O[α]D23=-37.5 (c 0.530, MeOH)Chirality source: (1R,2S)-(+)-cis-1-amino-2-indanolAbsolute configuration: (1R,2S)

(1R,2S)1-[2-Amino-6-chloro-5-(4-chloro-phenylazo)-pyrimidin-4-ylamino]-indan-2-olC19H16Cl2N6O[α]D23=+42.3 (c 0.180, MeOH)Chirality source: (1R,2S)-(+)-cis-1-amino-2-indanolAbsolute configuration: (1R,2S)

(1R,2S)-1-(2,5-Diamino-6-chloro-pyrimidin-4-ylamino]-indan-2-olC13H14ClN5O[α]D23=-1.6(c 0.257, MeOH)Chirality source: (1R,2S)-(+)-cis-1-amino-2-indanolAbsolute configuration: (1R,2S)

(1R,2S)-1-(2-Amino-6-chloro-9H-purin-9-yl)-2,3-dihydro-1H-inden-2-olC14H12ClN5O[α]36523=+38.1 (c 0.01, MeOH)Chirality source: (1R,2S)-(+)-cis-1-amino-2-indanolAbsolute configuration: (1R,2S)

2-Amino-9-[(1R,2S)-2-hydroxy-2,3-dihydro-1H-inden-1-yl]-1H-purin-6(9H)-oneC14H13N5O2[α]D23=+20.5 (c 0.203, MeOH)Chirality source: (1R,2S)-(+)-cis-1-amino-2-indanolAbsolute configuration: (1R,2S)

(1R,2S)-1-(5-Amino-7-chloro-3H-[1,2,3]triazolo[4,5-d]pyrimidin-3-yl)-2,3-dihydro-1H-inden-2-olC13H11ClN6O[α]D23=-1.5 (c 0.501, MeOH)Chirality source: (1R,2S)-(+)-cis-1-amino-2-indanolAbsolute configuration: (1R,2S)

5-Amino-3-[(1R,2S)-2-hydroxy-2,3-dihydro-1H-inden-1-yl]-3H-[1,2,3]triazolo[4,5-d]pyrimidin-7(6H)-oneC13H12N6O2[α]D23=-12.6 (c 0.150, MeOH)Chirality source: (1R,2S)-(+)-cis-1-amino-2-indanolAbsolute configuration: (1R,2S)

9-[(1R,2S)-2-Hydroxy-indan-1-yl]-1,9-dihydro-purin-6-oneC14H12N4O2[α]D23=-28.2 (c 0.137, MeOH)Chirality source: (1R,2S)-(+)-cis-1-amino-2-indanolAbsolute configuration: (1R,2S)

(1R,2S)-1-(5-Amino-6-chloro-pyrimidin-4-ylamino)-indan-2-olC13H13ClN4O[α]D23=+76.6 (c 0.419, MeOH)Chirality source: (1R,2S)-(+)-cis-1-amino-2-indanolAbsolute configuration: (1R,2S)

(1R,2S)-1-(6-Chloro-purin-9-yl)-indan-2-olC14H11ClN4O[α]D23=+110.2 (c 0.108, MeOH)Chirality source: (1R,2S)-(+)-cis-1-amino-2-indanolAbsolute configuration: (1R,2S)

3-[(1R,2S)-2-Hydroxy-indan-1-yl]-3,6-dihydro-[1.2.3]triazolo[4,5-d]pyrimidin-7-oneC13H11N5O2[α]D23=-9.0 (c 0.110, MeOH)Chirality source: (1R,2S)-(+)-cis-1-amino-2-indanolAbsolute configuration: (1R,2S)