Stereoselective synthesis of 2′-deoxynucleoside analogues as building blocks for deoxynucleoside chemistry

Three pairs of enantiomeric 2′-deoxynucleoside analogues 4a, 4b, 4c, 4e and 4d, 4f, respectively, have been synthesized from enantiomerically pure highly functionalized furanoid glycals 2a–d by involving a similar synthetic strategy. These analogues have various well defined stereogenic centres and are useful building blocks for deoxynucleoside chemistry.

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1-[(1′R,3′R,4′S,5′R)-3′-O-Benzyl-2′-deoxy-5′,6′-O-isopropylidene-d-arabinofuranosyl]thymineC21H26N2O6[α]D25=-23.4 (c 1.67, MeOH)Source of chirality: d-glucoseAbsolute configuration : (1′R,3′R,4′S,5′R)

1-[(1′S,3′S,4′R,5′S)-3′-O-Benzyl-2′-deoxy-5′,6′-O-isopropylidene-l-arabinofuranosyl]thymineC21H26N2O6[α]D25=+17.7 (c 0.27, MeOH)Source of chirality: d-galactoseAbsolute configuration: (1′S,3′S,4′R,5′S)

1-[(1′S,3′R,4′R,5′S)-3′-O-Benzyl-2′-deoxy-5′,6′-O-isopropylidene-l-ribofuranosyl]thymineC21H26N2O6[α]D25=-1.9 (c 0.10, MeOH)Source of chirality: d-glucoseAbsolute configuration: (1′S,3′R,4′R,5′S)

1-[(1′R,3′R,4′R,5′S)-3′-O-Benzyl-2′-deoxy-5′,6′-O-isopropylidene-l-ribofuranosyl]thymineC21H26N2O6[α]D26=-10.2 (c 0.40, MeOH)Source of chirality: d-glucoseAbsolute configuration: (1′R,3′R,4′R,5′S)

1-[(1′R,3′S,4′S,5′R)-3′-O-Benzyl-2′-deoxy-5′,6′-O-isopropylidene-d-ribofuranosyl]thymineC21H26N2O6[α]D25=+1.4 (c 0.37, MeOH)Source of chirality: d-galactoseAbsolute configuration: (1′R,3′S,4′S,5′R)

1-[(1′S,3′S,4′S,5′R)-3′-O-Benzyl-2′-deoxy-5′,6′-O-isopropylidene-d-ribofuranosyl]thymineC21H26N2O6[α]D26=+12.1 (c 0.57, MeOH)Source of chirality: d-galactoseAbsolute configuration: (1′S,3′S,4′S,5′R)