Tubercidin → 7-(2'-C-methyl-beta-D-ribofuranosyl)-4-amino-5-(formyl)-pyrrolo[2,3-d]pyrimidine

HRID 1270050Notes

Reaction equation

[CH3:1][C@@:2]1([OH:20])[C@H:6]([OH:7])[C@@H:5]([CH2:8][OH:9])[O:4][C@H:3]1[N:10]1[C:14]2[N:15]=[CH:16][N:17]=[C:18]([NH2:19])[C:13]=2[CH:12]=[CH:11]1.C1C2=C(N)N=CN=C2N([C@@H]2[O:35][C@H:34](CO)[C@@H](O)[C@H]2O)C=1>>[CH3:1][C@@:2]1([OH:20])[C@H:6]([OH:7])[C@@H:5]([CH2:8][OH:9])[O:4][C@H:3]1[N:10]1[C:14]2[N:15]=[CH:16][N:17]=[C:18]([NH2:19])[C:13]=2[C:12]([CH:34]=[O:35])=[CH:11]1

Participants

Reactant 2

HCID 6245Tubercidin

HCID 30118937-Deaza-2'-C-methyladenosine

Product 1

HCID 114040547-(2'-C-methyl-beta-D-ribofuranosyl)-4-amino-5-(formyl)-pyrrolo[2,3-d]pyrimidine

Procedure

7-(2′-C-methyl-β-D-ribofuranosyl)-4-amino-5-(formyl)-pyrrolo[2,3-d]pyrimidine was synthesized according to the procedure described by Shin-ichi Watanabe and Tohru Ueda in Nucleosides and Nucleotides (1983) 2(2), 113–125. In the synthesis of the title compound however, 7-(2′-C-methyl-β-D-ribofuranosyl)-4-amino-pyrrolo[2,3-d]pyrimidine (See Carroll, et al.,11,12) was substituted in place of tubercidin.

Workup

custom7-(2′-C-methyl-β-D-ribofuranosyl)-4-amino-5-(formyl)-pyrrolo[2,3-d]pyrimidine was synthesized

Sources & evidence

ORD record: ord-505413b4a1994b46b7c853c4d17253d7
Source dataset: uspto-grants-2007_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07202223B2

Reaction notes

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