1-(beta-D-Ribofuranosyl)pyrrole-2-carbaldehyde → 4-Propynyl-1-(beta-D-ribofuranosyl)pyrrole-2-carbaldehyde

HRID 1662295Notes

Reaction equation

HRID 1662295 reaction equation
[C@@H:1]1([N:10]2[CH:14]=[CH:13][CH:12]=[C:11]2[CH:15]=[O:16])[O:7][C@H:6]([CH2:8][OH:9])[C@@H:4]([OH:5])[C@H:2]1[OH:3].[C:17]([C:20]1C=C(C=O)NC=1)#[C:18]C>>[C:18]([C:13]1[CH:12]=[C:11]([CH:15]=[O:16])[N:10]([C@@H:1]2[O:7][C@H:6]([CH2:8][OH:9])[C@@H:4]([OH:5])[C@H:2]2[OH:3])[CH:14]=1)#[C:17][CH3:20]

Participants

3

Reactant 2

HCID 444333061-(beta-D-Ribofuranosyl)pyrrole-2-carbaldehydeHCID 450792014-Propynylpyrrole-2-carbaldehyde2×

Product 1

HCID 866390144-Propynyl-1-(beta-D-ribofuranosyl)pyrrole-2-carbaldehyde

Procedure

4-Propynyl-1-(β-D-ribofuranosyl)pyrrole-2-carbaldehyde (Compound 18) was synthesized in the same manner as used for Compound 17, starting with 4-propynyl-2-pyrrolecarbaldehyde (Compound 16) (Non-patent Document 40) (266 mg, 2.0 mmol). After purification by RP-HPLC, Compound 18 was obtained (39 mg, 7%, 2 steps).

Workup

  1. custom4-Propynyl-1-(β-D-ribofuranosyl)pyrrole-2-carbaldehyde (Compound 18) was synthesized in the same manner
  2. customAfter purification by RP-HPLC

Sources & evidence

ORD record
ord-95b5060e29264edd80ee125312182c2c
Source dataset
uspto-grants-2011_10
Patent number
US08030478B2

Reaction notes

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