Acetaldehyde → HCID 22863203, compound

HRID 1739391Notes

Reaction equation

HRID 1739391 reaction equation
CON=[CH:4][C@@H:5]1[C@@H:9]([CH2:10][O:11][N:12]2[C:16](=[O:17])[C:15]3=[CH:18][CH:19]=[CH:20][CH:21]=[C:14]3[C:13]2=[O:22])[O:8][C@@H:7]([N:23]2[CH:31]=[C:29]([CH3:30])[C:27](=[O:28])[NH:26][C:24]2=[O:25])[CH2:6]1.CC=[O:34]>CO>[CH:4]([C@@H:5]1[C@@H:9]([CH2:10][O:11][N:12]2[C:16](=[O:17])[C:15]3=[CH:18][CH:19]=[CH:20][CH:21]=[C:14]3[C:13]2=[O:22])[O:8][C@@H:7]([N:23]2[CH:31]=[C:29]([CH3:30])[C:27](=[O:28])[NH:26][C:24]2=[O:25])[CH2:6]1)=[O:34]

Participants

4

Reactant 2

HCID 177AcetaldehydeHCID 53708600HCID 53708600, compound

Product 1

HCID 22863203HCID 22863203, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3'-Deoxy-3'-C-[(methoxyimino)methyl]-5'-O-phthalimidothymidine upon treated with CH3CHO in MeOH regenerated the 3'-C-formyl group. The product on purification by silica gel column chromatography furnished the title compound as homogeneous material in 81% overall yield for 3 steps. 1H NMR (CDCl3) δ 9.95 (s, 1, CH=O); 8.62 (br s, 1, NH); 7.71-7.90 (m, 5, aromatic H, H-6); 6.06 (t, 1, H-1', J1'2' =6.61 Hz, J1'2' =6.6 Hz); 4.36-4.73 (m, 3, H-4', H5',5"); 3.78 (m, 1, H-3'); 2.20-2.90 (m, 2, H-2'2"); 1.98 (s, 3, C5CH3).

Workup

  1. customThe product on purification by silica gel column chromatography

Sources & evidence

ORD record
ord-7755a577f85846c88f4fe45d796a64a3
Source dataset
uspto-grants-1999_10
Patent number
US05965721

Reaction notes

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