Thymidine → HCID 53960890, compound

HRID 1109091Notes

Reaction equation

HRID 1109091 reaction equation
[C@@H]1(N2C=C(C)C(=O)NC2=O)O[C@H](CO)[C@@H](O)C1.[CH2:18]([O:34][C:35]1[CH:54]=[CH:53][C:38]([C:39](O)([C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)[C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)=[CH:37][CH:36]=1)[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33].C([Cl:58])(=O)C>>[CH2:18]([O:34][C:35]1[CH:54]=[CH:53][C:38]([C:39]([Cl:58])([C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)[C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)=[CH:37][CH:36]=1)[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33]

Participants

4

Reactant 3

HCID 5789ThymidineHCID 6367Acetyl chlorideHCID 67822185HCID 67822185, compound

Product 1

HCID 53960890HCID 53960890, compoundYield 75%

Procedure

In the chemical synthesis of polynucleotide fragments by the triester procedure, chromatographic methods are important for the purification of protected intermediates and for the isolation of the unprotected final product. The chromatographic behavior of the oligomers can be varied within certain limits by protecting groups, generally producing an unspecific change in the total polarity of the molecule. For example, Gortz et al. Angew. Chem. Int. Ed. Engl., 20(8): 681-683 (1981) describe introducing 4-alkoxytrityl groups for hydrophobic protection at the 5'-end of oligonucleotides. These 4-alkoxytrityl groups contain 8, 10, 12, 14, and 16 carbon atoms. Gortz et al. synthesized 4-hexadecyloxytrityl protected thymidine by first treating 4-hexadecyloxytritanol with acetyl chloride to produce 4-hexadecyloxytrityl chloride. The 4-hexadecyloxytrityl chloride was then treated with thymidine in anhydrous pyridine in the presence of 4-dimethylaminopyridine. After various purification and separation procedures, a 75% yield was obtained. This 4-hexadecyloxytrityl protected thymidine was then condensed onto the 5'--O--position of the terminal nucleotide of a support bound oligonucleotide.

Workup

  1. customare important for the purification of protected intermediates and for the isolation of the unprotected final product
  2. customgenerally producing an unspecific change in the total polarity of the molecule
  3. customGortz et al. synthesized 4-hexadecyloxytrityl

Sources & evidence

ORD record
ord-ff1bc0226f8c452d9cffdce4cce3bf82
Source dataset
uspto-grants-1994_06
Patent number
US05319079

Reaction notes

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