HCID 86752825, compound → HCID 86752824, compound

HRID 964723Notes

Reaction equation

HRID 964723 reaction equation
[P:1](=[O:90])([S:84][CH2:85][S:86][C:87](=[O:89])[CH3:88])([O:43][CH:44]([OH:83])[C@H:45]1[O:49][C@@H:48]([N:50]2[CH:58]=[C:56]([CH3:57])[C:54](=[O:55])[NH:53][C:51]2=[O:52])[CH2:47][C@@H:46]1[O:59]C(C1C=CC=CC=1)(C1C=CC(OC)=CC=1)C1C=CC(OC)=CC=1)[O:2][C@@:3]1([OH:42])[C@@H:7]([CH2:8][O:9]C(C2C=CC=CC=2)(C2C=CC(OC)=CC=2)C2C=CC(OC)=CC=2)[O:6][C@@H:5]([N:33]2[CH:41]=[C:39]([CH3:40])[C:37](=[O:38])[NH:36][C:34]2=[O:35])[CH2:4]1>C(O)(=O)C.O.CO>[P:1](=[O:90])([S:84][CH2:85][S:86][C:87](=[O:89])[CH3:88])([O:43][CH:44]([OH:83])[C@H:45]1[O:49][C@@H:48]([N:50]2[CH:58]=[C:56]([CH3:57])[C:54](=[O:55])[NH:53][C:51]2=[O:52])[CH2:47][C@@H:46]1[OH:59])[O:2][C@@:3]1([OH:42])[C@@H:7]([CH2:8][OH:9])[O:6][C@@H:5]([N:33]2[CH:41]=[C:39]([CH3:40])[C:37](=[O:38])[NH:36][C:34]2=[O:35])[CH2:4]1

Participants

3

Reactant 1

HCID 86752825HCID 86752825, compound

Product 1

HCID 86752824HCID 86752824, compound

Reagents, catalysts & solvents 1

HCID 86607755Acetic acid methanol waterSolvent

Procedure

The totally protected phosphorothioate dinucleoside (3c) is dissolved in an acetic acid/water/methanol mixture (8:1:1, v:v:v) (5 ml) and left with stirring at ambient temperature all night. The following day, the reaction mixture is evaporated and coevaporated several times with water and with toluene. The residue is then chromatographed on a column of silica gel using a gradient of methanol (0 to 10%) as eluent. The fractions containing the detritylated phosphorothioate triester dinucleoside (4c) are collected and concentrated under reduced pressure. The residue is coevaporated with dioxane and then lyophilized in dioxane. (4c) is obtained in the form of a white powder (20 mg, 85%).

Workup

  1. waitleft
  2. customThe following day, the reaction mixture is evaporated
  3. customThe residue is then chromatographed on a column of silica gel using a gradient of methanol (0 to 10%) as eluent
  4. additionThe fractions containing the detritylated phosphorothioate triester dinucleoside (4c)
  5. customare collected
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9db869958aad4ba18cccf81cae24ec47
Source dataset
uspto-grants-1998_06
Patent number
US05770713

Reaction notes

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