HCID 86752823, Verbindung → O-(Thymidin-3'-yl) O-(thymidin-5'-yl) S-(pivaloyloxymethyl) phosphorothioate

HRID 964722Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 964722
[P:1](=[O:93])([S:84][CH2:85][O:86][C:87](=[O:92])[C:88]([CH3:91])([CH3:90])[CH3:89])([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:93])([S:84][CH2:85][O:86][C:87](=[O:92])[C:88]([CH3:91])([CH3:90])[CH3:89])([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

Komponenten

3

Edukt 1

HCID 86752823HCID 86752823, Verbindung

Produkt 1

HCID 67649043O-(Thymidin-3'-yl) O-(thymidin-5'-yl) S-(pivaloyloxymethyl) phosphorothioate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 86607755Acetic acid methanol waterLösungsmittel

Versuchsvorschrift

The totally protected dimeric phosphorothioate triester (3a) is dissolved in a mixture of acetic acid/water/methanol (8:1:1, v:v:v) (10 ml). The reaction is left with stirring at ambient temperature for 5 hours. The reaction medium is then evaporated and the residue is coevaporated several times with water and toluene. The residue is then chromatographed on a silica gel column using a gradient of methanol (0 to 10%) in dichloro-methane as eluent. The fractions containing the product (4a) are collected, concentrated under reduced pressure, and then the residue is coevaporated several times with dioxane and lyophilized in dioxane. (4a) is obtained in the form of a white powder (98 mg, 85%).

Aufarbeitung

  1. waitThe reaction is left
  2. customThe reaction medium is then evaporated
  3. customThe residue is then chromatographed on a silica gel column
  4. additionThe fractions containing the product (4a)
  5. customare collected
  6. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-39127010b2a043af846625fa5dfb7dba
Quelldatensatz
uspto-grants-1998_06
Patentnummer
US05770713

Notizen zur Reaktion

Wird geladen…