HCID 86752823、化合物 → O-(Thymidin-3'-yl) O-(thymidin-5'-yl) S-(pivaloyloxymethyl) phosphorothioate

HRID 964722ノート

反応式

HRID 964722 の反応式
[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

参加物

3

反応物 1

HCID 86752823HCID 86752823、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 86607755Acetic acid methanol water溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-39127010b2a043af846625fa5dfb7dba
出典データセット
uspto-grants-1998_06
特許番号
US05770713

反応ノート

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