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

HRID 964722노트

반응식

HRID 964722 반응식
[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

참가 물질

3

반응물 1

HCID 86752823HCID 86752823, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 86607755Acetic acid methanol water용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-39127010b2a043af846625fa5dfb7dba
출처 데이터셋
uspto-grants-1998_06
특허 번호
US05770713

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