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HRID653345

反应详情

EQUATION

反应方程式

HRID 653345 的结构方程式

REACTANTS

反应物

4
结构：CN(C)C=O
HCID6228

N,N-Dimethylformamide

C3H7NO

结构：O=C([O-])[O-].[Cs+].[Cs+]
HCID10796

Cesium carbonate

CCs2O3

结构：COC(=O)CCCCCCCCCCS
HCID406973

methyl 11-mercaptoundecanoate

C12H24O2S

结构：CC(=O)OC[C@H]1O[C@H](OC[C@H]2O[C@H](O[C@H]3[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H](O[C@H]4[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@H](OCCBr)O[C@@H]4COC(C)=O)O[C@@H]3COC(C)=O)[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H]2OC(C)=O)[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H]1OC(C)=O
HCID86741646

未命名化合物

PRODUCTS

生成物

1
结构：COC(=O)CCCCCCCCCCSCCO[C@@H]1O[C@H](COC(C)=O)[C@@H](O[C@H]2O[C@H](COC(C)=O)[C@@H](O[C@H]3O[C@H](CO[C@H]4O[C@H](COC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]4OC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]3OC(C)=O)[C@H](OC(C)=O)[C@H]2OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O
HCID86741647

未命名化合物

收率 50%

AUXILIARIES

试剂、催化剂与溶剂

1
结构：ClCCl
溶剂HCID6344

Dichloromethane

CH2Cl2

PROCEDURE

实验过程

Compound 93 (431 mg, 0.33 mmol), methyl 11-mercaptoundecanoate (105, 114 mg, 0.49 mmol), cesium carbonate (128 mg, 0.39 mmol) and N,N-dimethylformamide (3 ml) were stirred at room temperature for 15 h. The mixture was diluted with dichloromethane, washed with water (neutralization with Duolite H+ resin facilitated the phase separation), and dried (Na2SO4). The solvent was removed and the residue was chromatographed (SiO2, ethyl acetate:isooctane 2:1) to give 95 (243 mg, 50%). [α]D24 +91° (c 4.4, chloroform). 1H-NMR (CDCl3, Me4Si) δ 5.36, 5.28, 5.19 (3d, each 1H, J=3.8, 4.1 and 3.6 Hz, H1', H1", H1"'), 4.57 (d, 1H, J=7.9 Hz, H1), 3.67 (s, 3H, MeO), 2.68, 2.52, 2.31 (3 t, each 2H, J=7 Hz, CH2 --S--CH2 and CH2CO). 13C-NMR (CDCl3, Me4Si) δ 174.1, 170.4-169.1, 100.1 (Cl), 95.6, 95.5, 95.1 (Cl', Cl", Cl"'), 75.0, 73.6, 72.5, 71.9, 71.5, 70.5, 70.2, 69.9, 69.7, 69.6, 69.2, 69.1, 69.1, 69.1, 68.7, 68.3, 67.2, 65.1, 62.9, 62.8, 61.6, 51.2, 33.9, 32.3, 31.1, 29.5, 29.2, 29.1, 29.0, 29.0, 28.9, 28.6, 24.7, 20.7-20.4.

WORKUP

后处理

  1. washwashed with water (neutralization with Duolite H+ resin
  2. customthe phase separation), and
  3. dry with materialdried (Na2SO4)
  4. customThe solvent was removed
  5. customthe residue was chromatographed (SiO2, ethyl acetate:isooctane 2:1)