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HRID653323

反应详情

EQUATION

反应方程式

HRID 653323 的结构方程式

REACTANTS

反应物

4
结构：O=C([O-])[O-].[Cs+].[Cs+]
HCID10796

Cesium carbonate

CCs2O3

结构：COC(=O)CCS
HCID18050

Methyl 3-mercaptopropionate

C4H8O2S

2 次

结构：CC(C)CC(C)(C)C.CCOC(C)=O
HCID18516502

未命名化合物

结构：CC(=O)OC[C@H]1O[C@H](O[C@@H]2[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@H](OCCBr)O[C@@H]2COC(C)=O)[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@H]1OC(C)=O
HCID22887090

未命名化合物

PRODUCTS

生成物

1
结构：COC(=O)CCSCCO[C@@H]1O[C@H](COC(C)=O)[C@H](O[C@H]2O[C@H](COC(C)=O)[C@H](OC(C)=O)[C@H](OC(C)=O)[C@H]2OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O
HCID54172652

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

3
结构：CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC.[Cl-]
催化剂HCID21218

未命名化合物

结构：c1ccccc1
溶剂HCID241

Benzene

C6H6

结构：O
溶剂HCID962

Water

H2O

PROCEDURE

实验过程

2-Bromoethyl 2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-β-D-galactopyranoside (15) (251 mg; 0.338 mmol), methyl 3-mercaptopropionate (38 μl; 0.35 mmol) methyltrioctylammonium chloride (ca 10 mg) and cesium carbonate (114 mg; 0.35 mmol) were dissolved in benzene (0.5 ml) and water (0.5 ml). The reaction mixture was stirred (magnet) over night and analyzed by TLC (SiO2, ethyl acetate:isooctane 4:1; reaction 2/3 completed). Methyl 3-mercaptopropionate (ca 20 μl) was added and the reaction mixture was stirred for 24 h (TLC showed complete reaction). The phases were separated, the water phase was extracted twice with methylene chloride and the combined organic phases were dried (sodium sulfate) which gave a yellow to green solution. Evaporation gave a syrup which was chromatographed (SiO2, ethyl acetate:isooctane 2:1) to give the title compound (22) as a syrup. Yield: 211 mg (80%). [α]D23 +70.0° (c 0.6; CHCl3); 1H-NMR (CDCl3, TMS) δ 5.57 (d, 1H, J3',4' =3.0 Hz, H4'), 5.39 (dd, 1H, J2',3' =11.0 Hz. H2'), 5.19 (dd, 1H, H3'), 5.17 (dd, 1H, J2,3 =11 Hz, H2), 5.00 (d, 1H, J1',2' =4.0 Hz, H1'), 4.80 (dd, 1H, J3,4 =3.0 Hz, H3), 4.51 (d, 1H, J1,2 =8.0 Hz, H1), 3.70 (s, 3H, CH3 --O), 2.82, 2.75, 2.63 (t, 2H each, J=7 Hz, CH2 --S, CH2 --CO), 2.13, 2.11, 2.08, 2.08, 2.06, 2.04, 1.98 (s, 3H each, CH3CO) ppm. 13C-NMR (CDCl3, TMS) δ 172.3 (COOCH3), 170.7, 170.6, 170.5, 170.4, 170.1, 169.8, 169.2 (CH3CO), 101.1 (Cl), 99.4 (Cl'), 77.1, 72.7, 72.0, 68.6, 68.5, 67.9, 67.4, 67.1 (C2-C5, C2'-C5'), 69.5 (OCH2), 62.0, 60.5 (C6, C6'), 51.8 (COOCH3), 34.7, 31.4, 27.4 (CH2S, CH2 --CO), 21.0, 20.7 (CH3CO) ppm.

WORKUP

后处理

  1. stirringthe reaction mixture was stirred for 24 h
  2. custom(TLC showed complete reaction)
  3. customThe phases were separated
  4. extractionthe water phase was extracted twice with methylene chloride
  5. dry with materialthe combined organic phases were dried (sodium sulfate) which
  6. customgave a yellow to green solution
  7. customEvaporation
  8. customgave a syrup which
  9. customwas chromatographed (SiO2, ethyl acetate:isooctane 2:1)