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HRID2273335

反应详情

EQUATION

反应方程式

HRID 2273335 的结构方程式

REACTANTS

反应物

2
结构：O=C1CCC(=O)O1
HCID7922

Succinic anhydride

C4H4O3

结构：CCCCCCCCCCCCCCO[C@@H]1[C@@H](OCCCCCCCCCCCCCC)[C@@H](OC)O[C@H](CO)[C@H]1OCc1ccc(OC)cc1
HCID69040178

未命名化合物

PRODUCTS

生成物

1
结构：CCCCCCCCCCCCCCO[C@@H]1[C@@H](OCCCCCCCCCCCCCC)[C@@H](OC)O[C@H](COC(=O)CCC(=O)O)[C@H]1OCc1ccc(OC)cc1
HCID89999082

未命名化合物

收率 89.3%

AUXILIARIES

试剂、催化剂与溶剂

2
结构：CN(C)c1ccncc1
催化剂HCID14284

N,N-Dimethylpyridin-4-amine

C7H10N2

结构：c1ccncc1
溶剂HCID1049

Pyridine

C5H5N

PROCEDURE

实验过程

DMAP (7.0 mg, 0.05 mmol) and succinic anhydride (71 mg, 0.70 mmol) were added to a stirred solution of methyl 4-O-p-methoxybenzyl-2,3-di-O-tetradecanyl-α-D-glucopyranoside 21 (Price et al., Proc. Natl. Acad. Sci., USA, 1995, 92, 7352-7356) (0.40 g, 0.56 mmol) in dry pyridine (5 mL) and the resulting reaction mixture was stirred for 16 h at rt under argon. After that, the reaction mixture was concentrated under the reduced pressure. The residue was dissolved in CH2Cl2 (30 mL) and washed successively with 1N HCl (2×15 mL), water (2×15 mL) and brine (15 mL). The organic phase was separated, dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by column chromatography on silica gel (ethyl acetate-hexane gradient elution) to give the title compound 22 (0.41 g, 0.50 mmol) as a colorless syrup in 89% yield. Analytical data for 22: Rf=0.55 (ethyl acetate/hexane, 7/3, v/v); [α]D24+42.9° (c=1.0, CHCl3); 1H NMR (300 MHz, CDCl3): δ, 0.88 (t, 6H, 2×CH3), 1.26 (br. s, 40H, 22×CH2), 1.63 (m, 4H, 2×CH2), 2.64 (m, 2H, 2×CH2), 3.30 (dd, 1H, J2,3=9.7 Hz, H-2), 3.38 (s, 3H, OCH3), 3.39 (m, H-4), 3.59-3.76 (m, 5H, H-3, 5, OCH2, OCH2a), 3.80 (s, 3H, OCH3), 3.86 (m, 1H, OCH2b), 4.28 (m, 2H, J5,6b=4.7 Hz, J5,6a=2.3 Hz, J6a,6b=12.0 Hz, H-6a, 6b), 4.49 (d, 1H, J2=10.5 Hz, ½CH2Ph), 4.76 (d, 1H, J1,2=3.5 Hz, H-1), 4.81 (d, 1H, J2=10.5 Hz, ½CH2Ph), 6.89 (d, 2H, J=8.9 Hz, aromatic), 7.22 (d, 2H, J=9.7 Hz, aromatic) ppm; 13C NMR (125 MHz, CDCl3): δ=14.3, 22.9, 26.2, 26.5, 28.8, 28.9, 29.5, 29.7, 29.8, 29.9 (×2), 30.3, 30.8, 32.1, 55.3, 55.5, 63.6, 68.8, 72.0, 74.1, 74.8, 80.9, 81.9, 98.1, 114.1, 130.1, 130.4, 159.6, 172.0, 176.5 ppm; HR FAB MS [M+Na]+ calcd for C47H82O10Na 829.5805. found 829.5806.

WORKUP

后处理

  1. customthe resulting reaction mixture
  2. concentrationAfter that, the reaction mixture was concentrated under the reduced pressure
  3. dissolutionThe residue was dissolved in CH2Cl2 (30 mL)
  4. washwashed successively with 1N HCl (2×15 mL), water (2×15 mL) and brine (15 mL)
  5. customThe organic phase was separated
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by column chromatography on silica gel (ethyl acetate-hexane gradient elution)