Succinic anhydride → HCID 89999082, compound

HRID 2273335Notes

Reaction equation

HRID 2273335 reaction equation
[C:1]1(=[O:7])[O:6][C:4](=[O:5])[CH2:3][CH2:2]1.[CH3:8][O:9][C:10]1[CH:57]=[CH:56][C:13]([CH2:14][O:15][C@@H:16]2[C@@H:23]([CH2:24][OH:25])[O:22][C@H:19]([O:20][CH3:21])[C@H:18]([O:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40])[C@H:17]2[O:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH3:55])=[CH:12][CH:11]=1>CN(C1C=CN=CC=1)C.N1C=CC=CC=1>[C:4]([CH2:3][CH2:2][C:1]([O:25][CH2:24][C@H:23]1[O:22][C@H:19]([O:20][CH3:21])[C@H:18]([O:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40])[C@@H:17]([O:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH3:55])[C@@H:16]1[O:15][CH2:14][C:13]1[CH:12]=[CH:11][C:10]([O:9][CH3:8])=[CH:57][CH:56]=1)=[O:7])([OH:6])=[O:5]

Participants

5

Reactant 2

HCID 7922Succinic anhydrideHCID 69040178HCID 69040178, compound

Product 1

HCID 89999082HCID 89999082, compoundYield 89.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

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

  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)

Sources & evidence

ORD record
ord-9a7ca8ba06fa472f9fcdf3acb52076eb
Source dataset
uspto-grants-2015_09
Patent number
US09120838B2

Reaction notes

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