HCID 86753031, compound → HCID 18664733, compound

HRID 482306Notes

Reaction equation

HRID 482306 reaction equation
C([O:8][C:9](=[O:45])[C@H:10]([CH2:24][O:25][C@H:26]1[O:43][C@@H:42]([CH3:44])[C@@H:37]([O:38][C:39](=[O:41])[CH3:40])[C@@H:32]([O:33][C:34](=[O:36])[CH3:35])[C@@H:27]1[O:28][C:29](=[O:31])[CH3:30])[N:11](OC(=O)C1C=CC=CC=1)C(O)=O)C1C=CC=CC=1>C(O)C.[Pd]>[C:29]([O:28][C@H:27]1[C@H:32]([O:33][C:34](=[O:36])[CH3:35])[C@H:37]([O:38][C:39](=[O:41])[CH3:40])[C@H:42]([CH3:44])[O:43][C@@H:26]1[O:25][CH2:24][C@@H:10]([C:9]([OH:45])=[O:8])[NH2:11])(=[O:31])[CH3:30]

Participants

4

Reactant 1

HCID 86753031HCID 86753031, compound

Product 1

HCID 18664733HCID 18664733, compoundYield 81.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of N-Carboxybenzoyloxy-3-O-(2,3,4-tri-O-acetyl-β-L-fucopyranosyl)-L-serine Benzyl Ester (600 mg, 1.0 mmol) in 98% ethanol (15 ml) containing 5% Pd/C (300 mg) was hydrogenated for 16 h at room temperature and at 1 atmospheric pressure. The catalyst was collected on celite and washed with several portions of 98% ethanol. The filtrate and washings were combined and concentrated to dryness to give 3-O-(2,3,4-tri-O-acetyl-β-L-fucopyranosyl)-L-serine (306.6 mg, 81.6%) as a white powder Rf =0.34 (dichloromethane:methanol:water, 60:35:3). 1H-NMR (CD3OD): ε 5.23 (dd, 1 H, J3,4 =3.0, J4,5 =1.0 Hz, H-4), 5.14-5.02 (m, 2 H, H-2 and 3), 4.68 (d, 1 H, J1,2 =7.5 Hz, H-1), 4.24 (dd, 1 H, Jgem =7.5 Hz, H-1), 4.24 (dd, 1 H, Jgem =10.5, JCH,CHN =2.0 Hz, serine CH), 4.13-4.04 (m, 2 H, serine CHH and CHN), 4.01 (dq, J5,6 =6.5 Hz, H-5), 2.13, 2.05 and 1.93 (each s, 3 H, Ac), 1.19 (d, 3 H, H-6). N-(9-Fluorenylmethyloxycarbonyl)-3-O-(2,3,4-tri-O-acetyl-β-L-fucopyranosyl)-L-serine (FIG. 1E).

Workup

  1. customThe catalyst was collected on celite
  2. washwashed with several portions of 98% ethanol
  3. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-99c78bddea12431597f661a935e19a9d
Source dataset
uspto-grants-1998_08
Patent number
US05795958

Reaction notes

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