N-(9-Fluorenylmethoxycarbonyloxy)succinimide → HCID 11814023, compound

HRID 482307Notes

Reaction equation

HRID 482307 reaction equation
[C:1]([O:4][C@H:5]1[C@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@H:9]([O:15][C:16](=[O:18])[CH3:17])[C@H:8]([CH3:19])[O:7][C@@H:6]1[O:20][CH2:21][C@@H:22]([C:24]([OH:26])=[O:25])[NH2:23])(=[O:3])[CH3:2].C1C(=O)N([O:34][C:35]([O:37][CH2:38][CH:39]2[C:51]3[C:46](=[CH:47][CH:48]=[CH:49][CH:50]=3)[C:45]3[C:40]2=[CH:41][CH:42]=[CH:43][CH:44]=3)=O)C(=O)C1>N1C=CC=CC=1>[CH:50]1[C:51]2[CH:39]([CH2:38][O:37][C:35]([NH:23][C@H:22]([C:24]([OH:26])=[O:25])[CH2:21][O:20][C@H:6]3[O:7][C@@H:8]([CH3:19])[C@@H:9]([O:15][C:16](=[O:18])[CH3:17])[C@@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@@H:5]3[O:4][C:1](=[O:3])[CH3:2])=[O:34])[C:40]3[C:45](=[CH:44][CH:43]=[CH:42][CH:41]=3)[C:46]=2[CH:47]=[CH:48][CH:49]=1

Participants

4

Reactant 2

HCID 134122N-(9-Fluorenylmethoxycarbonyloxy)succinimideHCID 18664733HCID 18664733, compound

Product 1

HCID 11814023HCID 11814023, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 3-O-(2,3,4-tri-O-acetyl-β-L-fucopyranosyl)-L-serine (FIG. 1D) (209.6 mg, 0.82 mmol) and Fmoc N-hydroxysuccinimide ester (9-fluorenylmethyl-N-succinimidyl carbonate) (375.7 mg, 1.63 mmol) in dry pyridine (25 ml) was stirred for 15 h at room temperature. Evaporation and co-evaporation of the reaction mixture with toluene left a syrup which was purified by chromatography on silica gel using dichloromethane-methanol 95:5 as eluent. Pure N-(9-Fluorenylmethyloxycarbonyl)-3-O-(2,3,4-tri-O-acetyl-β-L-fucopyrano syl)-L-serine (294 mg, 88%) was obtained as a white powder, Rf =0.40 (9:1, dichloromethane:methanol). 1H-NMR (CD3OD): ε 7.82-7.25 (m, 8 H, aromatic), 5.18 (m, 1 H, sec. order, H-4), 5.08-4.98 (m, 2 H, sec. order, H-2, 3), 4.50 (d, 1 H, J1,2 =7.5 Hz, H-1), 4.44-3.95 (complex, 6 H, Fmoc-H and serine H's), 3.83 (q, J5,6 =6.25 Hz, H-6), 2.11, 1.99 and 1.92 (each s, 3 H, Ac), 1.10 (d, 3 H, H-6). 13C: ε 102.6 (C-1), 72.5, 71.8 and 70.3 (C-2, 3 and 4), 71.5 and 67.9 (FMOC and serine CH2), 56.5 (serine CHN), 20.8, 20.5 and 20.4 (COCH3), 16.3 (C-6).

Workup

  1. customEvaporation and co-evaporation of the reaction mixture with toluene
  2. waitleft a syrup which
  3. customwas purified by chromatography on silica gel

Sources & evidence

ORD record
ord-133a519b18ef4ffb8f522ae248453e65
Source dataset
uspto-grants-1998_08
Patent number
US05795958

Reaction notes

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