D-Psicose → HCID 118005708, compound

HRID 1488263Notes

Reaction equation

HRID 1488263 reaction equation
[O:1]=[C:2]([NH:39][CH2:40][CH2:41][O:42][C@@H:43]1[O:51][C@@H:50]([CH3:52])[C@@H:48]([OH:49])[C@@H:46]([OH:47])[C@@H:44]1[OH:45])[C@@H:3]([NH:22][CH:23]([CH2:34][CH2:35][CH2:36][CH:37]=[O:38])[C:24]([O:26]CC1C=CC=CC=1)=[O:25])[CH2:4][CH2:5][C:6](=[O:21])[NH:7][CH2:8][CH2:9][O:10][C@@H:11]1[O:19][C@@H:18]([CH3:20])[C@@H:16]([OH:17])[C@@H:14]([OH:15])[C@@H:12]1[OH:13].OCC1(OC[C@@H](O)[C@@H](O)[C@H]1O)O>[OH-].[OH-].[Pd+2].CO>[O:1]=[C:2]([NH:39][CH2:40][CH2:41][O:42][C@@H:43]1[O:51][C@@H:50]([CH3:52])[C@@H:48]([OH:49])[C@@H:46]([OH:47])[C@@H:44]1[OH:45])[C@@H:3]([NH:22][CH:23]([CH2:34][CH2:35][CH2:36][CH:37]=[O:38])[C:24]([OH:26])=[O:25])[CH2:4][CH2:5][C:6](=[O:21])[NH:7][CH2:8][CH2:9][O:10][C@@H:11]1[O:19][C@@H:18]([CH3:20])[C@@H:16]([OH:17])[C@@H:14]([OH:15])[C@@H:12]1[OH:13]

Participants

5

Reactant 2

HCID 441036D-PsicoseHCID 131736858HCID 131736858, compound

Product 1

HCID 118005708HCID 118005708, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

A suspension of benzyl {[(2S)-1,5-dioxo-1,5-bis({2-[(α-L-fucopyranosyl)oxy]ethyl}amino)pentan-2-yl]amino}-6-oxohexanoate (380 mg, 0.511 mmol) and Pearlman's catalyst (50 mg, 0.071 mmol) in methanol (30 mL) was agitated under 50 Psi of H2 at room temperature on a Parr shaker. After 16 hours, catalyst was filtered off and the filtrate was concentrated to give the title compound. 1H NMR (CD3OD) δ 4.76-4.75 (m, 2H), 4.32-4.29 (m, 1H), 3.96-3.91 (m, 2H), 3.76-3.66 (m, 5H), 3.55-3.27 (m, 9H), 2.34-2.27 (m, 6H), 2.09-2.04 (m, 1H), 1.99-1.88 (m, 1H), 1.67-1.61 (m, 4H), 1.20 (d, J=6.7, 6H).

Workup

  1. filtrationcatalyst was filtered off
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-ae6e4d6d80144e4691cc53abf851623d
Source dataset
uspto-grants-2016_08
Patent number
US09427475B2

Reaction notes

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