HCID 69624790, compound → 2-alpha-D-Mannopyranosyl-L-tryptophan

HRID 397292Notes

Reaction equation

HRID 397292 reaction equation
C([NH:11][C@@H:12]([CH2:16][C:17]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[NH:19][C:18]=1[C@H:26]1[O:55][C@H:54]([CH2:56][O:57]CC2C=CC=CC=2)[C@@H:45]([O:46]CC2C=CC=CC=2)[C@H:36]([O:37]CC2C=CC=CC=2)[C@@H:27]1[O:28]CC1C=CC=CC=1)[C:13]([OH:15])=[O:14])(OCC1C=CC=CC=1)=O.[H][H]>C(O)C.[OH-].[Pd+2].[OH-].[C]>[NH2:11][C@@H:12]([CH2:16][C:17]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[NH:19][C:18]=1[C@H:26]1[O:55][C@H:54]([CH2:56][OH:57])[C@@H:45]([OH:46])[C@H:36]([OH:37])[C@@H:27]1[OH:28])[C:13]([OH:15])=[O:14]

Participants

5

Reactant 2

HCID 69624790HCID 69624790, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 109819702-alpha-D-Mannopyranosyl-L-tryptophanYield 62%

Reagents, catalysts & solvents 2

HCID 178502593HCID 178502593, compoundCatalystHCID 702EthanolSolvent

Procedure

To a solution of (2S*)-2-[N-(carbobenzyloxy)amino]-3-[2-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)indole-3-yl]propionic acid [compound (XII-2) wherein R1 to R4 are benzyl and Ar is phenyl](90.5 mg (0.11 mmol)) in ethanol (25 ml) was added 20% palladium hydroxide-carbon catalyst (75 mg) and the mixture was stirred at about 60° C. for about 11 hours under atmospheric pressure in the presence of hydrogen. The reacted solution was filtrated on Celite and the filtrate was concentrated. The residue was fractionated by high performance liquid chromatography [column: YMC-Pack ODS-AM SH-365-10AM, 500×30 mm, S-10, 120Å; temperature: room temperature; migrating layer: 5% acetonitrile-water; flow rate: 40 ml/min.; detection: 278 nm (UV)] and then freeze-dried to give 24 mg (yield 62%) of (2S*)-2-amino-3-[2-(α-D-mannopyranosyl)indole-3-yl]propionic acid [compound (XIII-2)].

Workup

  1. filtrationThe reacted solution was filtrated on Celite
  2. concentrationthe filtrate was concentrated
  3. customwas fractionated by high performance liquid chromatography [column: YMC-Pack ODS-AM SH-365-10AM, 500×30 mm, S-10, 120Å; temperature: room temperature; migrating layer: 5% acetonitrile-water; flow rate: 40 ml/min.; detection: 278 nm (UV)]
  4. customfreeze-dried

Sources & evidence

ORD record
ord-51cade9544f6414cbdba1f0f0592a4ff
Source dataset
uspto-grants-2003_08
Patent number
US06610502B1

Reaction notes

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