Benzyl 2,3,4,6-tetra-O-benzoyl-alpha-D-mannopyranosyl-(1->2)-3,4,6-tri-O-benzoyl-alpha-D-mannopyranoside → HCID 86658272, compound

HRID 74834Notes

Reaction equation

HRID 74834 reaction equation
[C:1]([O:9][C@H:10]1[C@@H:15]([O:16][C:17](=[O:24])[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C@H:14]([O:25][C:26](=[O:33])[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C@@H:13]([CH2:34][O:35][C:36](=[O:43])[C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[O:12][C@@H:11]1[O:44][C@H:45]1[C@@H:58]([O:59][C:60](=[O:67])[C:61]2[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=2)[C@H:57]([O:68][C:69](=[O:76])[C:70]2[CH:75]=[CH:74][CH:73]=[CH:72][CH:71]=2)[C@@H:56]([CH2:77][O:78][C:79](=[O:86])[C:80]2[CH:85]=[CH:84][CH:83]=[CH:82][CH:81]=2)[O:55][C@@H:46]1[O:47]CC1C=CC=CC=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H][H]>CO.CCOC(C)=O.[Pd]>[C:1]([O:9][C@H:10]1[C@@H:15]([O:16][C:17](=[O:24])[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C@H:14]([O:25][C:26](=[O:33])[C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[C@@H:13]([CH2:34][O:35][C:36](=[O:43])[C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[O:12][C@@H:11]1[O:44][C@H:45]1[C@@H:58]([O:59][C:60](=[O:67])[C:61]2[CH:62]=[CH:63][CH:64]=[CH:65][CH:66]=2)[C@H:57]([O:68][C:69](=[O:76])[C:70]2[CH:71]=[CH:72][CH:73]=[CH:74][CH:75]=2)[C@@H:56]([CH2:77][O:78][C:79](=[O:86])[C:80]2[CH:81]=[CH:82][CH:83]=[CH:84][CH:85]=2)[O:55][CH:46]1[OH:47])(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 2

HCID 86658273Benzyl 2,3,4,6-tetra-O-benzoyl-alpha-D-mannopyranosyl-(1->2)-3,4,6-tri-O-benzoyl-alpha-D-mannopyranosideHCID 178418361HCID 178418361, compound

Product 1

HCID 86658272HCID 86658272, compoundYield 99%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalyst2×HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

The disaccharide 28 (670 mg, 0.577 mmol) was dissolved in MeOH (3 mL) and EtOAc (30 mL). Palladium on charcoal (5%, 80 mg) was added. The mixture was stirred under 50 psi of hydrogen at r.t. o/n. TLC indicated ˜60% conversion. More palladium on charcoal (5%, 80 mg) was added. Stirring was continued at 50 psi for 3 days. TLC indicated complete conversion. The mixture was filtered through a plug of Celite and rinsed with EtOAc (5×1 mL). The combined filtrate and washings were evaporated to dryness to give the title compound 29 as a colourless foam (609 mg, 99%). The product was used directly for the next step without purification.

Workup

  1. filtrationThe mixture was filtered through a plug of Celite
  2. washrinsed with EtOAc (5×1 mL)
  3. customThe combined filtrate and washings were evaporated to dryness

Sources & evidence

ORD record
ord-e7c3c3425c5c4050960326d8b50a9a5d
Source dataset
uspto-grants-2014_09
Patent number
US08828952B2

Reaction notes

Loading…