HCID 86658277, compound → 2,3,4,6-tetra-O-benzoyl-alpha-D-mannopyranosyl-(1->3)-2,4,6-tri-O-benzoyl-alpha-D-mannopyranosyl-(1->3)-2,4,6-tri-O-benzoyl-D-mannopyranose

HRID 74840Notes

Reaction equation

HRID 74840 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:50]([O:51][C:52](=[O:59])[C:53]2[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=2)[C@@H:49]([CH2:60][O:61][C:62](=[O:69])[C:63]2[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=2)[O:48][C@H:47]([O:70][C@H:71]2[C@H:84]([O:85][C:86](=[O:93])[C:87]3[CH:92]=[CH:91][CH:90]=[CH:89][CH:88]=3)[C@@H:83]([CH2:94][O:95][C:96](=[O:103])[C:97]3[CH:102]=[CH:101][CH:100]=[CH:99][CH:98]=3)[O:82][C@H:73]([O:74]CC3C=CC=CC=3)[C@H:72]2[O:104][C:105](=[O:112])[C:106]2[CH:111]=[CH:110][CH:109]=[CH:108][CH:107]=2)[C@H:46]1[O:113][C:114](=[O:121])[C:115]1[CH:120]=[CH:119][CH:118]=[CH:117][CH:116]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CO.C(Cl)(Cl)Cl.[Pd]>[C:1]([O:9][C@H:10]1[C@@H:15]([O:16][C:17](=[O:24])[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=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:38]=[CH:39][CH:40]=[CH:41][CH:42]=2)[O:12][C@@H:11]1[O:44][C@H:45]1[C@H:50]([O:51][C:52](=[O:59])[C:53]2[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=2)[C@@H:49]([CH2:60][O:61][C:62](=[O:69])[C:63]2[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=2)[O:48][C@H:47]([O:70][C@H:71]2[C@H:84]([O:85][C:86](=[O:93])[C:87]3[CH:88]=[CH:89][CH:90]=[CH:91][CH:92]=3)[C@@H:83]([CH2:94][O:95][C:96](=[O:103])[C:97]3[CH:102]=[CH:101][CH:100]=[CH:99][CH:98]=3)[O:82][CH:73]([OH:74])[C@H:72]2[O:104][C:105](=[O:112])[C:106]2[CH:107]=[CH:108][CH:109]=[CH:110][CH:111]=2)[C@H:46]1[O:113][C:114](=[O:121])[C:115]1[CH:120]=[CH:119][CH:118]=[CH:117][CH:116]=1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 1

HCID 86658277HCID 86658277, compound

Product 1

HCID 866582782,3,4,6-tetra-O-benzoyl-alpha-D-mannopyranosyl-(1->3)-2,4,6-tri-O-benzoyl-alpha-D-mannopyranosyl-(1->3)-2,4,6-tri-O-benzoyl-D-mannopyranoseYield 93.1%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 6212ChloroformSolvent

Procedure

The benzyl glycoside 51 (385 mg, 0.235 mmol) was dissolved in MeOH (5 mL) and chloroform (5 mL). Palladium on charcoal (5%, 538 mg) was added. The mixture was stirred under hydrogen at 100 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, co-evaporated with DCM (3 mL) to give the hemiacetal 52 as pale-yellow foam (338 mg, 93%), used without further purification or characterization in the next step.

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, co-evaporated with DCM (3 mL)

Sources & evidence

ORD record
ord-b143425a69b744d9a53788ecf131fd5b
Source dataset
uspto-grants-2014_09
Patent number
US08828952B2

Reaction notes

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