Toluene → 2,3,4,6-tetra-O-benzoyl-alpha-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzoyl-alpha-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzoyl-alpha-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzoyl-beta-D-glucopyranosylamine

HRID 74848Notes

Reaction equation

HRID 74848 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]([CH2:51][O:52][C:53](=[O:60])[C:54]2[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=2)[O:49][C@H:48]([O:61][C@@H:62]2[C@@H:67]([CH2:68][O:69][C:70](=[O:77])[C:71]3[CH:76]=[CH:75][CH:74]=[CH:73][CH:72]=3)[O:66][C@H:65]([O:78][C@@H:79]3[C@@H:84]([CH2:85][O:86][C:87](=[O:94])[C:88]4[CH:93]=[CH:92][CH:91]=[CH:90][CH:89]=4)[O:83][C@@H:82]([N:95]=[N+]=[N-])[C@H:81]([O:98][C:99](=[O:106])[C:100]4[CH:105]=[CH:104][CH:103]=[CH:102][CH:101]=4)[C@H:80]3[O:107][C:108](=[O:115])[C:109]3[CH:114]=[CH:113][CH:112]=[CH:111][CH:110]=3)[C@H:64]([O:116][C:117](=[O:124])[C:118]3[CH:123]=[CH:122][CH:121]=[CH:120][CH:119]=3)[C@H:63]2[O:125][C:126](=[O:133])[C:127]2[CH:132]=[CH:131][CH:130]=[CH:129][CH:128]=2)[C@H:47]([O:134][C:135](=[O:142])[C:136]2[CH:141]=[CH:140][CH:139]=[CH:138][CH:137]=2)[C@H:46]1[O:143][C:144](=[O:151])[C:145]1[CH:150]=[CH:149][CH:148]=[CH:147][CH:146]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(C)C=CC=CC=1>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: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]([CH2:51][O:52][C:53](=[O:60])[C:54]2[CH:55]=[CH:56][CH:57]=[CH:58][CH:59]=2)[O:49][C@H:48]([O:61][C@@H:62]2[C@@H:67]([CH2:68][O:69][C:70](=[O:77])[C:71]3[CH:76]=[CH:75][CH:74]=[CH:73][CH:72]=3)[O:66][C@H:65]([O:78][C@@H:79]3[C@@H:84]([CH2:85][O:86][C:87](=[O:94])[C:88]4[CH:93]=[CH:92][CH:91]=[CH:90][CH:89]=4)[O:83][C@@H:82]([NH2:95])[C@H:81]([O:98][C:99](=[O:106])[C:100]4[CH:101]=[CH:102][CH:103]=[CH:104][CH:105]=4)[C@H:80]3[O:107][C:108](=[O:115])[C:109]3[CH:110]=[CH:111][CH:112]=[CH:113][CH:114]=3)[C@H:64]([O:116][C:117](=[O:124])[C:118]3[CH:123]=[CH:122][CH:121]=[CH:120][CH:119]=3)[C@H:63]2[O:125][C:126](=[O:133])[C:127]2[CH:132]=[CH:131][CH:130]=[CH:129][CH:128]=2)[C@H:47]([O:134][C:135](=[O:142])[C:136]2[CH:141]=[CH:140][CH:139]=[CH:138][CH:137]=2)[C@H:46]1[O:143][C:144](=[O:151])[C:145]1[CH:150]=[CH:149][CH:148]=[CH:147][CH:146]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 1140TolueneHCID 86658285HCID 86658285, compound

Product 1

HCID 866582842,3,4,6-tetra-O-benzoyl-alpha-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzoyl-alpha-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzoyl-alpha-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzoyl-beta-D-glucopyranosylamineYield 101.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent2×

Procedure

The azide 67 (201 mg, 0.098 mmol) was dissolved in EtOAc (10 mL) and stirred with Pd—C (10%, (w/w), 100 mg) under H2 atmosphere for 3 h (TLC: toluene:EtOAc, 7:1). H2 was replaced by Ar then the mixture was filtered through celite (prewashed with MeOH and EtOAc, 5 mL), washed with EtOAc (5×20 mL, +sonication) and finally concentrated in vacuo at r.t. to obtain the amine 80 as a white solid (200 mg, 100%), used without further purification or characterization in the next step.

Workup

  1. filtrationthe mixture was filtered through celite (prewashed with MeOH and EtOAc, 5 mL)
  2. washwashed with EtOAc (5×20 mL, +sonication)
  3. concentrationfinally concentrated in vacuo at r.t.

Sources & evidence

ORD record
ord-cae11e27adf145719d9492166e46cef5
Source dataset
uspto-grants-2014_09
Patent number
US08828952B2

Reaction notes

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