Potassium thiocyanate → HCID 131731862, compound

HRID 74858Notes

Reaction equation

HRID 74858 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](Br)[C@H:64]([O:79][C:80](=[O:87])[C:81]3[CH:86]=[CH:85][CH:84]=[CH:83][CH:82]=3)[C@H:63]2[O:88][C:89](=[O:96])[C:90]2[CH:95]=[CH:94][CH:93]=[CH:92][CH:91]=2)[C@H:47]([O:97][C:98](=[O:105])[C:99]2[CH:104]=[CH:103][CH:102]=[CH:101][CH:100]=2)[C@H:46]1[O:106][C:107](=[O:114])[C:108]1[CH:113]=[CH:112][CH:111]=[CH:110][CH:109]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:115]([S-:117])#[N:116].[K+]>[N+](CCCC)(CCCC)(CCCC)CCCC.[I-].C(#N)C>[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]([N:116]=[C:115]=[S:117])[C@H:64]([O:79][C:80](=[O:87])[C:81]3[CH:86]=[CH:85][CH:84]=[CH:83][CH:82]=3)[C@H:63]2[O:88][C:89](=[O:96])[C:90]2[CH:95]=[CH:94][CH:93]=[CH:92][CH:91]=2)[C@H:47]([O:97][C:98](=[O:105])[C:99]2[CH:104]=[CH:103][CH:102]=[CH:101][CH:100]=2)[C@H:46]1[O:106][C:107](=[O:114])[C:108]1[CH:113]=[CH:112][CH:111]=[CH:110][CH:109]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 516872Potassium thiocyanateHCID 161425652,3,4,6-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 bromide

Product 1

HCID 131731862HCID 131731862, compoundYield 64.7%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
75 °C

Procedure

Bromide 84 (1.8 g, 1.12 mmol), KSCN (3 equiv., 326 mg), molecular sieves and Bu4NI (cat.) were taken up in dry acetonitrile and stirred at 75° C. overnight. The solvent was evaporated and the residue taken up in DCM and washed with NaHCO3(sat.), before being dried (Na2SO4) and the solvent was evaporated. The crude product was purified using column chromatography (SiO2:Hexane to 35% EtOAc/Hexane, loaded with toluene) to yield 1.15 g of the white solid product (65%). 1H NMR (400 MHz, CDCl3) δ: 8.23-7.12 (m, 50H, Ar), 6.16 (dd, 1H, J3,2=9.6, J3,4=9.6, H-3III), 5.96 (dd, 1H, J3,2=9.6, J3,4=8.2, H-3II), 5.81 (d, 1H, J1,2=4.1, H-1III), 5.75-5.68 (m, 2H, H-3I, H-4III), 5.65 (d, 1H, J1,2=4.1, H-1II), 5.40 (dd, 1H, J2,1=8.2, J2,3=8.2, H-2I), 5.32 (dd, 1H, J2,1=4.1, J2,3=10.2, H-2III), 5.28 (d, 1H, J1,2=8.2, H-1I), 5.13 (dd, 1H, J2,1=4.1, J2,3=10.2, H-2II), 5.00 (dd, 1H, H-6I), 4.77 (dd, 1H, H-6II), 4.72-4.65 (m, 2H, H-6I, H-6II), 4.53-4.41 (m, 5H, H-5II, H-5III, H-4I, H-1II, H-6III), 4.30 (dd, 1H, H-6III), 4.13 (ddd, 1H, H-5I).

Workup

  1. customThe solvent was evaporated
  2. washwashed with NaHCO3(sat.)
  3. dry with materialbefore being dried (Na2SO4)
  4. customthe solvent was evaporated
  5. customThe crude product was purified

Sources & evidence

ORD record
ord-85b96dd68e0d44ec9520da90d1db0df2
Source dataset
uspto-grants-2014_09
Patent number
US08828952B2

Reaction notes

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