Chloroform → HCID 131731860, compound

HRID 74847Notes

Reaction equation

HRID 74847 reaction equation
[C:1]([O:4][C@@H:5]1[C@@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@H:9]([O:15][C:16](=[O:18])[CH3:17])[C@@H:8]([CH2:19][O:20][C:21](=[O:23])[CH3:22])[O:7][C@@H:6]1[O:24][C@@H:25]1[C@@H:30]([CH2:31][O:32][C:33](=[O:35])[CH3:34])[O:29][C@H:28]([O:36][C@@H:37]2[C@@H:42]([CH2:43][O:44][C:45](=[O:47])[CH3:46])[O:41][C@@H:40]([N:48]=[N+:49]=[N-:50])[C@H:39]([O:51][C:52](=[O:54])[CH3:53])[C@H:38]2[O:55][C:56](=[O:58])[CH3:57])[C@H:27]([O:59][C:60](=[O:62])[CH3:61])[C@H:26]1[O:63][C:64](=[O:66])[CH3:65])(=[O:3])[CH3:2].[CH2:67]([O:70][CH:71]1[CH2:96][CH2:95][C@@:94]2([CH3:97])[CH:73]([CH2:74][CH2:75][C@@H:76]3[C@@H:93]2[CH2:92][CH2:91][C@@:90]2([CH3:98])[C@H:77]3[CH2:78][CH2:79][C@@H:80]2[C@H:81]([CH3:89])[CH2:82][CH2:83][CH2:84][CH:85]([CH3:88])[CH2:86]O)[CH2:72]1)[C:68]#[CH:69].C(Cl)(Cl)Cl.O=C1O[C@H]([C@H](CO)O)C([O-])=C1O.[Na+]>[O-]S([O-])(=O)=O.[Cu+2].CC(O)(C)C>[C:1]([O:4][C@@H:5]1[C@@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@H:9]([O:15][C:16](=[O:18])[CH3:17])[C@@H:8]([CH2:19][O:20][C:21](=[O:23])[CH3:22])[O:7][C@@H:6]1[O:24][C@@H:25]1[C@@H:30]([CH2:31][O:32][C:33](=[O:35])[CH3:34])[O:29][C@H:28]([O:36][C@@H:37]2[C@@H:42]([CH2:43][O:44][C:45](=[O:47])[CH3:46])[O:41][C@@H:40]([N:48]3[CH:69]=[C:68]([CH2:67][O:70][C@H:71]4[CH2:96][CH2:95][C@@:94]5([CH3:97])[CH:73]([CH2:74][CH2:75][C@@H:76]6[C@@H:93]5[CH2:92][CH2:91][C@@:90]5([CH3:98])[C@H:77]6[CH2:78][CH2:79][C@@H:80]5[C@H:81]([CH3:89])[CH2:82][CH2:83][CH2:84][CH:85]([CH3:86])[CH3:88])[CH2:72]4)[N:50]=[N:49]3)[C@H:39]([O:51][C:52](=[O:54])[CH3:53])[C@H:38]2[O:55][C:56](=[O:58])[CH3:57])[C@H:27]([O:59][C:60](=[O:62])[CH3:61])[C@H:26]1[O:63][C:64](=[O:66])[CH3:65])(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 6212ChloroformHCID 112053312,3,4,6-tetra-O-acetyl-alpha-D-glucopyranosyl-(1->4)-2,3,6-tri-O-acetyl-alpha-D-glucopyranosyl-(1->4)-2,3,6-tri-O-acetyl-beta-D-glucopyranosyl azideHCID 23667548Sodium AscorbateHCID 87398383HCID 87398383, compound

Product 1

HCID 131731860HCID 131731860, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 24462Copper SulfateCatalystHCID 6386tert-ButanolSolvent

Procedure

The azide 73 (200 mg, 211 μmol), 3-(prop-2-ynyloxy)cholestanol (3 equiv., 267 mg), CHCl3 (2 mL), t-BuOH (2 mL), CuSO4 (50 μL of a 0.3 M aqueous solution) and sodium ascorbate (62.5 μL of a 1M aqueous solution) was stirred vigorously overnight at r.t. The solvent was evaporated and the residue purified by column chromatography (SiO2: Hexane to 2:3 Hexane:EtOAc) to yield the triazole 74 (197 mg, 68%). 1H NMR (300 MHz, CDCl3) δ 7.66 (s, 1H, triazol-H), 5.85 (d, 1H, J1,2=9.3, H-1I), 5.46-5.27 (m, 6H, H-1II, H-1II, H-2I, H-4III, H-3II, H-3III), 5.03 (dd, 1H, J3,2=9.8, J3,4=9.8, H-3I), 4.82 (dd, 1H, J2,1=4.1, J2,3=10.3, H-2), 4.72 (dd, 1H, H-2), 4.63 (s, 2H, CH2O), 4.47-4.41 (m, 2H), 4.32-3.88 (m, 9H), 3.31 (m, 1H, CHO), 2.12 (s, 6H, OAc), 2.06 (s, 3H, OAc), 2.03 (s, 3H, OAc), 2.00 (s, 3H, OAc), 1.99 (s, 3H, OAc), 1.98 (s, 3H, OAc), 1.96 (s, 3H, OAc), 1.96-0.83 (m, 31H), 1.82 (s, 3H, OAc), 0.85 (d, 3H, J=6.7, CH3), 0.82 (m, 6H, CH3), 0.76 (s, 3H, CH3), 0.60 (s, 3H, CH3).

Workup

  1. customThe solvent was evaporated
  2. customthe residue purified by column chromatography (SiO2: Hexane to 2:3 Hexane:EtOAc)

Sources & evidence

ORD record
ord-505bdfe807db4be3922d3ca18e954880
Source dataset
uspto-grants-2014_09
Patent number
US08828952B2

Reaction notes

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