Trifluoroacetic acid → 2-azidoethyl 2,4-di-O-benzoyl-3-O-(2,3,4,6-tetra-O-benzoyl-alpha-D-mannopyranosyl)-alpha-D-mannopyranoside

HRID 1488243Notes

Reaction equation

[C:1]([O:9][C@H:10]1[C@@H:21]([O:22][C@H:23]2[O:55][C@H:54]([CH2:56][O:57][C:58](=[O:65])[C:59]3[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=3)[C@@H:44]([O:45][C:46](=[O:53])[C:47]3[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=3)[C@H:34]([O:35][C:36](=[O:43])[C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)[C@@H:24]2[O:25][C:26](=[O:33])[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C@H:20]([O:66][C:67](=[O:74])[C:68]2[CH:73]=[CH:72][CH:71]=[CH:70][CH:69]=2)[C@@H:19]([CH2:75][O:76]C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[O:18][C@@H:11]1[O:12][CH2:13][CH2:14][N:15]=[N+:16]=[N-:17])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[C:1]([O:9][C@H:10]1[C@@H:21]([O:22][C@H:23]2[O:55][C@H:54]([CH2:56][O:57][C:58](=[O:65])[C:59]3[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=3)[C@@H:44]([O:45][C:46](=[O:53])[C:47]3[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=3)[C@H:34]([O:35][C:36](=[O:43])[C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)[C@@H:24]2[O:25][C:26](=[O:33])[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C@H:20]([O:66][C:67](=[O:74])[C:68]2[CH:73]=[CH:72][CH:71]=[CH:70][CH:69]=2)[C@@H:19]([CH2:75][OH:76])[O:18][C@@H:11]1[O:12][CH2:13][CH2:14][N:15]=[N+:16]=[N-:17])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 25 °C

Procedure

In a 50 mL round bottom flask was added 2-azidoethyl 2,4-di-O-benzoyl-3-O-(2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl)-6-O-trityl-α-D-mannopyranoside (450 mg, 0.352 mmol) and CH2Cl2 (3 mL). To the above solution was added TFA (3 mL, 38.9 mmol). After stirring at 25° C. for 1 hr, the reaction mixture was diluted with CH2Cl2 (10 mL), washed with water (3×15 mL) and brine (10 mL). The organic phase was dried over MgSO4, filtered and concentrated. The residue was purified by flash chromatography on silica gel (40 g), eluting with 0-100% EtOAc in hexanes, to give the title product. LC-MS Method A: m/e=1053.57 [M+18]; Rt=2.73 min. 1H NMR (CDCl3) δ 7.0-8.5 (m, 45H), 6.1 (t, 1H), 6.0 (t, 1H), 5.7 (m, 2H), 5.4 (s, 1H), 5.3 (s, 1H), 5.25 (s, 1H), 4.6 (m, 2H), 4.5 (m, 1H), 4.3 (m, 1H), 4.0-4.2 (m, 3h), 3.8 (m, 1H), 3.3-3.5 (m, 3H).

Workup

washwashed with water (3×15 mL) and brine (10 mL)
dry with materialThe organic phase was dried over MgSO4
filtrationfiltered
concentrationconcentrated
customThe residue was purified by flash chromatography on silica gel (40 g)
washeluting with 0-100% EtOAc in hexanes

Sources & evidence

ORD record: ord-50deb3b06669422eac4f4f498169e9f3
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09427475B2

Reaction notes

Loading…