Trifluoroacetic acid → (S)-2,5-dioxopyrrolidin-1-yl 5-[(2-{[alpha-D-mannopyranosyl-(1->3)-[alpha-D-mannopyranosyl-(1->6)]-alpha-D-mannopyranosyl]oxy}ethyl)amino]-5-oxo-2-[5-oxo-5-({2-[(alpha-L-fucopyranosyl)oxy]ethyl}amino)pentanamido]pentanoate

HRID 1488268Notes

Reaction equation

[C@H:1]1([O:12][C@H:13]2[C@H:18]([OH:19])[C@@H:17]([CH2:20][O:21][C@H:22]3[O:30][C@H:29]([CH2:31][OH:32])[C@@H:27]([OH:28])[C@H:25]([OH:26])[C@@H:23]3[OH:24])[O:16][C@H:15]([O:33][CH2:34][CH2:35][NH:36][C:37](=[O:66])[CH2:38][CH2:39][C@H:40]([NH:44][C:45](=[O:65])[CH2:46][CH2:47][CH2:48][C:49](=[O:64])[NH:50][CH2:51][CH2:52][O:53][C@@H:54]3[O:62][C@@H:61]([CH3:63])[C@@H:59]([OH:60])[C@@H:57]([OH:58])[C@@H:55]3[OH:56])[C:41]([OH:43])=[O:42])[C@H:14]2[OH:67])[O:9][C@H:8]([CH2:10][OH:11])[C@@H:6]([OH:7])[C@H:4]([OH:5])[C@@H:2]1[OH:3].[B-](F)(F)(F)F.CN(C(O[N:81]1[C:86](=[O:87])[CH2:85][CH2:84][C:82]1=[O:83])=[N+](C)C)C.CCN(C(C)C)C(C)C.C(O)(C(F)(F)F)=O.C(C#N)(C)=O>CN(C=O)C>[C@H:1]1([O:12][C@H:13]2[C@H:18]([OH:19])[C@@H:17]([CH2:20][O:21][C@H:22]3[O:30][C@H:29]([CH2:31][OH:32])[C@@H:27]([OH:28])[C@H:25]([OH:26])[C@@H:23]3[OH:24])[O:16][C@H:15]([O:33][CH2:34][CH2:35][NH:36][C:37](=[O:66])[CH2:38][CH2:39][C@H:40]([NH:44][C:45](=[O:65])[CH2:46][CH2:47][CH2:48][C:49](=[O:64])[NH:50][CH2:51][CH2:52][O:53][C@@H:54]3[O:62][C@@H:61]([CH3:63])[C@@H:59]([OH:60])[C@@H:57]([OH:58])[C@@H:55]3[OH:56])[C:41]([O:43][N:81]3[C:86](=[O:87])[CH2:85][CH2:84][C:82]3=[O:83])=[O:42])[C@H:14]2[OH:67])[O:9][C@H:8]([CH2:10][OH:11])[C@@H:6]([OH:7])[C@H:4]([OH:5])[C@@H:2]1[OH:3]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of (S)-5-[(2-{[α-D-mannopyranosyl-(1→3)-[α-D-mannopyranosyl-(1→6)]-α-D-mannopyranosyl]oxy}ethyl)amino]-5-oxo-2-[5-oxo-5-({2-[(α-L-fucopyranosyl)oxy]ethyl}amino)pentanamido]pentanoic acid (366 mg, 0.373 mmol) in DMF (2 mL) at 0° C. was added TSTU (115 mg, 0.381 mmol) and DIPEA (0.1 mL, 0.573 mmol). After stirring at 0° C. for 1 hour, the reaction was quenched with TFA (60 μL, 0.784 mmol). The reaction mixture was transferred dropwise, via autopipette, to a tube containing AcCN (45 mL). The resulting white suspension was centrifuged (3000 rpm, 15 minutes, at 4° C.) to generate a clear supernatant and a white pellet. The supernatant was discarded and the white pellet was washed with AcCN (1 mL) and dried to yield title compound UPLC Method B: calculated for C42H68N4O28 1076.40, observed m/e: 1077.28 [M+1]; Rt=0.90 min.

Workup

customThe reaction mixture was transferred dropwise, via autopipette, to a tube
custom(3000 rpm, 15 minutes, at 4° C.)
washthe white pellet was washed with AcCN (1 mL)
customdried

Sources & evidence

ORD record: ord-930b0f20ae6b428d849970363cd50324
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09427475B2

Reaction notes

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