4-O-β-D-Mannopyranosyl-D-mannopyranose → HCID 131728631, compound

HRID 1359903Notes

Reaction equation

[CH2:1]([OH:23])[C@H:2]1[O:7][C@@H:6]([O:8][C@H:9]2[C@H:14]([OH:15])[C@H:13]([OH:16])[CH:12]([OH:17])[O:11][C@@H:10]2[CH2:18][OH:19])[C@@H:5]([OH:20])[C@@H:4]([OH:21])[C@@H:3]1[OH:22].[OH:24][CH:25]1[O:32][C@H:31]([CH2:33][OH:34])[C@@H:29]([OH:30])[C@H:27]([OH:28])[C@H:26]1[NH:35][C:36]([CH3:38])=[O:37]>C(Cl)Cl.C(S([O-])(=O)=O)(F)(F)F.[Ag+]>[OH:24][CH:25]1[O:32][C@H:31]([CH2:33][OH:34])[C@@H:29]([OH:30])[C@H:27]([OH:28])[C@H:26]1[NH:35][C:36]([CH3:38])=[O:37].[CH2:1]([OH:23])[C@H:2]1[O:7][C@@H:6]([O:8][C@H:9]2[C@H:14]([OH:15])[C@H:13]([OH:16])[CH:12]([OH:17])[O:11][C@@H:10]2[CH2:18][OH:19])[C@@H:5]([OH:20])[C@@H:4]([OH:21])[C@@H:3]1[OH:22]

Participants

Conditions

Temperature: -40 °C

Procedure

To a stirred mixture of Cp2HfCl2 (269.5 mg, 0.710 mmol), AgOTf (365.5 mg, 1.423 mmol), and molecular sieves 4A (3 g) in dry CH2Cl2 (5 mL) was added a solution of mannobiose acceptor (541.1 mg, 0.593 mmol) and GlcNAc-donor (354.0 g, 0.609 mmol) in dry CH2Cl2 (10 mL) at −78° C. The mixture was stirred for 2 h and at −40° C. for 1 h. Insoluble materials were removed by passage through silica gel and the filtrate was then diluted with EtOAc, washed with brine, aq. NaHCO3 and brine successively, dried over Na2SO4, and evaporated in vacuo. The residue was purified by silica gel column chromatography (toluene:EtOAc, 15:1-10:1) to afford compound GlcNAc-mannobiose donor (393.4 mg, 45%).

Workup

customInsoluble materials were removed by passage through silica gel
additionthe filtrate was then diluted with EtOAc
washwashed with brine, aq. NaHCO3 and brine successively
dry with materialdried over Na2SO4
customevaporated in vacuo
customThe residue was purified by silica gel column chromatography (toluene:EtOAc, 15:1-10:1)

Sources & evidence

ORD record: ord-4aca3e1e5bf648b3b5485d7056a8314a
Source dataset: uspto-grants-2011_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07879766B2

Reaction notes

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