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Mannobiose → HCID 131728631, compound

HRID 1359903
Notes
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Reaction equation

HRID 1359903 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 152109MannobioseHCID 439174N-Acetyl-D-Glucosamine

Product 1

HCID 131728631HCID 131728631, compound

Reagents, catalysts & solvents 2

HCID 76223Silver(I) trifluoromethanesulfonateCatalystHCID 6344DichloromethaneSolvent2×

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

  1. customInsoluble materials were removed by passage through silica gel
  2. additionthe filtrate was then diluted with EtOAc
  3. washwashed with brine, aq. NaHCO3 and brine successively
  4. dry with materialdried over Na2SO4
  5. customevaporated in vacuo
  6. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes