(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal → 1,2,3,4,6-Penta-O-(3,4,5-tri-O-benzylgalloyl)-b-D-glucopyranose

HRID 2271383Notes

Reaction equation

HRID 2271383 reaction equation
[O:1]=[CH:2][C@@H:3]([C@H:5]([C@@H:7]([C@@H:9]([CH2:11][OH:12])[OH:10])[OH:8])[OH:6])[OH:4].[CH2:13]([O:20][C:21]1[CH:22]=[C:23]([CH:27]=[C:28]([O:38][CH2:39][C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[C:29]=1[O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:24]([OH:26])=O)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.CCN=C=N[CH2:51][CH2:52][CH2:53]N(C)C.Cl>CN(C1C=CN=CC=1)C.C(Cl)Cl>[C:14]1([CH2:13][O:20][C:21]2[CH:22]=[C:23]([CH:27]=[C:28]([O:38][CH2:39][C:40]3[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=3)[C:29]=2[O:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:24]([O:1][C@@H:2]2[O:10][C@H:9]([CH2:11][O:12][C:24](=[O:26])[C:23]3[CH:22]=[C:21]([O:20][CH2:13][C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=4)[C:29]([O:30][CH2:31][C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)=[C:28]([O:38][CH2:39][C:51]4[CH:52]=[CH:53][CH:41]=[CH:40][CH:45]=4)[CH:27]=3)[C@@H:7]([O:8][C:24](=[O:26])[C:23]3[CH:27]=[C:28]([O:38][CH2:39][C:40]4[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=4)[C:29]([O:30][CH2:31][C:32]4[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=4)=[C:21]([O:20][CH2:13][C:14]4[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=4)[CH:22]=3)[C@H:5]([O:6][C:24](=[O:26])[C:23]3[CH:27]=[C:28]([O:38][CH2:39][C:40]4[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=4)[C:29]([O:30][CH2:31][C:32]4[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=4)=[C:21]([O:20][CH2:13][C:14]4[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=4)[CH:22]=3)[C@H:3]2[O:4][C:24](=[O:26])[C:23]2[CH:27]=[C:28]([O:38][CH2:39][C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)[C:29]([O:30][CH2:31][C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=3)=[C:21]([O:20][CH2:13][C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH:22]=2)=[O:26])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 3

HCID 107526(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanalHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 111339693,4,5-Tris(benzyloxy)benzoic Acid

Product 1

HCID 161536161,2,3,4,6-Penta-O-(3,4,5-tri-O-benzylgalloyl)-b-D-glucopyranoseYield 9.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 1.17 mmol of D-glucose, 8.57 mmol of 3,4,5-tribenzyloxybenzoic acid, 10.68 mmol of EDC.HCl and 9.84 mmol of DMAP was suspended in 130 mL of CH2Cl2 and was heated at reflux overnight. The cooled reaction mixture was then extracted with 1N HCl (3×), saturated NaHCO3 (2×), and brine (2×), the organic layer was dried over MgSO4, filtered, and concentrated. The resulting residue was purified by column chromatography over silica gel (75:24:1 CH2Cl2:toluene:ethyl acetate) to provide 0.253 g (9%) of product. 1H NMR (CDCl3, 400 MHz) δ 7.45-7.15 (m, 85H), 6.21 (d, J=8.0 Hz, 1H), 6.05 (t, J=10.0 Hz, 1H), 5.84 (dd, J=10.0, 8.0 Hz, 1H), 5.73 (t, J=10.0 Hz, 1H), 5.14-4.92 (m, 30H), 4.76 (m, 1H), 4.44 (m, 1H), 4.35 (m, 1H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. customThe cooled reaction mixture
  4. extractionwas then extracted with 1N HCl (3×), saturated NaHCO3 (2×), and brine (2×)
  5. dry with materialthe organic layer was dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe resulting residue was purified by column chromatography over silica gel (75:24:1 CH2Cl2:toluene:ethyl acetate)

Sources & evidence

ORD record
ord-b1d580565c834883979fdcd3d27fade8
Source dataset
uspto-grants-2015_09
Patent number
US09120744B2

Reaction notes

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