Vanillic Acid → HCID 67607156, compound

HRID 1024325Notes

Reaction equation

HRID 1024325 reaction equation
[C:1](O)(=O)[C:2]1[CH:10]=[CH:9][C:7]([OH:8])=[C:4]([O:5][CH3:6])[CH:3]=1.C([C@:20]([C@:24](CC1C=CC=CC=1)([C@@:26](CC1C=CC=CC=1)([C@@H:28]([CH:30](CC1C=CC=CC=1)[OH:31])[OH:29])[OH:27])[OH:25])([OH:23])[CH:21]=[O:22])C1C=CC=CC=1.Cl.C(N=C=NCCCN(C)C)C.C(N(CC)CC)C>CN(C=O)C.CN(C)C1C=CN=CC=1>[CH2:1]([C:21]([C@@H:20]([C@H:24]([C@@H:26]([C@@H:28]([CH2:30][OH:31])[OH:29])[OH:27])[OH:25])[OH:23])=[O:22])[C:2]1[CH:10]=[CH:9][C:7]([OH:8])=[C:4]([O:5][CH3:6])[CH:3]=1

Participants

7

Reactant 4

HCID 8468Vanillic AcidHCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 54134955HCID 54134955, compound

Product 1

HCID 67607156HCID 67607156, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

Vanillic acid having a benzyl-protected hydroxyl group at the 4 position and 2,3,4,6-tetrabenzyl glucose having benzyl-protected hydroxyl groups at positions other than the 1 position (Sigma-Aldrich) were condensed in a DMF solvent (at a reaction temperature of 60° C.) using the following condensing agents: 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride (EDCI, Kokusaikagaku Co., Ltd.), 4-dimethylaminopyridine (DMAP, Tokyo Kasei Kogyo), and triethylamine (Et3N, Wako Pure Chemical Industries, Ltd.). The obtained condensate was a mixture comprising a anomer and β anomer at a ratio of 1:2. The condensate was purified using an open column (at different concentration ratios of hexane:ethyl acetate=6:1 and 5:1). A unreacted starting material was removed. The yield was found to be 84%: Molecular MS [M+Na]+ m/z 803.14, 1H NMR (300 MHz, CDCl3): δ7.60 (1H, dd, H-6), 7.59 (1H, d, H-2), 7.45-7.26 (60H, m, H-benzylic CH2), 6.90 (1H, d, H-5), 6.55 (1H, d, H-Glc1α, J=3.21), 5.84 (1H, d, H-Glc1β, J=7.65), 5.25 (10H, s, H-benzylic CH2), 4.96-3.56 (94H, m, CH3, H-Glc).

Workup

  1. customthe following condensing agents
  2. customThe condensate was purified
  3. concentrationan open column (at different concentration ratios of hexane:ethyl acetate=6:1 and 5:1)
  4. customwas removed

Sources & evidence

ORD record
ord-2427a8d84dbe4ef2a2c95a462948e70e
Source dataset
uspto-grants-2014_05
Patent number
US08722868B2

Reaction notes

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