(2R,3R)-2-(3,4-Dihydroxyphenyl)-3,4-dihydro-5,7-dihydroxy-2H-1-benzopyran-3-yl 4-hydroxybenzoate → HCID 69139781, compound

HRID 217539Notes

Reaction equation

HRID 217539 reaction equation
[OH:1][C:2]1[CH:30]=[CH:29][C:5]([C:6]([O:8][C@@H:9]2[CH2:18][C:17]3[C:12](=[CH:13][C:14]([OH:20])=[CH:15][C:16]=3[OH:19])[O:11][C@@H:10]2[C:21]2[CH:26]=[CH:25][C:24]([OH:27])=[C:23]([OH:28])[CH:22]=2)=[O:7])=[CH:4][CH:3]=1>C(Cl)(Cl)Cl>[C:6]([OH:8])(=[O:7])[CH3:5].[C:6]([OH:8])(=[O:7])[CH3:5].[C:6]([OH:8])(=[O:7])[CH3:5].[C:6]([OH:8])(=[O:7])[CH3:5].[C:6]([OH:8])(=[O:7])[CH3:5].[OH:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([O:8][C@@H:9]2[CH2:18][C:17]3[C:12](=[CH:13][C:14]([OH:20])=[CH:15][C:16]=3[OH:19])[O:11][C@@H:10]2[C:21]2[CH:26]=[CH:25][C:24]([OH:27])=[C:23]([OH:28])[CH:22]=2)=[O:7])=[CH:29][CH:30]=1

Participants

3

Reactant 1

HCID 10764037(2R,3R)-2-(3,4-Dihydroxyphenyl)-3,4-dihydro-5,7-dihydroxy-2H-1-benzopyran-3-yl 4-hydroxybenzoate

Product 1

HCID 69139781HCID 69139781, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Following the preparation procedure of 22*, the acetylation of 12 afforded 23* with 96% yield. mp 91-93° C.; [α]D=−26.5 (c=0.5, CHCl3); 1H NMR (CDCl3, 400 MHz): δ 7.89 (d, J=8.7 Hz, 2H), 7.37 (d, J=1.9 Hz, 1H), 7.34 (A of ABq, J=8.4, 1.9 Hz, 1H), 7.21 (B of AB, J=8.4 Hz, 1H), 7.10 (d, J=8.7 Hz, 2H), 6.74 (d, J=2.2 Hz, 1H), 6.59 (d, J=2.2 Hz, 1H), 5.64 (bs, 1H), 5.22 (bs, 1H), 3.11 (A of ABq, J=18.0, 4.5 Hz, 1H), 3.04 (B of ABq, J=18.0, 2.4 Hz, 1H), 2.29 (s, 3H), 2.28 (s, 6H), 2.26 (s, 3H), 2.25 (s, 3H); 13C NMR (CDCl3, 400 MHz): δ 168.8, 168.6, 168.3, 167.9, 167.8, 164.9, 154.9, 154.4, 149.7, 142.0, 141.8, 135.7, 131.3, 126.9, 124.2, 123.4, 121.7, 121.5, 109.5, 108.8, 108.0, 67.5, 26.0, 21.0, 20.7, 20.5; HRMS (ESI) calcd for C32H28O13Na (M+Na) 643.1428. found 643.1420.

Workup

  1. customthe preparation procedure of 22*

Sources & evidence

ORD record
ord-2c29405b730f44e88f1235a6eec92dfb
Source dataset
uspto-grants-2012_06
Patent number
US08193377B2

Reaction notes

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