2,3,4-Tri-O-acetyl-alpha-D-glucuronic Acid Methyl Ester → methyl 2,3,4-tri-O-acetyl-1-O-[p-[(E)-2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)-propenyl]-benzoyl]-D-glucopyranuronate

HRID 1447498Notes

Reaction equation

HRID 1447498 reaction equation
[C:1]([O:4][C@@H:5]1[C@@H:11]([O:12][C:13](=[O:15])[CH3:14])[C@H:10]([O:16][C:17](=[O:19])[CH3:18])[C@@H:9]([C:20]([O:22][CH3:23])=[O:21])[O:8][C@@H:6]1[OH:7])(=[O:3])[CH3:2].[CH3:24][C:25]1([CH3:49])[CH2:34][CH2:33][C:32]([CH3:36])([CH3:35])[C:31]2[CH:30]=[C:29](/[C:37](/[CH3:48])=[CH:38]/[C:39]3[CH:47]=[CH:46][C:42]([C:43](Cl)=[O:44])=[CH:41][CH:40]=3)[CH:28]=[CH:27][C:26]1=2>N1C=CC=CC=1.CCOCC>[C:1]([O:4][C@@H:5]1[C@@H:11]([O:12][C:13](=[O:15])[CH3:14])[C@H:10]([O:16][C:17](=[O:19])[CH3:18])[C@@H:9]([C:20]([O:22][CH3:23])=[O:21])[O:8][CH:6]1[O:7][C:43](=[O:44])[C:42]1[CH:46]=[CH:47][C:39](/[CH:38]=[C:37](/[C:29]2[CH:28]=[CH:27][C:26]3[C:25]([CH3:49])([CH3:24])[CH2:34][CH2:33][C:32]([CH3:36])([CH3:35])[C:31]=3[CH:30]=2)\[CH3:48])=[CH:40][CH:41]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 104046212,3,4-Tri-O-acetyl-alpha-D-glucuronic Acid Methyl EsterHCID 12836534p-[(E)-2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)-propenyl]-benzoyl chloride

Product 1

HCID 70546855methyl 2,3,4-tri-O-acetyl-1-O-[p-[(E)-2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)-propenyl]-benzoyl]-D-glucopyranuronate

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of 3.4 g of methyl 2,3,4-tri-O-acetyl-α-D-glucopyranuronate in 40 ml of pyridine was reacted at 0° C. with a solution of p-[(E)-2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)-propenyl]-benzoyl chloride in 70 ml of ether. The mixture was stirred at room temperature overnight, evaporated to dryness and the residue was chromatographed on silica gel with hexane/ethyl acetate. There was obtained methyl 2,3,4-tri-O-acetyl-1-O-[p-[(E)-2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)-propenyl]-benzoyl]-D-glucopyranuronate as a mixture of the β- and α-anomers (ca 4:1). Melting point 149°-150° C. (from ethanol); [α]D25 =3° (c=1 in chloroform).

Workup

  1. customevaporated to dryness
  2. customthe residue was chromatographed on silica gel with hexane/ethyl acetate

Sources & evidence

ORD record
ord-251d706527fc42d3b87ee2fc52fc72b1
Source dataset
uspto-grants-1982_02
Patent number
US04316983

Reaction notes

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