HCID 86753223, compound → HCID 86753222, compound

HRID 1940456Notes

Reaction equation

HRID 1940456 reaction equation
[CH2:1]([C:4]([C@@H:6]([C@H:8]([C@H:19]([C@@H:21]([CH2:23][OH:24])[OH:22])[OH:20])[O:9][CH:10](OC(C)(C)C)[C:11]([OH:13])=[O:12])[OH:7])=[O:5])[CH:2]=[CH2:3]>[OH-].[Na+]>[CH2:1]([C:4]([C@@H:6]([C@H:8]([C@H:19]([C@@H:21]([CH2:23][OH:24])[OH:22])[OH:20])[O:9][CH2:10][C:11]([OH:13])=[O:12])[OH:7])=[O:5])[CH:2]=[CH2:3]

Participants

3

Reactant 1

HCID 86753223HCID 86753223, compound

Product 1

HCID 86753222HCID 86753222, compoundYield 113%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

Compound 7 (7.8 g) was dissolved in 2N NaOH solution and stirred for 2 hr. The reaction mixture was acidified with Dowex-H resin and the resin was removed by filtration. The filtrate was lyophilized to give 1-C-allyl-3-O-carboxymethylgalactose (7.0 g). 1H NMR (CD3OD): δ, 2.38-2.42, 2H; 3.28-3.31, m, 1H; 3.44-3.47, dd, 2H; 3.63-3.67,m, 2H; 3.98-4.02, m, 1H; 4.11-4.15,m, 1H; 4.22-4.25,m, 1H; 4.95-5.00, and 5.10-5.15,dd, 2H, CH2CH=CH2 ; 5.75-5.85, m, 1H, CH2 CH=CH2 : 13C NMR (CD3OD): 176.52 (COOH); 136.67, 116.89, 81.98, 79.79, 76.00, 73.50, 68.60, 68.56, 67.59, 62.05, 30.70: [α]D =+66.82 (C 0.214, methanol).

Workup

  1. customthe resin was removed by filtration

Sources & evidence

ORD record
ord-332ce2daf237445393cde95d8714a172
Source dataset
uspto-grants-1997_12
Patent number
US05700458

Reaction notes

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