Reaction SMILES: [Na:1].[Na].[Na].[Na].[Na].[Na].[Na].[Na].[Na].[Na].[Na].[Na].[Na].[Na].[CH2:15]([C@@:22]1([O:38][C@H:37]([CH2:39][NH:40][C:41]([C@@H:43]([C@H:49]([C@@H:55]([C@@H:61]([CH2:67][O:68][S:69]([OH:72])(=[O:71])=[O:70])[O:62][S:63]([OH:66])(=[O:65])=[O:64])[O:56][S:57]([OH:60])(=[O:59])=[O:58])OS(O)(=O)=O)[O:44][S:45]([OH:48])(=[O:47])=[O:46])=[O:42])[C@@H:31]([O:32][S:33]([OH:36])(=[O:35])=[O:34])[C@H:25]([O:26][S:27]([OH:30])(=[O:29])=[O:28])[C@H:24]1[NH:73][C:74]([C:76]1[CH:81]=[CH:80][C:79]([C:82]2[CH:87]=[CH:86][C:85]([C:88]([NH:90][C@@H:91]3[C@@H:97]([O:98][S:99]([OH:102])(=[O:101])=[O:100])[C@H:96]([O:103][S:104]([OH:107])(=[O:106])=[O:105])[C@@H:95]([CH2:108][NH:109][C:110]([C@@H:112]([C@H:118]([C@@H:124]([C@@H:130]([CH2:136][O:137][S:138]([OH:141])(=[O:140])=[O:139])[O:131][S:132]([OH:135])(=[O:134])=[O:133])[O:125][S:126]([OH:129])(=[O:128])=[O:127])OS(O)(=O)=O)[O:113][S:114]([OH:117])(=[O:116])=[O:115])=[O:111])[O:94][C@:92]3([CH2:142][C:143]3[CH:148]=[CH:147][CH:146]=[CH:145][CH:144]=3)[OH:93])=[O:89])=[CH:84][CH:83]=2)=[CH:78][CH:77]=1)=[O:75])[OH:23])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>[OH-].[Na+]>[Na:1].[Na:1].[Na:1].[Na:1].[Na:1].[Na:1].[Na:1].[Na:1].[Na:1].[Na:1].[Na:1].[Na:1].[CH2:15]([C@@:22]1([O:38][C@H:37]([CH2:39][NH:40][C:41](/[C:43](=[CH:49]/[C@@H:55]([C@@H:61]([CH2:67][O:68][S:69]([OH:72])(=[O:70])=[O:71])[O:62][S:63]([OH:66])(=[O:65])=[O:64])[O:56][S:57]([OH:60])(=[O:59])=[O:58])/[O:44][S:45]([OH:48])(=[O:47])=[O:46])=[O:42])[C@@H:31]([O:32][S:33]([OH:36])(=[O:34])=[O:35])[C@H:25]([O:26][S:27]([OH:30])(=[O:28])=[O:29])[C@H:24]1[NH:73][C:74]([C:76]1[CH:81]=[CH:80][C:79]([C:82]2[CH:83]=[CH:84][C:85]([C:88]([NH:90][C@@H:91]3[C@@H:97]([O:98][S:99]([OH:102])(=[O:101])=[O:100])[C@H:96]([O:103][S:104]([OH:107])(=[O:105])=[O:106])[C@@H:95]([CH2:108][NH:109][C:110](/[C:112](=[CH:118]/[C@@H:124]([C@@H:130]([CH2:136][O:137][S:138]([OH:141])(=[O:140])=[O:139])[O:131][S:132]([OH:135])(=[O:133])=[O:134])[O:125][S:126]([OH:129])(=[O:128])=[O:127])/[O:113][S:114]([OH:117])(=[O:115])=[O:116])=[O:111])[O:94][C@:92]3([CH2:142][C:143]3[CH:148]=[CH:147][CH:146]=[CH:145][CH:144]=3)[OH:93])=[O:89])=[CH:86][CH:87]=2)=[CH:78][CH:77]=1)=[O:75])[OH:23])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1
Reactant: O=C(N[C@@H]1[C@@H](OS(=O)(=O)O)[C@H](OS(=O)(=O)O)[C@@H](CNC(=O)[C@H](OS(=O)(=O)O)[C@@H](OS(=O)(=O)O)[C@H](OS(=O)(=O)O)[C@@H](COS(=O)(=O)O)OS(=O)(=O)O)O[C@@]1(O)Cc1ccccc1)c1ccc(-c2ccc(C(=O)N[C@@H]3[C@@H](OS(=O)(=O)O)[C@H](OS(=O)(=O)O)[C@@H](CNC(=O)[C@H](OS(=O)(=O)O)[C@@H](OS(=O)(=O)O)[C@H](OS(=O)(=O)O)[C@@H](COS(=O)(=O)O)OS(=O)(=O)O)O[C@@]3(O)Cc3ccccc3)cc2)cc1
Agent: [Na+]
Agent: [Na]
Agent: [OH-]
Product: O=C(NC[C@H]1O[C@@](O)(Cc2ccccc2)[C@H](NC(=O)c2ccc(-c3ccc(C(=O)N[C@@H]4[C@@H](OS(=O)(=O)O)[C@H](OS(=O)(=O)O)[C@@H](CNC(=O)/C(=C/[C@H](OS(=O)(=O)O)[C@@H](COS(=O)(=O)O)OS(=O)(=O)O)OS(=O)(=O)O)O[C@@]4(O)Cc4ccccc4)cc3)cc2)[C@@H](OS(=O)(=O)O)[C@@H]1OS(=O)(=O)O)/C(=C/[C@H](OS(=O)(=O)O)[C@@H](COS(=O)(=O)O)OS(=O)(=O)O)OS(=O)(=O)O

Procedure:
A solution of 200 mg of biphenyl-4,4'-dicarboxylic acid bis-[[benzyl 2,6-didesoxy-3,4-di-O-sulfo-6-(2,3,4,5,6-penta-O-sulfo-D-gluconoylamino)-α-D-glucopyranosid-2-yl]-amide] tetradecasodium salt (see Ex. 14.F.) in 12 ml of 2N sodium hydroxide was left at room temperature for 8 hours, neutralized with acidic ion exchanger (Amberlite IR 120 H+) and concentrated. The residue was chromatographed over Sephadex C25 Na+) with water and gave biphenyl-4,4'-dicarboxylic acid bis-[[(Z)-benzyl 2,6-didesoxy-3,4-di-O-sulfo-6-(3-desoxy-2,4,5,6-tetra-O-sulfo-D-erythro-hex-2-enonoylamino)-α-D-glucopyranosid-2-yl]-amide] dodecasodium salt, [α]+67.50 (c 0.2; water), MS: m/z 2288 (reconstructed M).