HCID 15932587, compound → HCID 54227580, compound

HRID 1656866Notes

Reaction equation

HRID 1656866 reaction equation
[C:1]([NH:4][C@@H:5]1[C@@H:10]([OH:11])[C@H:9]([OH:12])[C@@H:8]([CH2:13][OH:14])[O:7][C@H:6]1[O:15][C@H:16]1[C@@H:31]([CH2:32][O:33][C@@H:34]2[O:41][C@H:40]([CH2:42][OH:43])[C@@H:38]([OH:39])[C@H:36]([OH:37])[C@H:35]2[NH:44][C:45](=[O:47])[CH3:46])[O:30][C@@H:19]([O:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26]([O:28][CH3:29])=[O:27])[C@H:18]([OH:48])[C@H:17]1[OH:49])(=[O:3])[CH3:2].C1C(=O)NC(=O)NC=1[C@@H]1O[C@H](COP(OP(O[C@H:73]2[O:78][C@H:77]([CH2:79][OH:80])[C@H:76]([OH:81])[C@H:75]([OH:82])[C@H:74]2[OH:83])(O)=O)(O)=O)[C@@H](O)[C@H]1O>[As](C)(C)(=O)[O-].[Na+].[Cl-].[Mn+2].[Cl-]>[C@@H:19]1([O:12][C@@H:9]2[C@@H:8]([CH2:13][OH:14])[O:7][C@@H:6]([O:15][C@H:16]3[C@@H:31]([CH2:32][O:33][C@@H:34]4[O:41][C@H:40]([CH2:42][OH:43])[C@@H:38]([O:39][C@@H:73]5[O:78][C@H:77]([CH2:79][OH:80])[C@H:76]([OH:81])[C@H:75]([OH:82])[C@H:74]5[OH:83])[C@H:36]([OH:37])[C@H:35]4[NH:44][C:45](=[O:47])[CH3:46])[O:30][C@@H:19]([O:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26]([O:28][CH3:29])=[O:27])[C@H:18]([OH:48])[C@H:17]3[OH:49])[C@H:5]([NH:4][C:1](=[O:3])[CH3:2])[C@H:10]2[OH:11])[O:30][C@H:31]([CH2:32][OH:33])[C@H:16]([OH:15])[C@H:17]([OH:49])[C@H:18]1[OH:48]

Participants

5

Reactant 2

HCID 15932587HCID 15932587, compoundHCID 54584734HCID 54584734, compound

Product 1

HCID 54227580HCID 54227580, compound

Reagents, catalysts & solvents 2

HCID 10313134Manganese(2+) dichlorideCatalystHCID 2724247Sodium CacodylateSolvent

Procedure

A solution of compound 20 of Example 20 (72 mg), UDP-galactose, (190 mg), bovine galactosyltransferase (6.25 U) and bovine serum albumin (3 mg) in 30 mM sodium cacodylate buffer (7 mL, pH 7.0) containing manganese chloride (40 umol) was incubated at 37° C. for 22 h. The reaction mixture was diluted to 20 mL and purified as described in Example 21. Yield of the product was 98 mg. The structural identity of titled compound 26 was unambiguously assigned by 1H-- and 13C-n.m.r (see Tables 4 and 5, respectively).

Workup

  1. additionThe reaction mixture was diluted to 20 mL
  2. custompurified

Sources & evidence

ORD record
ord-58e7e751f49346a7a40069fc1370da35
Source dataset
uspto-grants-1993_10
Patent number
US05254676

Reaction notes

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