HCID 18654244, compound → HCID 18655961, compound
Reaction equation
[C:1]([C:4]([C@@:6]([C:25](=[O:27])C)([C@:8]([C:22](=[O:24])[CH3:23])([C@@:10]([C:19](=[O:21])[CH3:20])([C@@H:12]([CH:14]([C:16](=[O:18])[CH3:17])[OH:15])[OH:13])[OH:11])[OH:9])[OH:7])=[O:5])(=O)C.[C:28]([C:31]([C@@:33]([C:47](=[O:49])C)([C@:35]([C:44](=[O:46])[CH3:45])([C@@:37]([C:41](=[O:43])[CH3:42])([CH2:39][OH:40])[OH:38])[OH:36])[OH:34])=[O:32])(=O)C>>[C:4]([C@:6]([C@:8]([C:22](=[O:24])[CH3:23])([C@@:10]([C:19](=[O:21])[CH3:20])([C@@H:12]([CH:14]([C:16](=[O:18])[CH3:17])[OH:15])[OH:13])[OH:11])[OH:9])([OH:7])[CH:25]=[O:27])(=[O:5])[CH3:1].[C:31]([C@:33]([C@:35]([C:44](=[O:46])[CH3:45])([C@@:37]([C:41](=[O:43])[CH3:42])([CH2:39][OH:40])[OH:38])[OH:36])([OH:34])[CH:47]=[O:49])(=[O:32])[CH3:28]Participants
Procedure
The precursors of the invention can be prepared by selectively hydrolysing the most reactive acyl-group of 1,2,3,4,6-pentaacetyl glucose (PAG), or 1,2,3,4-tetraacetylxylose (TAX), or 1,2,3,6-2',3',4',6'-octaacetyllactose (OAL) to produce 2,3,4,6-tetraacetylglucose, or 2,3,4-triacetylxylose, or 2,3,6-2',3',4',6'-heptaacetyllactose respectively, which may then be reacted with an acid chloride or anhydride of choice. In the same way other sugar deratives, such as 1,2,3,4,6-pentaacetylgalactose, 1,2,3,4-tetraacetyllyxose, 1,2,3,4-tetraacetylarabinose, and 1,2,3,6-2',3',4',6'-octa acetylmaltose, after hydrolysis of the most reactive anomeric acetyl group, will produce 2,3,4,6-tetraacetylglactose, 2,3,4-triacetyllyxose, 2,3,4-triacetylarabinose, and 2,3,6-2',3',4',6'-hepta acetylmaltose respectively, which can then be reacted with an acid chloride or anhydride of choice. Other examples of suitable precursors are those derived from acetylated cellibiose, mannose, fructose, melibiose and ribose.
Workup
- customThe precursors of the invention can be prepared
Sources & evidence
- ORD record
- ord-a207474a016b4790869e23c3b53a3ba0
- Source dataset
- uspto-grants-1994_11
- Patent number
- US05360573
Reaction notes
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