HCID 86752813, compound → HCID 86752812, compound

HRID 964415Notes

Reaction equation

HRID 964415 reaction equation
[CH2:1]([C@@:8]1([O:22][C@H:21]([CH2:23][NH:24][C:25]([C@H:27]([C@H:32]([C@@H:37]([C@H:42]([CH2:47][O:48][C:49](=[O:51])[CH3:50])[O:43][C:44](=[O:46])[CH3:45])[O:38][C:39](=[O:41])[CH3:40])[O:33][C:34](=[O:36])[CH3:35])[O:28][C:29](=[O:31])[CH3:30])=[O:26])[C@@H:16]([O:17][C:18](=[O:20])[CH3:19])[C@H:11]([O:12][C:13](=[O:15])[CH3:14])[C@H:10]1[NH:52]C(OCC1C=CC=CC=1)=O)[OH:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>O1CCOCC1>[CH2:1]([C@@:8]1([O:22][C@H:21]([CH2:23][NH:24][C:25]([C@H:27]([C@H:32]([C@@H:37]([C@H:42]([CH2:47][O:48][C:49](=[O:51])[CH3:50])[O:43][C:44](=[O:46])[CH3:45])[O:38][C:39](=[O:41])[CH3:40])[O:33][C:34](=[O:36])[CH3:35])[O:28][C:29](=[O:31])[CH3:30])=[O:26])[C@@H:16]([O:17][C:18](=[O:20])[CH3:19])[C@H:11]([O:12][C:13](=[O:15])[CH3:14])[C@H:10]1[NH2:52])[OH:9])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 86752813HCID 86752813, compound

Product 1

HCID 86752812HCID 86752812, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

2,3,4,5,6-Penta-O-acetyl-L-gulonic acid (benzyl 3,4-di-O-acetyl-2-benzyloxycarbonylamino-2,6-didesoxy-α-D-glucopyranosid-6-yl)-amide was hydrogenated as described under Ex. 13.B. and gave 2,3,4,5,6-penta-O-acetyl-L-gulonic acid (benzyl 3,4-di-O-acetyl-2-amino-2,6-didesoxy-α-D-glucopyranosid-6-yl)-amide, [α]+75.50 (c 0.2; dioxan), MS: m/z 763.6 ([M+Na]+).

Sources & evidence

ORD record
ord-7e81bbef35de4f02ab783033a284034d
Source dataset
uspto-grants-1998_06
Patent number
US05767268

Reaction notes

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