D-Ribonic acid (benzyl 2-benzyloxycarbonylamino-2,6-didesoxy-alpha-D-glucopyranosid-6-yl)-amide → 2,3,4,5-tetra-O-acetyl-D-ribonic acid (benzyl 3,4-di-O-acetyl-2-benzyloxycarbonylamino-2,6-didesoxy-alpha-D-glucopyranosid-6-yl)-amide

HRID 964409Notes

Reaction equation

HRID 964409 reaction equation
[CH2:1]([C@@:8]1([O:16][C@H:15]([CH2:17][NH:18][C:19]([C@@H:21]([C@@H:23]([C@@H:25]([CH2:27][OH:28])[OH:26])[OH:24])[OH:22])=[O:20])[C@@H:13]([OH:14])[C@H:11]([OH:12])[C@H:10]1[NH:29][C:30]([O:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)=[O:31])[OH:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>O1CCOCC1>[CH2:1]([C@@:8]1([O:16][C@H:15]([CH2:17][NH:18][C:19]([C@@H:21]([C@@H:23]([C@@H:25]([CH2:27][O:28][C:8](=[O:9])[CH3:1])[O:26][C:11](=[O:12])[CH3:10])[O:24][C:19](=[O:20])[CH3:21])[O:22][C:23](=[O:24])[CH3:25])=[O:20])[C@@H:13]([O:14][C:33](=[O:32])[CH3:34])[C@H:11]([O:12][C:13](=[O:14])[CH3:15])[C@H:10]1[NH:29][C:30]([O:32][CH2:33][C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1)=[O:31])[OH:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 86752800D-Ribonic acid (benzyl 2-benzyloxycarbonylamino-2,6-didesoxy-alpha-D-glucopyranosid-6-yl)-amide

Product 1

HCID 867528012,3,4,5-tetra-O-acetyl-D-ribonic acid (benzyl 3,4-di-O-acetyl-2-benzyloxycarbonylamino-2,6-didesoxy-alpha-D-glucopyranosid-6-yl)-amide

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

D-Ribonic acid (benzyl 2-benzyloxycarbonylamino-2,6-didesoxy-α-D-glucopyranosid-6-yl)-amide was acetylated as described in Ex. 14.B. and gave 2,3,4,5-tetra-O-acetyl-D-ribonic acid (benzyl 3,4-di-O-acetyl-2-benzyloxycarbonylamino-2,6-didesoxy-α-D-glucopyranosid-6-yl)-amide, [α]+78.0° (c 0.2; dioxan), MS: m/z 803.2 ([M+H]+).

Sources & evidence

ORD record
ord-13d991f88f954d2ca8f219e80f13e95b
Source dataset
uspto-grants-1998_06
Patent number
US05767268

Reaction notes

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