alpha-D-Glucopyranosyl bromide, tetraacetate → HCID 68945246, compound

HRID 1869014Notes

Reaction equation

[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][C:20]2[C:21](=[O:28])[NH:22][NH:23][C:24]=2[CH:25]([CH3:27])[CH3:26])=[C:15]([CH3:29])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:30][C:31]([O:33][CH2:34][C@H:35]1[O:40][C@H:39](Br)[C@H:38]([O:42][C:43]([CH3:45])=[O:44])[C@@H:37]([O:46][C:47]([CH3:49])=[O:48])[C@H:36]1[O:50][C:51]([CH3:53])=[O:52])=[O:32].CC(OC[C@H]1O[C@H](Br)[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H]1OC(C)=O)=O>>[C:43]([O:42][C@@H:38]1[C@@H:37]([O:46][C:47](=[O:48])[CH3:49])[C@@H:36]([O:50][C:51](=[O:52])[CH3:53])[C@@H:35]([CH2:34][O:33][C:31](=[O:32])[CH3:30])[O:40][C@H:39]1[O:28][C:21]1[C:20]([CH2:19][C:16]2[CH:17]=[CH:18][C:13]([O:12][CH2:11][CH2:10][CH2:9][O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[CH:14][C:15]=2[CH3:29])=[C:24]([CH:25]([CH3:27])[CH3:26])[NH:23][N:22]=1)(=[O:44])[CH3:45]

Participants

Reactant 3

HCID 101776alpha-D-Glucopyranosyl bromide, tetraacetate

HCID 2734143alpha-Acetobromogalactose

HCID 68945240HCID 68945240, compound

Product 1

HCID 68945246HCID 68945246, compound

Procedure

The title compound was prepared in a similar manner to that described in Reference Example 17 using 4-{[4-(3-benzyloxypropoxy)-2-methylphenyl]methyl}-1,2-dihydro-5-isopropyl-3H-pyrazol-3-one and acetobromo-α-D-galactose instead of 4-{[4-(3-benzyloxypropoxy)phenyl]methyl}-1,2-dihydro-5-isopropyl-3H-pyrazol-3-one and acetobromo-α-D-glucose, respectively.

Sources & evidence

ORD record: ord-363e0de71d054734a28bbb46bc6429d9
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07635684B2

Reaction notes

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