5-bromo-3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-beta-D-xylo-pyranoside → HCID 67291306, compound

HRID 1685429Notes

Reaction equation

HRID 1685429 reaction equation
[C:1]([O:4][C@@H:5]1[C@@H:18]([O:19][C:20](=[O:22])[CH3:21])[C@H:17]([O:23][C:24](=[O:26])[CH3:25])[CH2:16][S:15][C@H:6]1[O:7][C:8]1[CH:9]=[N:10][CH:11]=[C:12](Br)[CH:13]=1)(=[O:3])[CH3:2].C[C:28]1[CH:33]=[CH:32][C:31](B(O)OOCC)=[CH:30][CH:29]=1>>[C:1]([O:4][C@@H:5]1[C@@H:18]([O:19][C:20](=[O:22])[CH3:21])[C@H:17]([O:23][C:24](=[O:26])[CH3:25])[CH2:16][S:15][C@H:6]1[O:7][C:8]1[CH:9]=[N:10][CH:11]=[C:12]([C:28]2[CH:29]=[CH:30][C:31]([O:4][CH:5]([CH3:18])[CH3:6])=[CH:32][CH:33]=2)[CH:13]=1)(=[O:3])[CH3:2]

Participants

3

Reactant 2

HCID 441955025-bromo-3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-beta-D-xylo-pyranosideHCID 86625026HCID 86625026, compound

Product 1

HCID 67291306HCID 67291306, compound

Procedure

By following a procedure analogous to Example 27 starting from 5-bromo-3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside and 4-methylethoxy-phenylboronic acid, 5-[4-(1-methylethoxy)phenyl]-3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside is obtained in the form of a white solid (yield=55%).

Sources & evidence

ORD record
ord-02c764f9af8d4e4ea60b3f9931bc460e
Source dataset
uspto-grants-2012_04
Patent number
US08148407B2

Reaction notes

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