(4-(Piperidin-1-yl)phenyl)boronic acid → 6-[4-(1-piperidinyl)phenyl]-3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-beta-D-xylo-pyranoside

HRID 1685454Notes

Reaction equation

HRID 1685454 reaction equation
[N:1]1([C:7]2[CH:12]=[CH:11][C:10](B(O)O)=[CH:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:16]([O:19][C@@H:20]1[C@@H:33]([O:34][C:35](=[O:37])[CH3:36])[C@H:32]([O:38][C:39](=[O:41])[CH3:40])[CH2:31][S:30][C@H:21]1[O:22][C:23]1[CH:24]=[N:25][C:26](Br)=[CH:27][CH:28]=1)(=[O:18])[CH3:17]>>[C:16]([O:19][C@@H:20]1[C@@H:33]([O:34][C:35](=[O:37])[CH3:36])[C@H:32]([O:38][C:39](=[O:41])[CH3:40])[CH2:31][S:30][C@H:21]1[O:22][C:23]1[CH:24]=[N:25][C:26]([C:10]2[CH:11]=[CH:12][C:7]([N:1]3[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]3)=[CH:8][CH:9]=2)=[CH:27][CH:28]=1)(=[O:18])[CH3:17]

Participants

3

Reactant 2

HCID 4192665(4-(Piperidin-1-yl)phenyl)boronic acidHCID 86625029HCID 86625029, compound

Product 1

HCID 672925406-[4-(1-piperidinyl)phenyl]-3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-beta-D-xylo-pyranoside

Procedure

By following a procedure analogous to Example 43 starting from [4-(1-piperidinyl)phenyl]boronic acid and 6-bromo-3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside, the expected compound is obtained in the form of a gray powder (yield=14%).

Sources & evidence

ORD record
ord-c347c10a6d50447a9b70ce8c6fc1fb0a
Source dataset
uspto-grants-2012_04
Patent number
US08148407B2

Reaction notes

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