Tributylstannane → HCID 86714095, compound

HRID 2206806Notes

Reaction equation

HRID 2206806 reaction equation
[CH2:1]([O:4][C:5]1[C:10](Br)=[C:9]([Cl:12])[C:8]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH3:22])=[CH:16][CH:15]=2)=[CH:7][C:6]=1[CH:23]1[C@H:28]([O:29][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C@@H:27]([O:37][CH2:38][C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[C@H:26]([O:45][CH2:46][C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)[C@@H:25]([CH2:53][O:54][CH2:55][C:56]2[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=2)[O:24]1)[CH:2]=[CH2:3].C([SnH](CCCC)CCCC)CCC.CC(N=NC(C#N)(C)C)(C#N)C>C1(C)C=CC=CC=1>[Cl:12][C:9]1[C:10]2[CH:2]([CH3:3])[CH2:1][O:4][C:5]=2[C:6]([CH:23]2[C@H:28]([O:29][CH2:30][C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=3)[C@@H:27]([O:37][CH2:38][C:39]3[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=3)[C@H:26]([O:45][CH2:46][C:47]3[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=3)[C@@H:25]([CH2:53][O:54][CH2:55][C:56]3[CH:57]=[CH:58][CH:59]=[CH:60][CH:61]=3)[O:24]2)=[CH:7][C:8]=1[CH2:13][C:14]1[CH:15]=[CH:16][C:17]([O:20][CH2:21][CH3:22])=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 5948TributylstannaneHCID 6547AzobisisobutyronitrileHCID 86714093HCID 86714093, compound

Product 1

HCID 86714095HCID 86714095, compoundYield 34.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of (3S,4R,5R,6R)-2-(2-(allyloxy)-3-bromo-4-chloro-5-(4-ethoxybenzyl)phenyl)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran (325 mg, 0.359 mmole) in toluene (15 mL) were added tributyltin hydride (0.29 mL, 1.08 mmole) and AIBN (5.9 mg, 0.0359 mmole) in one portion. The resulting solution was refluxed overnight. The reaction mixture was filtered on the KF pad followed by concentrated in vacuo. The crude residue was purified on Biotage® purification apparatus to yield the title compound (102 mg, 34%) as a colorless gum.

Workup

  1. temperatureThe resulting solution was refluxed overnight
  2. filtrationThe reaction mixture was filtered on the KF pad
  3. concentrationby concentrated in vacuo
  4. customThe crude residue was purified on Biotage® purification apparatus

Sources & evidence

ORD record
ord-fb9dcc0402394dddbffa094bcb71e575
Source dataset
uspto-grants-2016_06
Patent number
US09371303B2

Reaction notes

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