Tributylstannane → HCID 67287099, compound

HRID 46207Notes

Reaction equation

HRID 46207 reaction equation
Cl[CH:2]([C:12]1[CH:17]=[C:16]([CH:18]2[C@H:23]([O:24][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C@@H:22]([O:32][CH2:33][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[C@H:21]([O:40][CH2:41][C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)[C@@H:20]([CH2:48][O:49][CH2:50][C:51]3[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=3)[O:19]2)[CH:15]=[CH:14][C:13]=1[Cl:57])[C:3]1[N:4]=[N:5][C:6]([O:9][CH2:10][CH3:11])=[CH:7][CH:8]=1.CC(N=NC(C#N)(C)C)(C#N)C.C([SnH](CCCC)CCCC)CCC>C1(C)C=CC=CC=1>[Cl:57][C:13]1[CH:14]=[CH:15][C:16]([CH:18]2[C@H:23]([O:24][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C@@H:22]([O:32][CH2:33][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[C@H:21]([O:40][CH2:41][C:42]3[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=3)[C@@H:20]([CH2:48][O:49][CH2:50][C:51]3[CH:52]=[CH:53][CH:54]=[CH:55][CH:56]=3)[O:19]2)=[CH:17][C:12]=1[CH2:2][C:3]1[N:4]=[N:5][C:6]([O:9][CH2:10][CH3:11])=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 5948TributylstannaneHCID 6547AzobisisobutyronitrileHCID 672873733-(chloro(2-chloro-5-((3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran-2-yl)phenyl)methyl)-6-ethoxypyridazine

Product 1

HCID 67287099HCID 67287099, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 3-(chloro(2-chloro-5-((3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran-2-yl)phenyl)methyl)-6-ethoxypyridazine (589 mg; 0.73 mmol) in anhydrous toluene (10 mL) was added catalytic amounts of AIBN and tributyltin hydride (0.3 mL; 1.10 mmol) at room temperature under nitrogen gas. The reaction solution was then heated at 80° C. until reaction was completed. The solution was coded to room temperature and toluene was removed on evaporator. The crude α/β mixture was purified by silica gel column chromatography with KF pad (eluent: hexane/EtOAc mixture (60/40; v/v)). The purified α/β mixture was separated by using Gilson prep HPLC system and then obtained α configured product (123 mg; 0.16 mmol) and β configured product (105 mg; 0.14 mmol) as colorless oil.

Workup

  1. customwas coded to room temperature
  2. customtoluene was removed on evaporator
  3. customThe crude α/β mixture was purified by silica gel column chromatography with KF pad (eluent: hexane/EtOAc mixture (60/40; v/v))
  4. customThe purified α/β mixture was separated
  5. customobtained α configured product (123 mg; 0.16 mmol) and β configured product (105 mg; 0.14 mmol) as colorless oil

Sources & evidence

ORD record
ord-a32e256a7b31467d902567c891ec98ff
Source dataset
uspto-grants-2013_09
Patent number
US08541380B2

Reaction notes

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