Bromotrimethylsilane → (((2S,3S,4R,5R,6S)-3,4,5-tris(benzyloxy)-6-methyltetrahydro-2H-pyran-2-yl)methyl)phosphonic acid

HRID 522168Notes

Reaction equation

HRID 522168 reaction equation
Br[Si](C)(C)C.[CH2:6]([O:13][C@H:14]1[C@H:19]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C@H:18]([O:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C@H:17]([CH3:36])[O:16][C@@H:15]1[CH2:37][P:38](=[O:45])([O:42]CC)[O:39]CC)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>C(Cl)Cl>[CH2:6]([O:13][C@H:14]1[C@H:19]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C@H:18]([O:28][CH2:29][C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[C@H:17]([CH3:36])[O:16][C@@H:15]1[CH2:37][P:38](=[O:39])([OH:42])[OH:45])[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 76113BromotrimethylsilaneHCID 11238435diethyl (((2S,3S,4R,5R,6S)-3,4,5-tris(benzyloxy)-6-methyltetrahydro-2H-pyran-2-yl)methyl)phosphonate

Product 1

HCID 90357876(((2S,3S,4R,5R,6S)-3,4,5-tris(benzyloxy)-6-methyltetrahydro-2H-pyran-2-yl)methyl)phosphonic acidYield 104.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Bromotrimethylsilane (0.255 mL, 1.93 mmol, commercially available from Sigma Aldrich) was added dropwise to a stirred solution of diethyl (((2S,3S,4R,5R,6S)-3,4,5-tris(benzyloxy)-6-methyltetrahydro-2H-pyran-2-yl)methyl)phosphonate (0.110 g, 0.193 mmol) in DCM (6 mL) at 0° C. The cooling bath was removed, and the reaction mixture was allowed to warm to room temperature and stir for 21 h. The reaction mixture was concentrated in vacuo. The resulting residue was dissolved in MeOH and stirred for 2 h. The solution was then concentrated in vacuo to give (((2S,3S,4R,5R,6S)-3,4,5-tris(benzyloxy)-6-methyltetrahydro-2H-pyran-2-yl)methyl)phosphonic acid as a light orange oil (0.103 g, 104% yield). The material thus obtained was taken on without further purification.

Workup

  1. customThe cooling bath was removed
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. dissolutionThe resulting residue was dissolved in MeOH
  4. stirringstirred for 2 h
  5. concentrationThe solution was then concentrated in vacuo

Sources & evidence

ORD record
ord-edf49f11ed994cdd91691422be7d4862
Source dataset
uspto-grants-2016_05
Patent number
US09328134B2

Reaction notes

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