Imidazole → (5S,7S)-2-[5,7-bis-(tert-butyl-diphenyl-silanyloxy)-non-8-en-2-ynyloxy]-tetrahydropyran

HRID 581620Notes

Reaction equation

HRID 581620 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][C:9]#[C:10][CH2:11][C@H:12]([OH:18])[CH2:13][C@H:14]([OH:17])[CH:15]=[CH2:16].CN(C=O)C.N1[CH:28]=[CH:27]N=C1.[C:29]([Si:33](Cl)([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)([CH3:32])([CH3:31])[CH3:30]>CCCCCC.CCOC(C)=O>[C:29]([Si:33]([C:28]1[CH:27]=[CH:45][CH:40]=[CH:41][CH:42]=1)([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[O:18][C@H:12]([CH2:13][C@H:14]([O:17][Si:33]([C:29]([CH3:32])([CH3:31])[CH3:30])([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[CH:15]=[CH2:16])[CH2:11][C:10]#[C:9][CH2:8][O:7][CH:2]1[CH2:3][CH2:4][CH2:5][CH2:6][O:1]1)([CH3:32])([CH3:31])[CH3:30]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 6228DimethylformamideHCID 94078tert-ButyldiphenylchlorosilaneHCID 57143448(3S,5S)-9-(tetrahydro-pyran-2-yloxy)-non-1-en-7-yne-3,5-diol

Product 1

HCID 57039693(5S,7S)-2-[5,7-bis-(tert-butyl-diphenyl-silanyloxy)-non-8-en-2-ynyloxy]-tetrahydropyran

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

10.40 g (40.9 mmol) of (3S,5S)-9-(tetrahydro-pyran-2-yloxy)-non-1-en-7-yne-3,5-diol was dissolved in 30 ml of abs. DMF and treated successively with 18.9 g (6.8 eq.) of imidazole and 35.5 ml (3.4 eq.) of tert-butyl-chloro-diphenylsilane. After stirring for 20 h at 40°, the reaction mixture was poured onto crushed ice/EtOEt. Usual workup followed by flash chromatography (SiO2, hexane/AcOEt=96/6) gave 25.16 g of (5S,7S)-2-[5,7-bis-(tert-butyl-diphenyl-silanyloxy)-non-8-en-2-ynyloxy]-tetrahydropyran as colorless oil (1:1 epimeric mixture).

Workup

  1. additionthe reaction mixture was poured

Sources & evidence

ORD record
ord-a5d60e0b8e3d41d6bf7228f017425053
Source dataset
uspto-grants-1999_07
Patent number
US05919986

Reaction notes

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