(2R,9S,10S)-2-(Benzyloxy)-9,10-epoxy-11-(tert-butyldimethylsiloxy)-4-undecyne

Base Information

Chemical Name:(2R,9S,10S)-2-(Benzyloxy)-9,10-epoxy-11-(tert-butyldimethylsiloxy)-4-undecyne
CAS No.:152896-89-4
Molecular Formula:C₂₄H₃₈O₃Si
Molecular Weight:402.649
Hs Code.:

Synonyms:(2R,9S,10S)-2-(Benzyloxy)-9,10-epoxy-11-(tert-butyldimethylsiloxy)-4-undecyne

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (2R,9S,10S)-2-(Benzyloxy)-9,10-epoxy-11-(tert-butyldimethylsiloxy)-4-undecyne

Chemical Property:

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Technology Process of (2R,9S,10S)-2-(Benzyloxy)-9,10-epoxy-11-(tert-butyldimethylsiloxy)-4-undecyne

There total 11 articles about (2R,9S,10S)-2-(Benzyloxy)-9,10-epoxy-11-(tert-butyldimethylsiloxy)-4-undecyne which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

: 124887-05-4
(2S,3S,10R)-10-(Benzyloxy)-2,3-epoxy-7-undecyn-1-ol

: 18162-48-6
tert-butyldimethylsilyl chloride

: 152896-89-4
(2R,9S,10S)-2-(Benzyloxy)-9,10-epoxy-11-(tert-butyldimethylsiloxy)-4-undecyne

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; for 2h;
DOI:10.1021/jo00077a047

Reference yield:

: 124887-04-3
(2E,10R)-10-(Benzyloxy)undec-2-en-7-yn-1-ol

: 152896-89-4
(2R,9S,10S)-2-(Benzyloxy)-9,10-epoxy-11-(tert-butyldimethylsiloxy)-4-undecyne

Guidance literature:: Multi-step reaction with 2 steps

1: 92 percent / 1.) diethyl (+)-L-tertrate, Ti(O-i-Pr)4, molecular sieves 4 Angstroem, t-BuOOH / CH₂Cl₂ / 1.) -20 deg C to -15 deg C, 0.5 h, 2.) -20 deg C to -15 deg C, 3.5 h

2: 99 percent / imidazole / dimethylformamide / 2 h

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; 4 A molecular sieve; (+)-Weinsaeure-diethylester; In dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo00077a047

Reference yield:

: 1720-37-2
2-(hex-5-yn-1-yloxy)tetrahydro-2H-pyran

: 152896-89-4
(2R,9S,10S)-2-(Benzyloxy)-9,10-epoxy-11-(tert-butyldimethylsiloxy)-4-undecyne

Guidance literature:: Multi-step reaction with 8 steps

1: 65 percent / n-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide; hexane / 1.) 0 deg C, 45 min, 2.) room temp., overnight

2: 68 percent / NaH, n-Bu₄NI / tetrahydrofuran

3: p-TsOH / methanol / 2 h

4: 1.) (COCl)2, DMSO, 2.) Et₃N / CH₂Cl₂ / 1.) -78 deg C, 20 min, 2.) -78 deg C to room temp.

5: 75 percent / LiCl, i-Pr₂NEt / acetonitrile / 1.) 15 min, room temp., 2.) room temp., overnight

6: 80 percent / DIBALH / diethyl ether / 2.5 h / 0 °C

7: 92 percent / 1.) diethyl (+)-L-tertrate, Ti(O-i-Pr)4, molecular sieves 4 Angstroem, t-BuOOH / CH₂Cl₂ / 1.) -20 deg C to -15 deg C, 0.5 h, 2.) -20 deg C to -15 deg C, 3.5 h

8: 99 percent / imidazole / dimethylformamide / 2 h

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; n-butyllithium; oxalyl dichloride; 4 A molecular sieve; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; (+)-Weinsaeure-diethylester; triethylamine; N-ethyl-N,N-diisopropylamine; lithium chloride; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/jo00077a047