2,3-di(benzyloxy)-4-tert-butyldimethylsilyloxy-(2S,3R,4S)-octane

Base Information

Chemical Name:2,3-di(benzyloxy)-4-tert-butyldimethylsilyloxy-(2S,3R,4S)-octane
CAS No.:790664-69-6
Molecular Formula:C₂₉H₄₆O₃Si
Molecular Weight:470.768
Hs Code.:

Synonyms:2,3-di(benzyloxy)-4-tert-butyldimethylsilyloxy-(2S,3R,4S)-octane

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Chemical Property of 2,3-di(benzyloxy)-4-tert-butyldimethylsilyloxy-(2S,3R,4S)-octane

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Technology Process of 2,3-di(benzyloxy)-4-tert-butyldimethylsilyloxy-(2S,3R,4S)-octane

There total 5 articles about 2,3-di(benzyloxy)-4-tert-butyldimethylsilyloxy-(2S,3R,4S)-octane 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: 88.0%

: 100-39-0
benzyl bromide

: 790664-68-5
1-[1-benzyloxy-(1S)-ethyl]-2-tert-butyldimethylsilyloxymethyl-(1R,2S)-hexyl alcohol

: 790664-69-6
2,3-di(benzyloxy)-4-tert-butyldimethylsilyloxy-(2S,3R,4S)-octane

Guidance literature:: 1-[1-benzyloxy-(1S)-ethyl]-2-tert-butyldimethylsilyloxymethyl-(1R,2S)-hexyl alcohol; With sodium hydride; In N,N-dimethyl-formamide; at 0 ℃; for 0.25h;

benzyl bromide; In N,N-dimethyl-formamide; at 20 ℃; for 0.5h;
DOI:10.1055/s-2004-829173

Reference yield:

: 119242-60-3
4-benzyloxy-(Z,4S)-2-penten-1-ol

: 790664-69-6
2,3-di(benzyloxy)-4-tert-butyldimethylsilyloxy-(2S,3R,4S)-octane

Guidance literature:: Multi-step reaction with 4 steps

1.1: 55.5 percent / (-)-diethyl tartrate; titanium isopropoxide; cumene hydroperoxide / 4 Angstroem molecular sieves / CH₂Cl₂ / 360 h / -20 °C

2.1: copper(I) iodide / diethyl ether; hexane / 0.5 h / -20 °C

2.2: 75.5 percent / diethyl ether; hexane / 1 h / -20 °C

3.1: 81 percent / imidazole / CH₂Cl₂ / 1 h / 20 °C

4.1: NaH / dimethylformamide / 0.25 h / 0 °C

4.2: 88 percent / dimethylformamide / 0.5 h / 20 °C

With 1H-imidazole; titanium(IV) isopropylate; copper(l) iodide; Cumene hydroperoxide; sodium hydride; (-)-diethyl tartrate; 4 A molecular sieve; In diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; 1.1: Sharpless asymmetric epoxidation;
DOI:10.1055/s-2004-829173

Reference yield:

: ethyl 4-benzyloxy-(E/Z,4S)-2-pentenoate

: 790664-69-6
2,3-di(benzyloxy)-4-tert-butyldimethylsilyloxy-(2S,3R,4S)-octane

Guidance literature:: Multi-step reaction with 5 steps

1.1: 81 percent / DIBAL-H / toluene; CH₂Cl₂ / 0.5 h / -20 °C

2.1: 55.5 percent / (-)-diethyl tartrate; titanium isopropoxide; cumene hydroperoxide / 4 Angstroem molecular sieves / CH₂Cl₂ / 360 h / -20 °C

3.1: copper(I) iodide / diethyl ether; hexane / 0.5 h / -20 °C

3.2: 75.5 percent / diethyl ether; hexane / 1 h / -20 °C

4.1: 81 percent / imidazole / CH₂Cl₂ / 1 h / 20 °C

5.1: NaH / dimethylformamide / 0.25 h / 0 °C

5.2: 88 percent / dimethylformamide / 0.5 h / 20 °C

With 1H-imidazole; titanium(IV) isopropylate; copper(l) iodide; Cumene hydroperoxide; sodium hydride; diisobutylaluminium hydride; (-)-diethyl tartrate; 4 A molecular sieve; In diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; 2.1: Sharpless asymmetric epoxidation;
DOI:10.1055/s-2004-829173