(2R,3S)-1-[(tert-butyldimethylsilyl)oxy]-3-[(tert-butoxycarbonyl)amino]-4-cyclohexyl-2-[(p-nitrobenzoyl)oxy]butane

Base Information

Chemical Name:(2R,3S)-1-[(tert-butyldimethylsilyl)oxy]-3-[(tert-butoxycarbonyl)amino]-4-cyclohexyl-2-[(p-nitrobenzoyl)oxy]butane
CAS No.:180891-91-2
Molecular Formula:C₂₈H₄₆N₂O₇Si
Molecular Weight:550.768
Hs Code.:

Synonyms:(2R,3S)-1-[(tert-butyldimethylsilyl)oxy]-3-[(tert-butoxycarbonyl)amino]-4-cyclohexyl-2-[(p-nitrobenzoyl)oxy]butane

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Chemical Property of (2R,3S)-1-[(tert-butyldimethylsilyl)oxy]-3-[(tert-butoxycarbonyl)amino]-4-cyclohexyl-2-[(p-nitrobenzoyl)oxy]butane

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Technology Process of (2R,3S)-1-[(tert-butyldimethylsilyl)oxy]-3-[(tert-butoxycarbonyl)amino]-4-cyclohexyl-2-[(p-nitrobenzoyl)oxy]butane

There total 9 articles about (2R,3S)-1-[(tert-butyldimethylsilyl)oxy]-3-[(tert-butoxycarbonyl)amino]-4-cyclohexyl-2-[(p-nitrobenzoyl)oxy]butane 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: 89.0%

: 165683-84-1
(2S,3S)-1-[(tert-butyldimethylsilyl)oxy]-3-[(tert-butoxycarbonyl)amino]-4-cyclohexyl-2-butanol

: 62-23-7
4-nitro-benzoic acid

: 180891-91-2
(2R,3S)-1-[(tert-butyldimethylsilyl)oxy]-3-[(tert-butoxycarbonyl)amino]-4-cyclohexyl-2-[(p-nitrobenzoyl)oxy]butane

Guidance literature:: With triphenylphosphine; diethylazodicarboxylate; In benzene; at 20 ℃; for 12h;
DOI:10.1021/jo960351p

Reference yield:

: 24424-99-5
di-tert-butyl dicarbonate

: 180891-91-2
(2R,3S)-1-[(tert-butyldimethylsilyl)oxy]-3-[(tert-butoxycarbonyl)amino]-4-cyclohexyl-2-[(p-nitrobenzoyl)oxy]butane

Guidance literature:: Multi-step reaction with 3 steps

1: 85 percent / H₂ / Pd(OH)2/C / ethyl acetate / 760 Torr

2: 83 percent / imidazole / dimethylformamide / 48 h / 20 °C

3: 89 percent / PPh₃; diethyl azodicarboxylate / benzene / 12 h / 20 °C

With 1H-imidazole; hydrogen; triphenylphosphine; diethylazodicarboxylate; palladium dihydroxide; In ethyl acetate; N,N-dimethyl-formamide; benzene; 1: Hydrogenolysis / 2: silylation / 3: Mitsunobu reaction;
DOI:10.1021/jo960351p

Reference yield:

: 1589-44-2
(E)-4-cyclohexyl-2-buten-1-ol

: 180891-91-2
(2R,3S)-1-[(tert-butyldimethylsilyl)oxy]-3-[(tert-butoxycarbonyl)amino]-4-cyclohexyl-2-[(p-nitrobenzoyl)oxy]butane

Guidance literature:: Multi-step reaction with 5 steps

1.1: 4 Angstroem molecular sieves; D-(-)-diisopropyl tartrate / titanium tetraisopropoxide / CH₂Cl₂ / 0.5 h / -20 °C

1.2: tert-butyl hydroperoxide / CH₂Cl₂; 2,2,4-trimethyl-pentane / 24 h / -20 °C

2.1: 99 percent / titanium diazidodiisopropoxide / benzene / 0.13 h / 75 °C

3.1: 97 percent / H₂ / Pd/C / ethyl acetate / 18 h / 760 Torr

4.1: 83 percent / imidazole / dimethylformamide / 48 h / 20 °C

5.1: 89 percent / PPh₃; diethyl azodicarboxylate / benzene / 12 h / 20 °C

With 1H-imidazole; diisopropoxytitanium diazide; 4 A molecular sieve; hydrogen; D-(-)-diisopropyl tartrate; triphenylphosphine; diethylazodicarboxylate; titanium(IV) isopropylate; palladium on activated charcoal; In dichloromethane; ethyl acetate; N,N-dimethyl-formamide; benzene; 1.1: Sharpless epoxidation / 1.2: Sharpless epoxidation / 2.1: Ring cleavage / 3.1: Hydrogenolysis / 4.1: silylation / 5.1: Mitsunobu reaction;
DOI:10.1021/jo960351p