(2S,4S,5S)-6-(benzyloxy)-5-(tert-butoxycarbonylamino)-4-(tert-butyldimethylsilyloxy)-2-isopropylhexanoic acid

Base Information

Chemical Name:(2S,4S,5S)-6-(benzyloxy)-5-(tert-butoxycarbonylamino)-4-(tert-butyldimethylsilyloxy)-2-isopropylhexanoic acid
CAS No.:1056676-10-8
Molecular Formula:C₂₇H₄₇NO₆Si
Molecular Weight:509.759
Hs Code.:

Synonyms:(2S,4S,5S)-6-(benzyloxy)-5-(tert-butoxycarbonylamino)-4-(tert-butyldimethylsilyloxy)-2-isopropylhexanoic acid

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Chemical Property of (2S,4S,5S)-6-(benzyloxy)-5-(tert-butoxycarbonylamino)-4-(tert-butyldimethylsilyloxy)-2-isopropylhexanoic acid

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Technology Process of (2S,4S,5S)-6-(benzyloxy)-5-(tert-butoxycarbonylamino)-4-(tert-butyldimethylsilyloxy)-2-isopropylhexanoic acid

There total 10 articles about (2S,4S,5S)-6-(benzyloxy)-5-(tert-butoxycarbonylamino)-4-(tert-butyldimethylsilyloxy)-2-isopropylhexanoic acid 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: 50.0%

: 1056676-05-1
[(S)-2-benzyloxy-1-((2S,4S)-4-isopropyl-5-oxo-tetrahydro-furan-2-yl)-ethyl]-carbamic acid tert-butyl ester

: 18162-48-6
tert-butyldimethylsilyl chloride

: 1056676-10-8
(2S,4S,5S)-6-(benzyloxy)-5-(tert-butoxycarbonylamino)-4-(tert-butyldimethylsilyloxy)-2-isopropylhexanoic acid

Guidance literature:: [(S)-2-benzyloxy-1-((2S,4S)-4-isopropyl-5-oxo-tetrahydro-furan-2-yl)-ethyl]-carbamic acid tert-butyl ester; With lithium hydroxide; water; In 1,4-dioxane; at 20 ℃; for 1h;

With citric acid; In diethyl ether; water;

tert-butyldimethylsilyl chloride; With 1H-imidazole; methanol; more than 3 stages;

Reference yield:

: 1148105-68-3
C₂₁H₃₃NO₆

: 18162-48-6
tert-butyldimethylsilyl chloride

: 1056676-10-8
(2S,4S,5S)-6-(benzyloxy)-5-(tert-butoxycarbonylamino)-4-(tert-butyldimethylsilyloxy)-2-isopropylhexanoic acid

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃; for 48h;

Reference yield:

: 906662-73-5
(4S,1'S)-4-(1-hydroxy-3-methoxycarbonylprop-2-ynyl)-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester

: 1056676-10-8
(2S,4S,5S)-6-(benzyloxy)-5-(tert-butoxycarbonylamino)-4-(tert-butyldimethylsilyloxy)-2-isopropylhexanoic acid

Guidance literature:: Multi-step reaction with 8 steps

1: hydrogen / palladium on activated charcoal / ethyl acetate / 3 h

2: acetic acid / toluene / 4 - 5 h / Heating / reflux

3: n-butyllithium; diisopropylamine / tetrahydrofuran; hexanes; tripyrrolidine phosphorus oxide / 4.5 h / -78 - 20 °C

4: water; trifluoroacetic acid / 1 h / 20 °C

5: sodium carbonate / 1,4-dioxane; water / 2 h / 20 °C

6: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 20 °C

7: lithium hydroxide; water / 1,4-dioxane / 1 h / 20 °C

8: 1H-imidazole / N,N-dimethyl-formamide / 48 h / 20 °C

With 1H-imidazole; lithium hydroxide; n-butyllithium; trimethylsilyl trifluoromethanesulfonate; water; hydrogen; sodium carbonate; acetic acid; diisopropylamine; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; hexanes; dichloromethane; tripyrrolidine phosphorus oxide; water; ethyl acetate; N,N-dimethyl-formamide; toluene;