(3S,4R,5S)-4-Benzyloxycarbonylamino-5-methyl-3-triisopropylsilanyloxy-heptanoic acid (S)-1-allyloxycarbonyl-2-methyl-propyl ester

Base Information

Chemical Name:(3S,4R,5S)-4-Benzyloxycarbonylamino-5-methyl-3-triisopropylsilanyloxy-heptanoic acid (S)-1-allyloxycarbonyl-2-methyl-propyl ester
CAS No.:250039-51-1
Molecular Formula:C₃₃H₅₅NO₇Si
Molecular Weight:605.888
Hs Code.:

Synonyms:(3S,4R,5S)-4-Benzyloxycarbonylamino-5-methyl-3-triisopropylsilanyloxy-heptanoic acid (S)-1-allyloxycarbonyl-2-methyl-propyl ester

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Chemical Property of (3S,4R,5S)-4-Benzyloxycarbonylamino-5-methyl-3-triisopropylsilanyloxy-heptanoic acid (S)-1-allyloxycarbonyl-2-methyl-propyl ester

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Technology Process of (3S,4R,5S)-4-Benzyloxycarbonylamino-5-methyl-3-triisopropylsilanyloxy-heptanoic acid (S)-1-allyloxycarbonyl-2-methyl-propyl ester

There total 13 articles about (3S,4R,5S)-4-Benzyloxycarbonylamino-5-methyl-3-triisopropylsilanyloxy-heptanoic acid (S)-1-allyloxycarbonyl-2-methyl-propyl ester 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: 65.0%

: 178113-56-9
L-2-hydroxy-3-methylbutanoic acid allyl ester

: 250039-50-0
(3S,4R,5S)-4-benzyloxycarbonylamino-5-methyl-3-(triisopropylsilanyloxy) heptanoic acid

: 250039-51-1
(3S,4R,5S)-4-Benzyloxycarbonylamino-5-methyl-3-triisopropylsilanyloxy-heptanoic acid (S)-1-allyloxycarbonyl-2-methyl-propyl ester

Guidance literature:: With dmap; dicyclohexyl-carbodiimide; at 0 - 20 ℃;
DOI:10.1021/ja010222c

Reference yield:

: 80522-42-5
triisopropylsilyl trifluoromethanesulfonate

: 250039-51-1
(3S,4R,5S)-4-Benzyloxycarbonylamino-5-methyl-3-triisopropylsilanyloxy-heptanoic acid (S)-1-allyloxycarbonyl-2-methyl-propyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 1.204 g / 2,6-lutidine / CH₂Cl₂ / 2.5 h / 0 - 20 °C

2: NaOH / tetrahydrofuran; methanol; H₂O / 0 - 20 °C

3: 0.5774 g / dicyclohexylcarbodiimide; 4-dimethylaminopyridine / toluene / 0 - 20 °C

With 2,6-dimethylpyridine; dmap; sodium hydroxide; dicyclohexyl-carbodiimide; In tetrahydrofuran; methanol; dichloromethane; water; toluene;
DOI:10.1021/ol9910058

Reference yield:

: 17407-55-5
(S)-2-Hydroxy-3-methylbutanoic acid

: 250039-51-1
(3S,4R,5S)-4-Benzyloxycarbonylamino-5-methyl-3-triisopropylsilanyloxy-heptanoic acid (S)-1-allyloxycarbonyl-2-methyl-propyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 96 percent / anhydrous potassium carbonate; tetrabutylammonium iodide / dimethylformamide / 1 h / 20 °C

2: 0.5774 g / dicyclohexylcarbodiimide; 4-dimethylaminopyridine / toluene / 0 - 20 °C

With dmap; tetra-(n-butyl)ammonium iodide; potassium carbonate; dicyclohexyl-carbodiimide; In N,N-dimethyl-formamide; toluene;
DOI:10.1021/ol9910058