(3R,4S,5S)-4-(N-((2S)-((2S)-N-benzyloxycarbonylamino-3-methylbutanoyl)-3-methylbutanoyl)-N-methylamino)-3-methoxy-5-methylheptanoic acid

Base Information

Chemical Name:(3R,4S,5S)-4-(N-((2S)-((2S)-N-benzyloxycarbonylamino-3-methylbutanoyl)-3-methylbutanoyl)-N-methylamino)-3-methoxy-5-methylheptanoic acid
CAS No.:716371-64-1
Molecular Formula:C₂₈H₄₅N₃O₇
Molecular Weight:535.681
Hs Code.:

Synonyms:(3R,4S,5S)-4-(N-((2S)-((2S)-N-benzyloxycarbonylamino-3-methylbutanoyl)-3-methylbutanoyl)-N-methylamino)-3-methoxy-5-methylheptanoic acid

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Chemical Property of (3R,4S,5S)-4-(N-((2S)-((2S)-N-benzyloxycarbonylamino-3-methylbutanoyl)-3-methylbutanoyl)-N-methylamino)-3-methoxy-5-methylheptanoic acid

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Technology Process of (3R,4S,5S)-4-(N-((2S)-((2S)-N-benzyloxycarbonylamino-3-methylbutanoyl)-3-methylbutanoyl)-N-methylamino)-3-methoxy-5-methylheptanoic acid

There total 17 articles about (3R,4S,5S)-4-(N-((2S)-((2S)-N-benzyloxycarbonylamino-3-methylbutanoyl)-3-methylbutanoyl)-N-methylamino)-3-methoxy-5-methylheptanoic 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: 63.0%

: [(S)-1-((S)-1-{[(1S,2R)-1-((S)-sec-Butyl)-4-((1R,2R,4R)-2-hydroxy-1,7,7-trimethyl-bicyclo[2.2.1]hept-2-yl)-2-methoxy-4-oxo-butyl]-methyl-carbamoyl}-2-methyl-propylcarbamoyl)-2-methyl-propyl]-carbamic acid benzyl ester

: 716371-64-1
(3R,4S,5S)-4-(N-((2S)-((2S)-N-benzyloxycarbonylamino-3-methylbutanoyl)-3-methylbutanoyl)-N-methylamino)-3-methoxy-5-methylheptanoic acid

Guidance literature:: With ammonium cerium(IV) nitrate; In water; acetonitrile; at 0 ℃; for 0.0833333h;
DOI:10.1021/jo0497499

Reference yield:

: 1149-26-4
(S)-N-(benzyloxycarbonyl)valine

: 716371-64-1
(3R,4S,5S)-4-(N-((2S)-((2S)-N-benzyloxycarbonylamino-3-methylbutanoyl)-3-methylbutanoyl)-N-methylamino)-3-methoxy-5-methylheptanoic acid

Guidance literature:: Multi-step reaction with 5 steps

1: 81 percent / diisopropylethylamine; bromotris(dimethylamino)phosphonium hexafluorophosphate / CH₂Cl₂ / 24 h / 20 °C

2: 99 percent / H₂ / Pd/C / ethyl acetate / 25 °C / balloon

3: 60 percent / diisopropylethylamine; bromotris(dimethylamino)phosphonium hexafluorophosphate / CH₂Cl₂ / 24 h / 20 °C

4: HF / H₂O; methanol / 6 h / 20 °C

5: 63 percent / cerium(IV) ammonium nitrate / H₂O; acetonitrile / 0.08 h / 0 °C

With bromo-tris-dimethylamino-phosphonium hexafluorophosphate; ammonium cerium(IV) nitrate; hydrogen fluoride; hydrogen; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In methanol; dichloromethane; water; ethyl acetate; acetonitrile;
DOI:10.1021/jo0497499

Reference yield:

: 120205-56-3
benzyl methyl[(2S,3S)-3-methyl-1-oxopentan-2-yl]carbamate

: 716371-64-1
(3R,4S,5S)-4-(N-((2S)-((2S)-N-benzyloxycarbonylamino-3-methylbutanoyl)-3-methylbutanoyl)-N-methylamino)-3-methoxy-5-methylheptanoic acid

Guidance literature:: Multi-step reaction with 8 steps

1.1: n-butyllithium / hexane; tetrahydrofuran / 1 h / -78 °C

1.2: 75 percent / hexane; tetrahydrofuran / 0.5 h / -78 °C

2.1: 75 percent / molecular sieves 4 Angstroem / CH₂Cl₂ / 24 h / 20 °C

3.1: 99 percent / H₂ / Pd/C / ethyl acetate / 25 °C / balloon

4.1: 81 percent / diisopropylethylamine; bromotris(dimethylamino)phosphonium hexafluorophosphate / CH₂Cl₂ / 24 h / 20 °C

5.1: 99 percent / H₂ / Pd/C / ethyl acetate / 25 °C / balloon

6.1: 60 percent / diisopropylethylamine; bromotris(dimethylamino)phosphonium hexafluorophosphate / CH₂Cl₂ / 24 h / 20 °C

7.1: HF / H₂O; methanol / 6 h / 20 °C

8.1: 63 percent / cerium(IV) ammonium nitrate / H₂O; acetonitrile / 0.08 h / 0 °C

With n-butyllithium; bromo-tris-dimethylamino-phosphonium hexafluorophosphate; ammonium cerium(IV) nitrate; 4 A molecular sieve; hydrogen fluoride; hydrogen; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; hexane; dichloromethane; water; ethyl acetate; acetonitrile;
DOI:10.1021/jo0497499