tert-Butyl (3S,4S,5S)-3-hydroxy-4--5-methylheptanoate

Base Information

• Chemical Name: tert-Butyl (3S,4S,5S)-3-hydroxy-4--5-methylheptanoate
• CAS No.: 120205-57-4
• Molecular Formula: C₂₁H₃₃NO₅
• Molecular Weight: 379.497

Synonyms:tert-Butyl (3S,4S,5S)-3-hydroxy-4--5-methylheptanoate

Chemical Property of tert-Butyl (3S,4S,5S)-3-hydroxy-4--5-methylheptanoate

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Technology Process of tert-Butyl (3S,4S,5S)-3-hydroxy-4--5-methylheptanoate

There total 11 articles about tert-Butyl (3S,4S,5S)-3-hydroxy-4--5-methylheptanoate 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: 76.0%

acetic acid tert-butyl ester (540-88-5) + N-Z-N-Me-(S,R)-isoleucinal (120205-56-3,130199-64-3) → tert-butyl 3-hydroxy-4(S)-(N-Z-N-Me)-5(R)-methylheptanoate (120205-57-4,120294-43-1,130273-09-5,130273-14-2)

Guidance literature:

With lithium diisopropyl amide; at -78 ℃;

DOI:10.1021/jm00174a006

Reference yield: 72.0%

(4S,5S)-4-(Benzyloxycarbonyl-methyl-amino)-5-methyl-3-oxo-heptanoic acid tert-butyl ester → tert-Butyl (3S,4S,5S)-3-hydroxy-4--5-methylheptanoate (120205-57-4)

Guidance literature:

With sodium tetrahydroborate; In methanol;

DOI:10.1016/S0040-4039(00)79932-1

Reference yield: 45.0%

acetic acid tert-butyl ester (540-88-5) + benzyl methyl[(2S,3S)-3-methyl-1-oxopentan-2-yl]carbamate (120205-56-3) → tert-Butyl (3S,4S,5S)-3-hydroxy-4--5-methylheptanoate (120205-57-4) + tert-Butyl (3R,4S,5S)-3-hydroxy-4--5-methylheptanoate (120294-43-1)

Guidance literature:

With lithium diisopropyl amide; In tetrahydrofuran; 1.) -20 deg C, 2 h, 2.) -78 deg C, 1 h;

DOI:10.1021/jo00086a034

upstream raw materials:

acetic acid tert-butyl ester

N-Z-N-Me-(S,R)-isoleucinal

N-benzyloxycarbonyl-isoleucine

isoleucine

Downstream raw materials:

tert-Butyl (3S,4S,5S)-3-methoxy-4--5-methylheptanoate

tert-butyl (3R,4S,5S)-4-[(2S)-2-[[(benzyloxy)carbonyl]amino]-N,3-dimethylbutanamido]-3-methoxy-5-methylheptanoate

(3R,4S,5S)-tert-butyl 4-((S)-2-((S)-2-(dimethylamino)-3-methylbutanamido)-N,3-dimethylbutanamido)-3-methoxy-5-methylheptanoate

tert-Butyl (3R,4S,5S)-3-methoxy-4-(N-methylamino)-5-methylheptanoate hydrochloride

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