(3R,4S)-tert-butyl 4-((benzyloxycarbonyl)(methyl)amino)-3-hydroxy-5-methylhexanoate

Base Information

Chemical Name:(3R,4S)-tert-butyl 4-((benzyloxycarbonyl)(methyl)amino)-3-hydroxy-5-methylhexanoate
CAS No.:1611479-63-0
Molecular Formula:C₂₀H₃₁NO₅
Molecular Weight:365.47
Hs Code.:

Synonyms:(3R,4S)-tert-butyl 4-((benzyloxycarbonyl)(methyl)amino)-3-hydroxy-5-methylhexanoate

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Chemical Property of (3R,4S)-tert-butyl 4-((benzyloxycarbonyl)(methyl)amino)-3-hydroxy-5-methylhexanoate

Chemical Property:

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Technology Process of (3R,4S)-tert-butyl 4-((benzyloxycarbonyl)(methyl)amino)-3-hydroxy-5-methylhexanoate

There total 2 articles about (3R,4S)-tert-butyl 4-((benzyloxycarbonyl)(methyl)amino)-3-hydroxy-5-methylhexanoate 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: 37.0%

: 540-88-5
acetic acid tert-butyl ester

: 149357-30-2
(S)-benzyl methyl(3-methyl-1-oxobutan-2-yl)carbamate

: 1611479-87-8
(3S,4S)-tert-butyl 4-((benzyloxycarbonyl)(methyl)amino)-3-hydroxy-5-methylhexanoate

: 1611479-63-0
(3R,4S)-tert-butyl 4-((benzyloxycarbonyl)(methyl)amino)-3-hydroxy-5-methylhexanoate

Guidance literature:: acetic acid tert-butyl ester; With lithium diisopropyl amide; In tetrahydrofuran; hexane; at -78 ℃; for 2h;

(S)-benzyl methyl(3-methyl-1-oxobutan-2-yl)carbamate; In tetrahydrofuran; hexane; at -78 ℃; for 1h;
DOI:10.3762/bjoc.10.29

Reference yield:

: N-Cbz-N-methylvalinol

: 1611479-87-8
(3S,4S)-tert-butyl 4-((benzyloxycarbonyl)(methyl)amino)-3-hydroxy-5-methylhexanoate

: 1611479-63-0
(3R,4S)-tert-butyl 4-((benzyloxycarbonyl)(methyl)amino)-3-hydroxy-5-methylhexanoate

Guidance literature:: Multi-step reaction with 2 steps

1.1: triethylamine / dimethyl sulfoxide / 0.25 h / 20 °C / Inert atmosphere

1.2: 0.83 h / 0 °C / Inert atmosphere

2.1: lithium diisopropyl amide / tetrahydrofuran; hexane / 2 h / -78 °C

2.2: 1 h / -78 °C

With triethylamine; lithium diisopropyl amide; In tetrahydrofuran; hexane; dimethyl sulfoxide; 1.1: |Parikh-Doering Oxidation;
DOI:10.3762/bjoc.10.29

Reference yield: 87.0%

: 1611479-63-0
(3R,4S)-tert-butyl 4-((benzyloxycarbonyl)(methyl)amino)-3-hydroxy-5-methylhexanoate

: 420-37-1
trimethoxonium tetrafluoroborate

: 149606-47-3
(3R,4S)-tert-butyl 4-((benzyloxycarbonyl)(methyl)amino)-3-methoxy-5-methylhexanoate

Guidance literature:: With N,N,N',N'-tetramethyl-1,8-diaminonaphthalene; In 1,2-dichloro-ethane; at 0 - 20 ℃; for 18h; Inert atmosphere; Molecular sieve;
DOI:10.3762/bjoc.10.29