N-[1-(2'-azido-1'(R)-hydroxy-1(R)-methyl)butylcarboxy]-L-phenylalanyl-L-leucyl methyl ester

Base Information

Chemical Name:N-[1-(2'-azido-1'(R)-hydroxy-1(R)-methyl)butylcarboxy]-L-phenylalanyl-L-leucyl methyl ester
CAS No.:264921-79-1
Molecular Formula:C₂₂H₃₃N₅O₅
Molecular Weight:447.535
Hs Code.:

Synonyms:N-[1-(2'-azido-1'(R)-hydroxy-1(R)-methyl)butylcarboxy]-L-phenylalanyl-L-leucyl methyl ester

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Chemical Property of N-[1-(2'-azido-1'(R)-hydroxy-1(R)-methyl)butylcarboxy]-L-phenylalanyl-L-leucyl methyl ester

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Technology Process of N-[1-(2'-azido-1'(R)-hydroxy-1(R)-methyl)butylcarboxy]-L-phenylalanyl-L-leucyl methyl ester

There total 8 articles about N-[1-(2'-azido-1'(R)-hydroxy-1(R)-methyl)butylcarboxy]-L-phenylalanyl-L-leucyl methyl 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: 93.0%

: 186581-53-3,908094-01-9,334-88-3
diazomethane

: 264921-78-0
N-[1-(2'-azido-1'(R)-hydroxy-1(R)-methyl)butylcarboxy]-L-phenylalanyl-L-leucine

: 264921-79-1
N-[1-(2'-azido-1'(R)-hydroxy-1(R)-methyl)butylcarboxy]-L-phenylalanyl-L-leucyl methyl ester

Guidance literature:: In diethyl ether;
DOI:10.1021/jo991288h

Reference yield:

: 78158-90-4
(5R)-5-<(triphenylmethoxy)methyl>-γ-butyrolactone

: 264921-79-1
N-[1-(2'-azido-1'(R)-hydroxy-1(R)-methyl)butylcarboxy]-L-phenylalanyl-L-leucyl methyl ester

Guidance literature:: Multi-step reaction with 7 steps

1.1: (i-Pr)2NLi / tetrahydrofuran / 0.5 h / -78 °C

1.2: tetrahydrofuran / 3.5 h / -78 - -40 °C

2.1: LDA / tetrahydrofuran / 1 h / -78 °C

2.2: 70 percent / Na₂SO₄; H₂O / tetrahydrofuran / -78 - 0 °C

3.1: 87 percent / HCl / methanol / 2 h / 20 °C

4.1: 91 percent / Et₃N; DMAP / CH₂Cl₂ / 14 h / 20 °C

5.1: 82 percent / NaN₃ / dimethylformamide / 5 h / 65 °C

6.1: 70 percent / Me₃Al / hexane; 1,2-dichloro-ethane / 24 h / Heating

7.1: 93 percent / diethyl ether

With hydrogenchloride; dmap; sodium azide; trimethylaluminum; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide; 1.1: Alkylation / 1.2: Alkylation / 2.1: Isomerization / 2.2: Hydrolysis / 3.1: Hydrolysis / 4.1: Tosylation / 5.1: Substitution / 6.1: Ring cleavage / 7.1: Esterification;
DOI:10.1021/jo991288h

Reference yield:

: 3303-55-7
L-Phe-Leu

: 264921-79-1
N-[1-(2'-azido-1'(R)-hydroxy-1(R)-methyl)butylcarboxy]-L-phenylalanyl-L-leucyl methyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 70 percent / Me₃Al / hexane; 1,2-dichloro-ethane / 24 h / Heating

2: 93 percent / diethyl ether

With trimethylaluminum; In diethyl ether; hexane; 1,2-dichloro-ethane; 1: Ring cleavage / 2: Esterification;
DOI:10.1021/jo991288h