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

Base Information

Chemical Name:N-[1-(2'-azido-1'(R)-hydroxy-1(R)-methyl)butylcarboxy]-L-phenylalanyl-L-leucine
CAS No.:264921-78-0
Molecular Formula:C₂₁H₃₁N₅O₅
Molecular Weight:433.508
Hs Code.:

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

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

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

There total 6 articles about N-[1-(2'-azido-1'(R)-hydroxy-1(R)-methyl)butylcarboxy]-L-phenylalanyl-L-leucine 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: 70.0%

: 3303-55-7
L-Phe-Leu

: 147093-46-7
(R)-(-)-γ-azidomethyl-[2(R)-methyl]-γ-butyrolactone

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

Guidance literature:: With trimethylaluminum; In hexane; 1,2-dichloro-ethane; for 24h; Heating;
DOI:10.1021/jo991288h

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 6 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

With hydrogenchloride; dmap; sodium azide; trimethylaluminum; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; methanol; 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;
DOI:10.1021/jo991288h

Reference yield:

: 147200-11-1
(R)-(-)-γ-hydroxymethyl-[2(R)-methyl]-γ-butyrolactone

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

Guidance literature:: Multi-step reaction with 3 steps

1: 91 percent / Et₃N; DMAP / CH₂Cl₂ / 14 h / 20 °C

2: 82 percent / NaN₃ / dimethylformamide / 5 h / 65 °C

3: 70 percent / Me₃Al / hexane; 1,2-dichloro-ethane / 24 h / Heating

With dmap; sodium azide; trimethylaluminum; triethylamine; In hexane; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide; 1: Tosylation / 2: Substitution / 3: Ring cleavage;
DOI:10.1021/jo991288h