(R)-2-benzyl-[N-(benzyloxycarbonyl)glycyl]-[N'-(tert-butoxycarbonyl)-D-alanyl]-1,3-propanediamine

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Chemical Name:(R)-2-benzyl-[N-(benzyloxycarbonyl)glycyl]-[N'-(tert-butoxycarbonyl)-D-alanyl]-1,3-propanediamine
CAS No.:254990-90-4
Molecular Formula:C₂₈H₃₈N₄O₆
Molecular Weight:526.633
Hs Code.:

Synonyms:(R)-2-benzyl-[N-(benzyloxycarbonyl)glycyl]-[N'-(tert-butoxycarbonyl)-D-alanyl]-1,3-propanediamine

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Chemical Property of (R)-2-benzyl-[N-(benzyloxycarbonyl)glycyl]-[N'-(tert-butoxycarbonyl)-D-alanyl]-1,3-propanediamine

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Technology Process of (R)-2-benzyl-[N-(benzyloxycarbonyl)glycyl]-[N'-(tert-butoxycarbonyl)-D-alanyl]-1,3-propanediamine

There total 11 articles about (R)-2-benzyl-[N-(benzyloxycarbonyl)glycyl]-[N'-(tert-butoxycarbonyl)-D-alanyl]-1,3-propanediamine 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: 83.0%

: 1138-80-3
N-(Benzyloxycarbonyl)glycine

: [(R)-1-((R)-2-Aminomethyl-3-phenyl-propylcarbamoyl)-ethyl]-carbamic acid tert-butyl ester

: 254990-90-4
(R)-2-benzyl-[N-(benzyloxycarbonyl)glycyl]-[N'-(tert-butoxycarbonyl)-D-alanyl]-1,3-propanediamine

Guidance literature:: With 4-methyl-morpholine; (benzotriazolyl-1-oxy)tripyrrolidinophospho. hexafluorophosp; In dichloromethane; at 0 ℃;
DOI:10.1016/S0957-4166(99)00371-7

Reference yield:

: 2612-30-8
2-benzyl-1,3-propanediol

: 254990-90-4
(R)-2-benzyl-[N-(benzyloxycarbonyl)glycyl]-[N'-(tert-butoxycarbonyl)-D-alanyl]-1,3-propanediamine

Guidance literature:: Multi-step reaction with 12 steps

1: 95 percent / 3A molecular sieves; lipase Amono P supported on Celite / various solvent(s) / 5.7 h / 25 °C

2: Et₃N / CH₂Cl₂ / 2.5 h / -30 °C

3: 96 percent / sodium azide / dimethylformamide / 50 °C

4: 99 percent / pH 7 buffer; lipase Amano P / 22 h / 20 °C / pH 7

5: 94 percent / H₂O, PPh₃ / tetrahydrofuran / 6 h / 50 °C

6: 94 percent / 6N aq. NaOH / 0.17 h / 0 °C / pH 9

7: Et₃N / CH₂Cl₂ / -30 °C

8: 92 percent / sodium azide / dimethylformamide / 50 °C

9: 98 percent / H₂O; PPh₃ / tetrahydrofuran / 6 h / 50 °C

10: 85 percent / (benzotriazolyl-1-oxy)tripyrrolidinophospho. hexafluorophosp; 4-methylmorpholine / CH₂Cl₂ / 0 °C

11: H₂ / 10 percent Pd/C / methanol / 0.5 h / 760 Torr

12: 83 percent / (benzotriazolyl-1-oxy)tripyrrolidinophospho. hexafluorophosp; 4-methylmorpholine / CH₂Cl₂ / 0 °C

With 4-methyl-morpholine; sodium hydroxide; sodium azide; (benzotriazolyl-1-oxy)tripyrrolidinophospho. hexafluorophosp; 3 A molecular sieve; lipase Amano P; lipase Amono P supported on Celite; pH 7 buffer; water; hydrogen; triethylamine; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; 1: Acylation / 2: mesylation / 3: Substitution / 4: Hydrolysis / 5: Staudinger reaction / 6: Acylation / 7: Substitution / 8: Substitution / 9: Staudinger reaction / 10: Acylation / 11: Reduction / 12: Acylation;
DOI:10.1016/S0957-4166(99)00371-7

Reference yield:

: 110270-49-0
(R)-3-acetoxy-2-benzyl-1-propanol

: 254990-90-4
(R)-2-benzyl-[N-(benzyloxycarbonyl)glycyl]-[N'-(tert-butoxycarbonyl)-D-alanyl]-1,3-propanediamine

Guidance literature:: Multi-step reaction with 11 steps

1: Et₃N / CH₂Cl₂ / 2.5 h / -30 °C

2: 96 percent / sodium azide / dimethylformamide / 50 °C

3: 99 percent / pH 7 buffer; lipase Amano P / 22 h / 20 °C / pH 7

4: 94 percent / H₂O, PPh₃ / tetrahydrofuran / 6 h / 50 °C

5: 94 percent / 6N aq. NaOH / 0.17 h / 0 °C / pH 9

6: Et₃N / CH₂Cl₂ / -30 °C

7: 92 percent / sodium azide / dimethylformamide / 50 °C

8: 98 percent / H₂O; PPh₃ / tetrahydrofuran / 6 h / 50 °C

9: 85 percent / (benzotriazolyl-1-oxy)tripyrrolidinophospho. hexafluorophosp; 4-methylmorpholine / CH₂Cl₂ / 0 °C

10: H₂ / 10 percent Pd/C / methanol / 0.5 h / 760 Torr

11: 83 percent / (benzotriazolyl-1-oxy)tripyrrolidinophospho. hexafluorophosp; 4-methylmorpholine / CH₂Cl₂ / 0 °C

With 4-methyl-morpholine; sodium hydroxide; sodium azide; (benzotriazolyl-1-oxy)tripyrrolidinophospho. hexafluorophosp; lipase Amano P; pH 7 buffer; water; hydrogen; triethylamine; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; 1: mesylation / 2: Substitution / 3: Hydrolysis / 4: Staudinger reaction / 5: Acylation / 6: Substitution / 7: Substitution / 8: Staudinger reaction / 9: Acylation / 10: Reduction / 11: Acylation;
DOI:10.1016/S0957-4166(99)00371-7