(2S,3S)-6,7-bis-benzyloxy-3-(3-benzyloxy-2-tert-butoxycarbonylaminopropionylamino)-1,1-dimethyl-1,2,3,4-tetrahydroquinolinium

Base Information

• Chemical Name: (2S,3S)-6,7-bis-benzyloxy-3-(3-benzyloxy-2-tert-butoxycarbonylaminopropionylamino)-1,1-dimethyl-1,2,3,4-tetrahydroquinolinium
• CAS No.: 752251-05-1
• Molecular Formula: C₄₀H₄₈N₃O₆
• Molecular Weight: 666.838
• Mol file: 752251-05-1.mol

Synonyms:(2S,3S)-6,7-bis-benzyloxy-3-(3-benzyloxy-2-tert-butoxycarbonylaminopropionylamino)-1,1-dimethyl-1,2,3,4-tetrahydroquinolinium

Chemical Property of (2S,3S)-6,7-bis-benzyloxy-3-(3-benzyloxy-2-tert-butoxycarbonylaminopropionylamino)-1,1-dimethyl-1,2,3,4-tetrahydroquinolinium

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S)-6,7-bis-benzyloxy-3-(3-benzyloxy-2-tert-butoxycarbonylaminopropionylamino)-1,1-dimethyl-1,2,3,4-tetrahydroquinolinium

There total 7 articles about (2S,3S)-6,7-bis-benzyloxy-3-(3-benzyloxy-2-tert-butoxycarbonylaminopropionylamino)-1,1-dimethyl-1,2,3,4-tetrahydroquinolinium 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: 85.0%

benzyl bromide (100-39-0) + (2S,3S)-3-(3-benzyloxy-2-tert-butoxycarbonylamino-propionylamino)-6,7-dihydroxy-1,1-dimethyl-1,2,3,4-tetrahydro-quinolinium (752251-00-6) → (2S,3S)-6,7-bis-benzyloxy-3-(3-benzyloxy-2-tert-butoxycarbonylaminopropionylamino)-1,1-dimethyl-1,2,3,4-tetrahydroquinolinium (752251-05-1)

Guidance literature:

With caesium carbonate; In acetone; for 4h; Heating;

DOI:10.1002/anie.200453909

Reference yield:

levodopa (59-92-7,90638-38-3) → (2S,3S)-6,7-bis-benzyloxy-3-(3-benzyloxy-2-tert-butoxycarbonylaminopropionylamino)-1,1-dimethyl-1,2,3,4-tetrahydroquinolinium (752251-05-1)

Guidance literature:

Multi-step reaction with 7 steps

1.1: aq. NaOH / dioxane / 16 h / 20 °C

2.1: i-BuOCOCl; N-methylmorpholine / tetrahydrofuran / 0.5 h / -35 °C

2.2: 5.0 g / tetrahydrofuran / 20 °C

3.1: TFA / CH₂Cl₂ / 2 h / 0 - 20 °C

4.1: BH₃*THF / tetrahydrofuran / 0 - 20 °C

5.1: i-BuOCOCl; Et₃N / tetrahydrofuran / cooling

5.2: 58 percent / tetrahydrofuran / 3 h / -20 - 10 °C

6.1: 80 percent / dianisyltellurium oxide / CH₂Cl₂ / 2 h / 20 °C

7.1: 85 percent / Cs₂CO₃ / acetone / 4 h / Heating

With 4-methyl-morpholine; sodium hydroxide; borane-THF; di-(p-methoxyphenyl)tellurium oxide; caesium carbonate; triethylamine; trifluoroacetic acid; isobutyl chloroformate; In tetrahydrofuran; 1,4-dioxane; dichloromethane; acetone;

DOI:10.1002/anie.200453909

Reference yield:

2-amino-3-(3,4-dihydroxy-phenyl)-N,N-dimethyl-propionamide → (2S,3S)-6,7-bis-benzyloxy-3-(3-benzyloxy-2-tert-butoxycarbonylaminopropionylamino)-1,1-dimethyl-1,2,3,4-tetrahydroquinolinium (752251-05-1)

Guidance literature:

Multi-step reaction with 4 steps

1.1: BH₃*THF / tetrahydrofuran / 0 - 20 °C

2.1: i-BuOCOCl; Et₃N / tetrahydrofuran / cooling

2.2: 58 percent / tetrahydrofuran / 3 h / -20 - 10 °C

3.1: 80 percent / dianisyltellurium oxide / CH₂Cl₂ / 2 h / 20 °C

4.1: 85 percent / Cs₂CO₃ / acetone / 4 h / Heating

With borane-THF; di-(p-methoxyphenyl)tellurium oxide; caesium carbonate; triethylamine; isobutyl chloroformate; In tetrahydrofuran; dichloromethane; acetone;

DOI:10.1002/anie.200453909

upstream raw materials:

benzyl bromide

(2S,3S)-3-(3-benzyloxy-2-tert-butoxycarbonylamino-propionylamino)-6,7-dihydroxy-1,1-dimethyl-1,2,3,4-tetrahydro-quinolinium

levodopa

4-((S)-2-Amino-3-dimethylamino-propyl)-benzene-1,2-diol

Downstream raw materials:

(S)-3-amino-6,7-bis(OBn)-1,1-dimethyl-1,2,3,4-tetrahydroquinolin-1-ium L-ser(OBn)-D-ser (OBn)-BocL-thr(OBn)

H-L-Thr(OBn)-D-Ser(OBn)-LSer(OBn)-(3S)-THQ(OBn)

(S)-3-((S)-2-Amino-3-benzyloxy-propionylamino)-6,7-bis-benzyloxy-1,1-dimethyl-1,2,3,4-tetrahydro-quinolinium