(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
Hs Code.:

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

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

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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%

: 100-39-0
benzyl bromide

: 752251-00-6
(2S,3S)-3-(3-benzyloxy-2-tert-butoxycarbonylamino-propionylamino)-6,7-dihydroxy-1,1-dimethyl-1,2,3,4-tetrahydro-quinolinium

: 752251-05-1
(2S,3S)-6,7-bis-benzyloxy-3-(3-benzyloxy-2-tert-butoxycarbonylaminopropionylamino)-1,1-dimethyl-1,2,3,4-tetrahydroquinolinium

Guidance literature:: With caesium carbonate; In acetone; for 4h; Heating;
DOI:10.1002/anie.200453909

Reference yield:

: 59-92-7,90638-38-3
levodopa

: 752251-05-1
(2S,3S)-6,7-bis-benzyloxy-3-(3-benzyloxy-2-tert-butoxycarbonylaminopropionylamino)-1,1-dimethyl-1,2,3,4-tetrahydroquinolinium

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

: 752251-05-1
(2S,3S)-6,7-bis-benzyloxy-3-(3-benzyloxy-2-tert-butoxycarbonylaminopropionylamino)-1,1-dimethyl-1,2,3,4-tetrahydroquinolinium

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