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

Base Information

Chemical Name:(2S,3S)-3-(3-benzyloxy-2-tert-butoxycarbonylamino-propionylamino)-6,7-dihydroxy-1,1-dimethyl-1,2,3,4-tetrahydro-quinolinium
CAS No.:752251-00-6
Molecular Formula:C₂₆H₃₆N₃O₆
Molecular Weight:486.588
Hs Code.:

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

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

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

There total 5 articles about (2S,3S)-3-(3-benzyloxy-2-tert-butoxycarbonylamino-propionylamino)-6,7-dihydroxy-1,1-dimethyl-1,2,3,4-tetrahydro-quinolinium 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: 80.0%

: 752251-04-0
(S,S)-{2-benzyloxy-1-[1-(3,4-dihydroxy-benzyl)-2-dimethylamino-ethylcarbamoyl]-ethyl}-carbamic acid tert-butyl ester

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

Guidance literature:: With di-(p-methoxyphenyl)tellurium oxide; In dichloromethane; at 20 ℃; for 2h;
DOI:10.1002/anie.200453909

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 6 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

With 4-methyl-morpholine; sodium hydroxide; borane-THF; di-(p-methoxyphenyl)tellurium oxide; triethylamine; trifluoroacetic acid; isobutyl chloroformate; In tetrahydrofuran; 1,4-dioxane; dichloromethane;
DOI:10.1002/anie.200453909

Reference yield:

: 862695-37-2
4-((S)-2-Amino-3-dimethylamino-propyl)-benzene-1,2-diol

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

Guidance literature:: Multi-step reaction with 2 steps

1.1: i-BuOCOCl; Et₃N / tetrahydrofuran / cooling

1.2: 58 percent / tetrahydrofuran / 3 h / -20 - 10 °C

2.1: 80 percent / dianisyltellurium oxide / CH₂Cl₂ / 2 h / 20 °C

With di-(p-methoxyphenyl)tellurium oxide; triethylamine; isobutyl chloroformate; In tetrahydrofuran; dichloromethane;
DOI:10.1002/anie.200453909