1-Oxa-3,9-diazacyclopentadecane-8,12-dicarboxylic acid, 11-[(4-hydroxyphenyl)methyl]-2,10-dioxo-, 12-(1,1-dimethylethyl) 8-methyl ester, (8S,11R,12S)-

Base Information

Chemical Name:1-Oxa-3,9-diazacyclopentadecane-8,12-dicarboxylic acid, 11-[(4-hydroxyphenyl)methyl]-2,10-dioxo-, 12-(1,1-dimethylethyl) 8-methyl ester, (8S,11R,12S)-
CAS No.:377088-79-4
Molecular Formula:C26H38N2O8
Molecular Weight:506.596
Hs Code.:

1-Oxa-3,9-diazacyclopentadecane-8,12-dicarboxylic acid,
11-[(4-hydroxyphenyl)methyl]-2,10-dioxo-, 12-(1,1-dimethylethyl)
8-methyl ester, (8S,11R,12S)-

Synonyms:

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Chemical Property of 1-Oxa-3,9-diazacyclopentadecane-8,12-dicarboxylic acid, 11-[(4-hydroxyphenyl)methyl]-2,10-dioxo-, 12-(1,1-dimethylethyl) 8-methyl ester, (8S,11R,12S)-

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Technology Process of 1-Oxa-3,9-diazacyclopentadecane-8,12-dicarboxylic acid, 11-[(4-hydroxyphenyl)methyl]-2,10-dioxo-, 12-(1,1-dimethylethyl) 8-methyl ester, (8S,11R,12S)-

There total 13 articles about 1-Oxa-3,9-diazacyclopentadecane-8,12-dicarboxylic acid, 11-[(4-hydroxyphenyl)methyl]-2,10-dioxo-, 12-(1,1-dimethylethyl) 8-methyl ester, (8S,11R,12S)- 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: 94.0%

: (2R,3S)-2-[3-((S)-5-Carboxyamino-5-methoxycarbonyl-pentylcarbamoyloxy)-propyl]-3-(4-hydroxy-benzyl)-succinic acid 1-tert-butyl ester

: 377088-79-4
12-tert-butyl-8-methyl(8S,11R,12S)-11-(4-hydroxybenzyl)-2,10-dioxo-1-oxa-3,9-diazacyclopentadecane-8,12-dicarboxylate

Guidance literature:: With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In chloroform; N,N-dimethyl-formamide; at 20 ℃;
DOI:10.1021/jm0155502

Reference yield:

: 5597-50-2
3-(4-hydroxyphenyl)propionic acid methyl ester

: 377088-79-4
12-tert-butyl-8-methyl(8S,11R,12S)-11-(4-hydroxybenzyl)-2,10-dioxo-1-oxa-3,9-diazacyclopentadecane-8,12-dicarboxylate

Guidance literature:: Multi-step reaction with 12 steps

1.1: 76 percent / K₂CO₃ / dimethylformamide / 3 h / 80 °C

2.1: 98 percent / LiOH; H₂O / tetrahydrofuran / 2 h / 20 °C

3.1: pivaloyl chloride; DIEA / tetrahydrofuran / 1 h / -30 °C

3.2: 60 percent / LiCl / tetrahydrofuran / -30 - 20 °C

4.1: diisopropylamine; n-BuLi / tetrahydrofuran / 1 h / -78 °C

4.2: 61 percent / tetrahydrofuran / -78 - 0 °C

5.1: 100 percent / LiOH; H₂O₂ / tetrahydrofuran; H₂O / 3 h / 0 °C

6.1: LDA / tetrahydrofuran / 1 h / -78 °C

6.2: 84 percent / tetrahydrofuran / 0 - 5 °C

7.1: LDA; Et₂AlCl / tetrahydrofuran / -78 - 20 °C

7.2: 7.69 g / DBU / benzene / 50 °C

8.1: 9-BBN / tetrahydrofuran / 20 °C

8.2: 87 percent / NaOAc; H₂O₂ / tetrahydrofuran; H₂O / 0 °C

9.1: 78 percent / NMM / CH₂Cl₂ / 3 h / 20 °C

10.1: 81 percent / K₂CO₃ / dimethylformamide / 2 h / 50 °C

11.1: 93 percent / H₂ / Pd/C / methanol / 2 h

12.1: 94 percent / BOP; DIEA / CHCl₃; dimethylformamide / 20 °C

With 4-methyl-morpholine; lithium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; n-butyllithium; water; hydrogen; dihydrogen peroxide; diethylaluminium chloride; pivaloyl chloride; potassium carbonate; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; diisopropylamine; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; chloroform; water; N,N-dimethyl-formamide;
DOI:10.1021/jm0155502

Reference yield:

: (2R,3R)-2-Allyl-3-(4-benzyloxy-benzyl)-succinic acid 1-tert-butyl ester

: 377088-79-4
12-tert-butyl-8-methyl(8S,11R,12S)-11-(4-hydroxybenzyl)-2,10-dioxo-1-oxa-3,9-diazacyclopentadecane-8,12-dicarboxylate

Guidance literature:: Multi-step reaction with 6 steps

1.1: LDA; Et₂AlCl / tetrahydrofuran / -78 - 20 °C

1.2: 7.69 g / DBU / benzene / 50 °C

2.1: 9-BBN / tetrahydrofuran / 20 °C

2.2: 87 percent / NaOAc; H₂O₂ / tetrahydrofuran; H₂O / 0 °C

3.1: 78 percent / NMM / CH₂Cl₂ / 3 h / 20 °C

4.1: 81 percent / K₂CO₃ / dimethylformamide / 2 h / 50 °C

5.1: 93 percent / H₂ / Pd/C / methanol / 2 h

6.1: 94 percent / BOP; DIEA / CHCl₃; dimethylformamide / 20 °C

With 4-methyl-morpholine; 9-borabicyclo[3.3.1]nonane dimer; hydrogen; diethylaluminium chloride; potassium carbonate; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; chloroform; N,N-dimethyl-formamide;
DOI:10.1021/jm0155502