(4R,5R,8R,9R,12R,13S)-13-(4-nitrobenzoyloxy)-5,8:9,12-dioxidotricosa-1,4-olide

Base Information

Chemical Name:(4R,5R,8R,9R,12R,13S)-13-(4-nitrobenzoyloxy)-5,8:9,12-dioxidotricosa-1,4-olide
CAS No.:303053-09-0
Molecular Formula:C₃₀H₄₃NO₈
Molecular Weight:545.673
Hs Code.:

Synonyms:(4R,5R,8R,9R,12R,13S)-13-(4-nitrobenzoyloxy)-5,8:9,12-dioxidotricosa-1,4-olide

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Chemical Property of (4R,5R,8R,9R,12R,13S)-13-(4-nitrobenzoyloxy)-5,8:9,12-dioxidotricosa-1,4-olide

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Technology Process of (4R,5R,8R,9R,12R,13S)-13-(4-nitrobenzoyloxy)-5,8:9,12-dioxidotricosa-1,4-olide

There total 51 articles about (4R,5R,8R,9R,12R,13S)-13-(4-nitrobenzoyloxy)-5,8:9,12-dioxidotricosa-1,4-olide 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: 78.0%

: 172821-65-7
(4R,5R,8R,9R,12R,13R)-13-hydroxy-5,8:9,12-dioxidotricosa-1,4-olide

: 62-23-7
4-nitro-benzoic acid

: 303053-09-0
(4R,5R,8R,9R,12R,13S)-13-(4-nitrobenzoyloxy)-5,8:9,12-dioxidotricosa-1,4-olide

Guidance literature:: With triphenylphosphine; diethylazodicarboxylate; In benzene; at 20 ℃; for 16h;
DOI:10.1021/jo000500a

Reference yield:

: 62992-46-5
1-(tetrahydropyranyloxy)-4-pentyn

: 303053-09-0
(4R,5R,8R,9R,12R,13S)-13-(4-nitrobenzoyloxy)-5,8:9,12-dioxidotricosa-1,4-olide

Guidance literature:: Multi-step reaction with 14 steps

1.1: nBuLi / tetrahydrofuran / 2 h / -78 - 0 °C

2.1: 9.95 g / p-TsOH / methanol; H₂O / 1 h / 20 °C

3.1: 91 percent / I₂; imidazole; PPh₃ / toluene / 2 h / 20 °C

4.1: 99 percent / acetonitrile / 16 h / Heating

5.1: KN(SiMe₃)2 / toluene; tetrahydrofuran / 2 h / -78 - 0 °C

5.2: 95 percent / HMPA / tetrahydrofuran; toluene / 16 h / -78 - -5 °C

6.1: AD-mix-β; MeSO2NH2 / 2-methyl-propan-2-ol; H2O / 16 h / 0 °C

7.1: KOH / H₂O; methanol / 60 °C

8.1: 2.12 g / TsOH / CH₂Cl₂ / 0.5 h / 20 °C

9.1: 68 percent / Re₂O₇; 2,6-lutidine / CH₂Cl₂ / 8 h / 20 °C

10.1: 92 percent / H₂; Et₃N / Lindlar catalyst / hexane; various solvent(s) / 16 h / -10 - -4 °C

11.1: 71 percent / Et₃N / CH₂Cl₂ / 1 h / 0 °C

12.1: 92 percent / AD-mix-β; MeSO2NH2 / 2-methyl-propan-2-ol; H2O / 0 °C

13.1: 81 percent / pyridine / 3 h / Heating

14.1: 78 percent / DEAD; PPh₃ / benzene / 16 h / 20 °C

With pyridine; 1H-imidazole; 2,6-dimethylpyridine; potassium hydroxide; n-butyllithium; methanesulfonamide; AD-mix-β; hydrogen; iodine; potassium hexamethylsilazane; toluene-4-sulfonic acid; rhenium(VII) oxide; triethylamine; triphenylphosphine; diethylazodicarboxylate; Lindlar's catalyst; In tetrahydrofuran; methanol; hexane; dichloromethane; water; toluene; acetonitrile; tert-butyl alcohol; benzene; 1.1: Metallation / 2.1: Hydrolysis / 3.1: Substitution / 4.1: Substitution / 5.1: deprotonation / 5.2: Wittig reaction / 6.1: Sharpless hydroxylation / 7.1: Hydrolysis / 8.1: Cyclization / 9.1: Kennedy oxidative cyclization / 10.1: Catalytic hydrogenation / 11.1: Substitution / 12.1: Sharpless asymmetric dihydroxylation / 13.1: Williamson etherification / 14.1: Acylation;
DOI:10.1021/jo000500a

Reference yield:

: 5390-04-5
pent-1-yn-5-ol

: 303053-09-0
(4R,5R,8R,9R,12R,13S)-13-(4-nitrobenzoyloxy)-5,8:9,12-dioxidotricosa-1,4-olide

Guidance literature:: Multi-step reaction with 15 steps

1.1: 96 percent / p-TsOH / diethyl ether / 2 h / 20 °C

2.1: nBuLi / tetrahydrofuran / 2 h / -78 - 0 °C

3.1: 9.95 g / p-TsOH / methanol; H₂O / 1 h / 20 °C

4.1: 91 percent / I₂; imidazole; PPh₃ / toluene / 2 h / 20 °C

5.1: 99 percent / acetonitrile / 16 h / Heating

6.1: KN(SiMe₃)2 / toluene; tetrahydrofuran / 2 h / -78 - 0 °C

6.2: 95 percent / HMPA / tetrahydrofuran; toluene / 16 h / -78 - -5 °C

7.1: AD-mix-β; MeSO2NH2 / 2-methyl-propan-2-ol; H2O / 16 h / 0 °C

8.1: KOH / H₂O; methanol / 60 °C

9.1: 2.12 g / TsOH / CH₂Cl₂ / 0.5 h / 20 °C

10.1: 68 percent / Re₂O₇; 2,6-lutidine / CH₂Cl₂ / 8 h / 20 °C

11.1: 92 percent / H₂; Et₃N / Lindlar catalyst / hexane; various solvent(s) / 16 h / -10 - -4 °C

12.1: 71 percent / Et₃N / CH₂Cl₂ / 1 h / 0 °C

13.1: 92 percent / AD-mix-β; MeSO2NH2 / 2-methyl-propan-2-ol; H2O / 0 °C

14.1: 81 percent / pyridine / 3 h / Heating

15.1: 78 percent / DEAD; PPh₃ / benzene / 16 h / 20 °C

With pyridine; 1H-imidazole; 2,6-dimethylpyridine; potassium hydroxide; n-butyllithium; methanesulfonamide; AD-mix-β; hydrogen; iodine; potassium hexamethylsilazane; toluene-4-sulfonic acid; rhenium(VII) oxide; triethylamine; triphenylphosphine; diethylazodicarboxylate; Lindlar's catalyst; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; toluene; acetonitrile; tert-butyl alcohol; benzene; 1.1: protection / 2.1: Metallation / 3.1: Hydrolysis / 4.1: Substitution / 5.1: Substitution / 6.1: deprotonation / 6.2: Wittig reaction / 7.1: Sharpless hydroxylation / 8.1: Hydrolysis / 9.1: Cyclization / 10.1: Kennedy oxidative cyclization / 11.1: Catalytic hydrogenation / 12.1: Substitution / 13.1: Sharpless asymmetric dihydroxylation / 14.1: Williamson etherification / 15.1: Acylation;
DOI:10.1021/jo000500a