(+)-amphidinolide A

Base Information

Chemical Name:(+)-amphidinolide A
CAS No.:476452-69-4
Molecular Formula:C₃₁H₄₆O₇
Molecular Weight:530.702
Hs Code.:

Synonyms:

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Chemical Property of (+)-amphidinolide A

Chemical Property:

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Technology Process of (+)-amphidinolide A

There total 36 articles about (+)-amphidinolide A 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: 61.0%

: 476453-09-5
C₄₁H₅₈O₇

: 476452-69-4,424828-97-7
(+)-amphidinolide A

Guidance literature:: With amberlyst-15; In 1,4-dioxane; water; at 60 - 85 ℃; for 66h;
DOI:10.1021/ja053365y

Reference yield:

: (E)-4-(4-Methoxy-benzyloxy)-1-[3-(4-methoxy-benzyloxymethyl)-1,4-dioxa-spiro[4.4]non-2-yl]-but-2-en-1-ol

: 476452-69-4,424828-97-7
(+)-amphidinolide A

Guidance literature:: Multi-step reaction with 17 steps

1.1: Dess-Martin periodinane; sodium bicarbonate / CH₂Cl₂ / 0.5 h / 20 °C

1.2: potassium hexaferricyanide; potassium carbonate; sodium bicarbonate / methanesulfonamide; (DHQD)2-PHAL / 2-methyl-propan-2-ol; H₂O / 24 h / 0 - 3 °C

2.1: 88 percent / p-toluenesulfonic acid hydrate / CH₂Cl₂ / 4 h / 0 °C

3.1: diethyl ether; tetrahydrofuran / 4 h / 20 °C

4.1: 14.8 g / potassium hexamethyldisilazide / tetrahydrofuran; toluene / 18 h / 20 °C

5.1: 83 percent / DDQ / CH₂Cl₂; H₂O / 1.25 h / 20 °C

6.1: sodium hydride / tetrahydrofuran; various solvent(s) / 5 h / 20 °C

6.2: 80 percent / tetrahydrofuran; various solvent(s) / 48 h / 20 °C

7.1: pyridine / CH₂Cl₂ / 0.25 h / -50 °C

7.2: CH₂Cl₂ / 0.67 h / -50 °C

8.1: n-butyllithium / tetrahydrofuran; hexane / 1.5 h / -78 - 0 °C

8.2: DMPU / tetrahydrofuran; hexane / 0.75 h / -78 °C

9.1: 4.13 g / tetrabutylammonium fluoride; acetic acid / tetrahydrofuran / 24 h / 20 °C

10.1: 96 percent / H₂; quinoline / palladium/CaCO₃/Pb / ethyl acetate / 1.5 h / 0 °C / 760.05 Torr

11.1: oxalyl chloride; DMSO; diisopropylethylamine / CH₂Cl₂ / 0.75 h / -78 - -20 °C

12.1: sodium hexamethyldisilazide / tetrahydrofuran / 0.33 h / -78 °C

12.2: 0.578 g / tetrahydrofuran / 0.5 h / -78 °C

13.1: Cp*Ru(MeCN)3PF₆ / 1,2-dichloro-ethane / 2 h / 50 °C

14.1: 85 percent / piperidine / CH₂Cl₂ / 2 h

15.1: ethyl ethynyl ether; [RuCl₂(p-cymene)]2 / toluene; hexane / 2 h

15.2: 66 percent / camphorsulfonic acid / 1,2-dichloro-ethane / 2 h

16.1: 58 percent / CpRu(MeCN)3PF₆ / 1,2-dichloro-ethane / 1 h / 50 °C

17.1: 61 percent / water / dioxane / 60 h / 60 °C

With piperidine; pyridine; quinoline; n-butyllithium; oxalyl dichloride; cyclopentadienylruthenium(II) trisacetonitrile hexafluorophosphate; [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂; tris(acetonitrile)pentamethylcyclopentadienylruthenium(II) hexafluorophosphate; tetrabutyl ammonium fluoride; water; hydrogen; sodium hexamethyldisilazane; potassium hexamethylsilazane; sodium hydride; sodium hydrogencarbonate; Dess-Martin periodane; toluene-4-sulfonic acid; acetic acid; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; 1-ethoxyacetylene; 2,3-dicyano-5,6-dichloro-p-benzoquinone; Lindlar's catalyst; In tetrahydrofuran; 1,4-dioxane; diethyl ether; hexane; dichloromethane; water; ethyl acetate; 1,2-dichloro-ethane; toluene; 1.1: Dess-Martin oxidation / 1.2: Sharpless asymmetric dihydroxylation / 11.1: Moffatt-Swern oxidation;
DOI:10.1021/ja027883+

Reference yield:

: 4-(tert-butyl-dimethyl-silanyloxy)-1,7-bis-(4-methoxy-benzyloxy)-hept-5-ene-2,3-diol

: 476452-69-4,424828-97-7
(+)-amphidinolide A

Guidance literature:: Multi-step reaction with 19 steps

1.1: p-toluenesulfonic acid / CH₂Cl₂ / 1.75 h / 0 °C

2.1: 94 percent / tetrabutylammonium fluoride / tetrahydrofuran / 16 h / 0 - 20 °C

3.1: Dess-Martin periodinane; sodium bicarbonate / CH₂Cl₂ / 0.5 h / 20 °C

3.2: potassium hexaferricyanide; potassium carbonate; sodium bicarbonate / methanesulfonamide; (DHQD)2-PHAL / 2-methyl-propan-2-ol; H₂O / 24 h / 0 - 3 °C

4.1: 88 percent / p-toluenesulfonic acid hydrate / CH₂Cl₂ / 4 h / 0 °C

5.1: diethyl ether; tetrahydrofuran / 4 h / 20 °C

6.1: 14.8 g / potassium hexamethyldisilazide / tetrahydrofuran; toluene / 18 h / 20 °C

7.1: 83 percent / DDQ / CH₂Cl₂; H₂O / 1.25 h / 20 °C

8.1: sodium hydride / tetrahydrofuran; various solvent(s) / 5 h / 20 °C

8.2: 80 percent / tetrahydrofuran; various solvent(s) / 48 h / 20 °C

9.1: pyridine / CH₂Cl₂ / 0.25 h / -50 °C

9.2: CH₂Cl₂ / 0.67 h / -50 °C

10.1: n-butyllithium / tetrahydrofuran; hexane / 1.5 h / -78 - 0 °C

10.2: DMPU / tetrahydrofuran; hexane / 0.75 h / -78 °C

11.1: 4.13 g / tetrabutylammonium fluoride; acetic acid / tetrahydrofuran / 24 h / 20 °C

12.1: 96 percent / H₂; quinoline / palladium/CaCO₃/Pb / ethyl acetate / 1.5 h / 0 °C / 760.05 Torr

13.1: oxalyl chloride; DMSO; diisopropylethylamine / CH₂Cl₂ / 0.75 h / -78 - -20 °C

14.1: sodium hexamethyldisilazide / tetrahydrofuran / 0.33 h / -78 °C

14.2: 0.578 g / tetrahydrofuran / 0.5 h / -78 °C

15.1: Cp*Ru(MeCN)3PF₆ / 1,2-dichloro-ethane / 2 h / 50 °C

16.1: 85 percent / piperidine / CH₂Cl₂ / 2 h

17.1: ethyl ethynyl ether; [RuCl₂(p-cymene)]2 / toluene; hexane / 2 h

17.2: 66 percent / camphorsulfonic acid / 1,2-dichloro-ethane / 2 h

18.1: 58 percent / CpRu(MeCN)3PF₆ / 1,2-dichloro-ethane / 1 h / 50 °C

19.1: 61 percent / water / dioxane / 60 h / 60 °C

With piperidine; pyridine; quinoline; n-butyllithium; oxalyl dichloride; cyclopentadienylruthenium(II) trisacetonitrile hexafluorophosphate; [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂; tris(acetonitrile)pentamethylcyclopentadienylruthenium(II) hexafluorophosphate; tetrabutyl ammonium fluoride; water; hydrogen; sodium hexamethyldisilazane; potassium hexamethylsilazane; sodium hydride; sodium hydrogencarbonate; Dess-Martin periodane; toluene-4-sulfonic acid; acetic acid; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; 1-ethoxyacetylene; 2,3-dicyano-5,6-dichloro-p-benzoquinone; Lindlar's catalyst; In tetrahydrofuran; 1,4-dioxane; diethyl ether; hexane; dichloromethane; water; ethyl acetate; 1,2-dichloro-ethane; toluene; 3.1: Dess-Martin oxidation / 3.2: Sharpless asymmetric dihydroxylation / 13.1: Moffatt-Swern oxidation;
DOI:10.1021/ja027883+