(5S,9S)-5-[(S)-2-Furan-3-yl-2-(4-methoxy-benzyloxy)-ethyl]-9-hydroxy-6-oxo-3-(2-oxo-propyl)-4,5,6,7,8,9-hexahydro-cycloocta[c]furan-5-carboxylic acid methyl ester

Base Information

Chemical Name:(5S,9S)-5-[(S)-2-Furan-3-yl-2-(4-methoxy-benzyloxy)-ethyl]-9-hydroxy-6-oxo-3-(2-oxo-propyl)-4,5,6,7,8,9-hexahydro-cycloocta[c]furan-5-carboxylic acid methyl ester
CAS No.:304457-17-8
Molecular Formula:C₂₉H₃₂O₉
Molecular Weight:524.568
Hs Code.:

(5S,9S)-5-[(S)-2-Furan-3-yl-2-(4-methoxy-benzyloxy)-ethyl]-9-hydroxy-6-oxo-3-(2-oxo-propyl)-4,5,6,7,8,9-hexahydro-cycloocta[c]furan-5-carboxylic acid methyl ester

Synonyms:(5S,9S)-5-[(S)-2-Furan-3-yl-2-(4-methoxy-benzyloxy)-ethyl]-9-hydroxy-6-oxo-3-(2-oxo-propyl)-4,5,6,7,8,9-hexahydro-cycloocta[c]furan-5-carboxylic acid methyl ester

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Chemical Property of (5S,9S)-5-[(S)-2-Furan-3-yl-2-(4-methoxy-benzyloxy)-ethyl]-9-hydroxy-6-oxo-3-(2-oxo-propyl)-4,5,6,7,8,9-hexahydro-cycloocta[c]furan-5-carboxylic acid methyl ester

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Technology Process of (5S,9S)-5-[(S)-2-Furan-3-yl-2-(4-methoxy-benzyloxy)-ethyl]-9-hydroxy-6-oxo-3-(2-oxo-propyl)-4,5,6,7,8,9-hexahydro-cycloocta[c]furan-5-carboxylic acid methyl ester

There total 30 articles about (5S,9S)-5-[(S)-2-Furan-3-yl-2-(4-methoxy-benzyloxy)-ethyl]-9-hydroxy-6-oxo-3-(2-oxo-propyl)-4,5,6,7,8,9-hexahydro-cycloocta[c]furan-5-carboxylic acid methyl ester 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: 99.0%

: 304457-16-7
9-(tert-butyl-dimethyl-silanyloxy)-5-[2-furan-3-yl-2-(4-methoxy-benzyloxy)-ethyl]-6-oxo-3-(2,5,5-trimethyl-[1,3]dioxan-2-ylmethyl)-4,5,6,7,8,9-hexahydro-cycloocta[c]furan-5-carboxylic acid methyl ester

: 304457-17-8
(5S,9S)-5-[(S)-2-Furan-3-yl-2-(4-methoxy-benzyloxy)-ethyl]-9-hydroxy-6-oxo-3-(2-oxo-propyl)-4,5,6,7,8,9-hexahydro-cycloocta[c]furan-5-carboxylic acid methyl ester

Guidance literature:: With hydrogenchloride; In acetone; for 18h;
DOI:10.1021/ja002450x

Reference yield:

: 304457-09-8
2-[2-(3-(2-cyanoethyl)-4-formyl)furyl]methyl-2,5,5-trimethyl-1,3-dioxane

: 304457-17-8
(5S,9S)-5-[(S)-2-Furan-3-yl-2-(4-methoxy-benzyloxy)-ethyl]-9-hydroxy-6-oxo-3-(2-oxo-propyl)-4,5,6,7,8,9-hexahydro-cycloocta[c]furan-5-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 13 steps

1.1: tin triflate; N-ethylpiperidine / CH₂Cl₂ / 4 h / -50 - -40 °C

1.2: 80 percent / CH₂Cl₂ / 2 h / -78 °C

2.1: 95 percent / 2,6-lutidine / CH₂Cl₂ / -78 - 0 °C

3.1: H₂O / diethyl ether

3.2: 93 percent / LiBH₄ / diethyl ether / 0 - 20 °C

4.1: 81 percent / tributylphosphine; pyridine / tetrahydrofuran / 6 h / 20 °C

5.1: aq. H₂O₂ / tetrahydrofuran / 0 - 20 °C

5.2: 95 percent / diisopropylethylamine / tetrahydrofuran / 0.33 h / 45 °C

6.1: 95 percent / DIBAL / CH₂Cl₂; hexane / 2 h / -78 °C

7.1: 97 percent / tetrahydrofuran / -78 - 0 °C

8.1: 90 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / -78 - 10 °C

9.1: 81 percent / (Cy₃P)Cl₂Ru(=CHPh)(1,3-di-Mes-4,5-dihydroimidazol-2-ylidene) / CH₂Cl₂ / 34 h / Heating

10.1: LHMDS / tetrahydrofuran / 1.5 h / 0 °C

10.2: 87 percent / tetrahydrofuran; hexamethylphosphoric acid triamide / 0.5 h / -78 °C

11.1: 89 percent / H₂ / 5percent Pd/C / methanol / 0.25 h

12.1: 61 percent / Cs₂CO₃ / dimethylsulfoxide / 15 h / 50 °C

13.1: 99 percent / 1.0 M aq. HCl / acetone / 18 h

With 1-ethyl-piperidine; pyridine; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; 2,6-dimethylpyridine; hydrogenchloride; tin trifluoromethanesulfonate; oxalyl dichloride; tributylphosphine; water; hydrogen; dihydrogen peroxide; diisobutylaluminium hydride; caesium carbonate; dimethyl sulfoxide; triethylamine; lithium hexamethyldisilazane; 5percent Pd/C; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; dimethyl sulfoxide; acetone; 8.1: Swern oxidation;
DOI:10.1021/ja010313+

Reference yield:

: 345641-37-4
2-[2-(3-(2-cyanoethyl)-4-hydroxymethyl)furyl]methyl-2,5,5-trimethyl-1,3-dioxane

: 304457-17-8
(5S,9S)-5-[(S)-2-Furan-3-yl-2-(4-methoxy-benzyloxy)-ethyl]-9-hydroxy-6-oxo-3-(2-oxo-propyl)-4,5,6,7,8,9-hexahydro-cycloocta[c]furan-5-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 14 steps

1.1: 95 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

2.1: tin triflate; N-ethylpiperidine / CH₂Cl₂ / 4 h / -50 - -40 °C

2.2: 80 percent / CH₂Cl₂ / 2 h / -78 °C

3.1: 95 percent / 2,6-lutidine / CH₂Cl₂ / -78 - 0 °C

4.1: H₂O / diethyl ether

4.2: 93 percent / LiBH₄ / diethyl ether / 0 - 20 °C

5.1: 81 percent / tributylphosphine; pyridine / tetrahydrofuran / 6 h / 20 °C

6.1: aq. H₂O₂ / tetrahydrofuran / 0 - 20 °C

6.2: 95 percent / diisopropylethylamine / tetrahydrofuran / 0.33 h / 45 °C

7.1: 95 percent / DIBAL / CH₂Cl₂; hexane / 2 h / -78 °C

8.1: 97 percent / tetrahydrofuran / -78 - 0 °C

9.1: 90 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / -78 - 10 °C

10.1: 81 percent / (Cy₃P)Cl₂Ru(=CHPh)(1,3-di-Mes-4,5-dihydroimidazol-2-ylidene) / CH₂Cl₂ / 34 h / Heating

11.1: LHMDS / tetrahydrofuran / 1.5 h / 0 °C

11.2: 87 percent / tetrahydrofuran; hexamethylphosphoric acid triamide / 0.5 h / -78 °C

12.1: 89 percent / H₂ / 5percent Pd/C / methanol / 0.25 h

13.1: 61 percent / Cs₂CO₃ / dimethylsulfoxide / 15 h / 50 °C

14.1: 99 percent / 1.0 M aq. HCl / acetone / 18 h

With 1-ethyl-piperidine; pyridine; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; 2,6-dimethylpyridine; hydrogenchloride; tin trifluoromethanesulfonate; oxalyl dichloride; tributylphosphine; water; hydrogen; dihydrogen peroxide; diisobutylaluminium hydride; caesium carbonate; dimethyl sulfoxide; triethylamine; lithium hexamethyldisilazane; 5percent Pd/C; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; dimethyl sulfoxide; acetone; 1.1: Swern oxidation / 9.1: Swern oxidation;
DOI:10.1021/ja010313+