(5R,9S)-9-Acetoxy-5-[(S)-2-furan-3-yl-2-(4-methoxy-benzyloxy)-ethyl]-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:(5R,9S)-9-Acetoxy-5-[(S)-2-furan-3-yl-2-(4-methoxy-benzyloxy)-ethyl]-6-oxo-3-(2-oxo-propyl)-4,5,6,7,8,9-hexahydro-cycloocta[c]furan-5-carboxylic acid methyl ester
CAS No.:345641-49-8
Molecular Formula:C₃₁H₃₄O₁₀
Molecular Weight:566.605
Hs Code.:

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

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

Suppliers and Price of (5R,9S)-9-Acetoxy-5-[(S)-2-furan-3-yl-2-(4-methoxy-benzyloxy)-ethyl]-6-oxo-3-(2-oxo-propyl)-4,5,6,7,8,9-hexahydro-cycloocta[c]furan-5-carboxylic acid methyl ester

Supply Marketing:

Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

Manufacturers and distributors:

Manufacture/Brand
Chemicals and raw materials
Packaging
price

Total 0 raw suppliers

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

Chemical Property:

Purity/Quality:

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:

Useful:

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

There total 31 articles about (5R,9S)-9-Acetoxy-5-[(S)-2-furan-3-yl-2-(4-methoxy-benzyloxy)-ethyl]-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:

: 304457-08-7
2-[2-(4-tert-butyldimethylsilyloxymethyl-3-(2-cyanoethyl))furyl]-methyl-2,5,5-trimethyl-1,3-dioxane

: 345641-49-8
(5R,9S)-9-Acetoxy-5-[(S)-2-furan-3-yl-2-(4-methoxy-benzyloxy)-ethyl]-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 16 steps

1.1: 98 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1 h / 0 °C

2.1: 95 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

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

3.2: 80 percent / CH₂Cl₂ / 2 h / -78 °C

4.1: 95 percent / 2,6-lutidine / CH₂Cl₂ / -78 - 0 °C

5.1: H₂O / diethyl ether

5.2: 93 percent / LiBH₄ / diethyl ether / 0 - 20 °C

6.1: 81 percent / tributylphosphine; pyridine / tetrahydrofuran / 6 h / 20 °C

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

7.2: 95 percent / diisopropylethylamine / tetrahydrofuran / 0.33 h / 45 °C

8.1: 95 percent / DIBAL / CH₂Cl₂; hexane / 2 h / -78 °C

9.1: 97 percent / tetrahydrofuran / -78 - 0 °C

10.1: 90 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / -78 - 10 °C

11.1: 81 percent / (Cy₃P)Cl₂Ru(=CHPh)(1,3-di-Mes-4,5-dihydroimidazol-2-ylidene) / CH₂Cl₂ / 34 h / Heating

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

12.2: 87 percent / tetrahydrofuran; hexamethylphosphoric acid triamide / 0.5 h / -78 °C

13.1: 89 percent / H₂ / 5percent Pd/C / methanol / 0.25 h

14.1: 15 percent / Cs₂CO₃ / dimethylsulfoxide / 15 h / 50 °C

15.1: 1.0 M aq. HCl / acetone / 18 h

16.1: DMAP / CH₂Cl₂ / 0.75 h / 20 °C

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; dmap; tin trifluoromethanesulfonate; oxalyl dichloride; tributylphosphine; tetrabutyl ammonium fluoride; 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; 2.1: Swern oxidation / 10.1: Swern oxidation;
DOI:10.1021/ja010313+

Reference yield:

: 304457-04-3
4-phenyl-2-(2,5,5-trimethyl-[1,3]dioxan-2-ylmethyl)-oxazole

: 345641-49-8
(5R,9S)-9-Acetoxy-5-[(S)-2-furan-3-yl-2-(4-methoxy-benzyloxy)-ethyl]-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 20 steps

1.1: 26 percent / 2,6-lutidine; hydroquinone / 1,2,3,4-tetrahydro-naphthalene / 39 h / 205 - 208 °C

2.1: 91 percent / NaBH₄ / ethanol / 6 h / 20 °C

3.1: 72 percent / methanesulfonyl bromide; triethylamine / CH₂Cl₂ / 46 h / 0 °C

4.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C

4.2: 64 percent / tetrahydrofuran; hexane / 0.25 h / 0 °C

5.1: 98 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1 h / 0 °C

6.1: 95 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

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

7.2: 80 percent / CH₂Cl₂ / 2 h / -78 °C

8.1: 95 percent / 2,6-lutidine / CH₂Cl₂ / -78 - 0 °C

9.1: H₂O / diethyl ether

9.2: 93 percent / LiBH₄ / diethyl ether / 0 - 20 °C

10.1: 81 percent / tributylphosphine; pyridine / tetrahydrofuran / 6 h / 20 °C

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

11.2: 95 percent / diisopropylethylamine / tetrahydrofuran / 0.33 h / 45 °C

12.1: 95 percent / DIBAL / CH₂Cl₂; hexane / 2 h / -78 °C

13.1: 97 percent / tetrahydrofuran / -78 - 0 °C

14.1: 90 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / -78 - 10 °C

15.1: 81 percent / (Cy₃P)Cl₂Ru(=CHPh)(1,3-di-Mes-4,5-dihydroimidazol-2-ylidene) / CH₂Cl₂ / 34 h / Heating

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

16.2: 87 percent / tetrahydrofuran; hexamethylphosphoric acid triamide / 0.5 h / -78 °C

17.1: 89 percent / H₂ / 5percent Pd/C / methanol / 0.25 h

18.1: 15 percent / Cs₂CO₃ / dimethylsulfoxide / 15 h / 50 °C

19.1: 1.0 M aq. HCl / acetone / 18 h

20.1: DMAP / CH₂Cl₂ / 0.75 h / 20 °C

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; dmap; sodium tetrahydroborate; n-butyllithium; tin trifluoromethanesulfonate; oxalyl dichloride; tributylphosphine; methanesulfonyl bromide; tetrabutyl ammonium fluoride; water; hydrogen; dihydrogen peroxide; diisobutylaluminium hydride; caesium carbonate; dimethyl sulfoxide; triethylamine; hydroquinone; lithium hexamethyldisilazane; 5percent Pd/C; In tetrahydrofuran; methanol; tetralin; diethyl ether; ethanol; hexane; dichloromethane; dimethyl sulfoxide; acetone; 6.1: Swern oxidation / 14.1: Swern oxidation;
DOI:10.1021/ja010313+

Reference yield:

: 304457-19-0
3-[4-[1-(tert-butyl-dimethyl-silanyloxy)-allyl]-2-(2,5,5-trimethyl-[1,3]dioxan-2-ylmethyl)-furan-3-yl]-propionaldehyde

: 345641-49-8
(5R,9S)-9-Acetoxy-5-[(S)-2-furan-3-yl-2-(4-methoxy-benzyloxy)-ethyl]-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 8 steps

1.1: 97 percent / tetrahydrofuran / -78 - 0 °C

2.1: 90 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / -78 - 10 °C

3.1: 81 percent / (Cy₃P)Cl₂Ru(=CHPh)(1,3-di-Mes-4,5-dihydroimidazol-2-ylidene) / CH₂Cl₂ / 34 h / Heating

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

4.2: 87 percent / tetrahydrofuran; hexamethylphosphoric acid triamide / 0.5 h / -78 °C

5.1: 89 percent / H₂ / 5percent Pd/C / methanol / 0.25 h

6.1: 15 percent / Cs₂CO₃ / dimethylsulfoxide / 15 h / 50 °C

7.1: 1.0 M aq. HCl / acetone / 18 h

8.1: DMAP / CH₂Cl₂ / 0.75 h / 20 °C

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; hydrogenchloride; dmap; oxalyl dichloride; hydrogen; caesium carbonate; dimethyl sulfoxide; triethylamine; lithium hexamethyldisilazane; 5percent Pd/C; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; acetone; 2.1: Swern oxidation;
DOI:10.1021/ja010313+