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

Base Information

Chemical Name: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
CAS No.:304457-21-4
Molecular Formula:C₄₀H₅₆O₁₀Si
Molecular Weight:724.964
Hs Code.:

9-(<i>tert</i>-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[<i>c</i>]furan-5-carboxylic acid methyl ester

Synonyms: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

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Chemical Property of 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

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Technology Process of 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

There total 31 articles about 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 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%

: 304457-15-6
1-(1R)-1-(3-furyl)-2-(iodoethyl)-p-methoxybenzyl ether

: 304457-14-5
9-(tert-butyl-dimethyl-silanyloxy)-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

: 304457-16-7
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

: 304457-21-4
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

Guidance literature:: With caesium carbonate; In dimethyl sulfoxide; at 50 ℃; for 15h;
DOI:10.1021/ja002450x

Reference yield:

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

: 304457-21-4
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

Guidance literature:: Multi-step reaction with 18 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

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; 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; 6.1: Swern oxidation / 14.1: Swern oxidation;
DOI:10.1021/ja010313+

Reference yield:

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

: 304457-21-4
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

Guidance literature:: Multi-step reaction with 12 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: 15 percent / Cs₂CO₃ / dimethylsulfoxide / 15 h / 50 °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; 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; 8.1: Swern oxidation;
DOI:10.1021/ja010313+