2,2-Dimethyl-propionic acid (1R,3R,3aS,6S,6aR)-6-(tert-butyl-diphenyl-silanyloxymethyl)-3-isopropyl-3-methoxy-3a-methyl-4-oxo-tetrahydro-furo[3,4-c]furan-1-ylmethyl ester

Base Information

Chemical Name:2,2-Dimethyl-propionic acid (1R,3R,3aS,6S,6aR)-6-(tert-butyl-diphenyl-silanyloxymethyl)-3-isopropyl-3-methoxy-3a-methyl-4-oxo-tetrahydro-furo[3,4-c]furan-1-ylmethyl ester
CAS No.:171924-81-5
Molecular Formula:C₃₄H₄₈O₇Si
Molecular Weight:596.836
Hs Code.:

2,2-Dimethyl-propionic acid (1R,3R,3aS,6S,6aR)-6-(tert-butyl-diphenyl-silanyloxymethyl)-3-isopropyl-3-methoxy-3a-methyl-4-oxo-tetrahydro-furo[3,4-c]furan-1-ylmethyl ester

Synonyms:2,2-Dimethyl-propionic acid (1R,3R,3aS,6S,6aR)-6-(tert-butyl-diphenyl-silanyloxymethyl)-3-isopropyl-3-methoxy-3a-methyl-4-oxo-tetrahydro-furo[3,4-c]furan-1-ylmethyl ester

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Chemical Property of 2,2-Dimethyl-propionic acid (1R,3R,3aS,6S,6aR)-6-(tert-butyl-diphenyl-silanyloxymethyl)-3-isopropyl-3-methoxy-3a-methyl-4-oxo-tetrahydro-furo[3,4-c]furan-1-ylmethyl ester

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Technology Process of 2,2-Dimethyl-propionic acid (1R,3R,3aS,6S,6aR)-6-(tert-butyl-diphenyl-silanyloxymethyl)-3-isopropyl-3-methoxy-3a-methyl-4-oxo-tetrahydro-furo[3,4-c]furan-1-ylmethyl ester

There total 33 articles about 2,2-Dimethyl-propionic acid (1R,3R,3aS,6S,6aR)-6-(tert-butyl-diphenyl-silanyloxymethyl)-3-isopropyl-3-methoxy-3a-methyl-4-oxo-tetrahydro-furo[3,4-c]furan-1-ylmethyl 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: 84.0%

: 58479-61-1
tert-butylchlorodiphenylsilane

: 171924-79-1
2,2-Dimethyl-propionic acid (1R,3R,3aS,6S,6aR)-6-hydroxymethyl-3-isopropyl-3-methoxy-3a-methyl-4-oxo-tetrahydro-furo[3,4-c]furan-1-ylmethyl ester

: 171924-81-5
2,2-Dimethyl-propionic acid (1R,3R,3aS,6S,6aR)-6-(tert-butyl-diphenyl-silanyloxymethyl)-3-isopropyl-3-methoxy-3a-methyl-4-oxo-tetrahydro-furo[3,4-c]furan-1-ylmethyl ester

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃; for 4h;
DOI:10.1021/ol0700862

Reference yield:

: 935252-96-3
3-allyl-butane-1,2,4-triol

: 171924-81-5
2,2-Dimethyl-propionic acid (1R,3R,3aS,6S,6aR)-6-(tert-butyl-diphenyl-silanyloxymethyl)-3-isopropyl-3-methoxy-3a-methyl-4-oxo-tetrahydro-furo[3,4-c]furan-1-ylmethyl ester

Guidance literature:: Multi-step reaction with 23 steps

1.1: 75 percent / p-TsOH / ethyl acetate / 12 h / 20 °C

2.1: 97 percent / pyridine / 0 - 20 °C

3.1: ozone / methanol; CH₂Cl₂ / -78 °C

4.1: 10.3 g / NaBH₄ / methanol; CH₂Cl₂ / -78 - -20 °C

5.1: 91 percent / imidazole / dimethylformamide / 4 h / 20 °C

6.1: 95 percent / K₂CO₃ / methanol / 72 h / 20 °C

7.1: 95 percent / [bis(acetoxy)iodo]benzene; TEMPO / CH₂Cl₂ / 1.5 h / 20 °C

8.1: 94 percent / CH₂Cl₂ / 12 h / 20 °C

9.1: 86 percent / i-Bu₂AlH / toluene; CH₂Cl₂ / 2 h / -78 °C

10.1: 80 percent / L-(+)-diisopropyl tatrtrate; Ti(OPr-i)4; t-BuO₂H / 4 Amgstroem molecular sieves / CH₂Cl₂ / 12 h / -20 °C

11.1: 97 percent / I₂; Ph₃P; imidazole / tetrahydrofuran; acetonitrile / 0.5 h / 20 °C

12.1: 91 percent / Zn / methanol / 4 h / Heating

13.1: 91 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 0 - 20 °C

14.1: 94 percent / [bis(acetoxy)iodo]benzene; TEMPO / CH₂Cl₂ / 5 h / 20 °C

15.1: 0.205 g / 1,3-propanedithiol; boron trifluoride etherate / CH₂Cl₂ / 0.03 h / -40 °C

16.1: 79 percent / pyridine / 13 h / 0 - 20 °C

17.1: 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C

18.1: LiN(SiMe₃)2 / tetrahydrofuran / 0.5 h / -78 °C

18.2: 67 percent / tetrahydrofuran / 1.5 h / -78 °C

19.1: NaH / dimethylformamide / 0.5 h / 0 °C

19.2: 89 percent / dimethylformamide / 2 h / 0 °C

20.1: 74 percent / pyridine p-toluenesulfonate / methanol / 48 h / Heating

21.1: O₃ / methanol; CH₂Cl₂ / -78 °C

22.1: 16 mg / NaBH₄ / methanol; CH₂Cl₂ / 1 h / 0 °C

23.1: 84 percent / imidazole / dimethylformamide / 4 h / 20 °C

With pyridine; 1H-imidazole; 2,6-dimethylpyridine; 1.3-propanedithiol; titanium(IV) isopropylate; tert.-butylhydroperoxide; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium tetrahydroborate; L-(+)-diisopropyl tartrate; [bis(acetoxy)iodo]benzene; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; iodine; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; potassium carbonate; toluene-4-sulfonic acid; ozone; triphenylphosphine; lithium hexamethyldisilazane; zinc; 4 A molecular sieve; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; toluene; acetonitrile; 10.1: Sharpless asymmetric epoxidation / 20.1: Fisher glycosidation;
DOI:10.1021/ol0700862

Reference yield:

: 935252-97-4
2-(1,4-dioxa-spiro[4.5]dec-2-yl)-pent-4-en-1-ol

: 171924-81-5
2,2-Dimethyl-propionic acid (1R,3R,3aS,6S,6aR)-6-(tert-butyl-diphenyl-silanyloxymethyl)-3-isopropyl-3-methoxy-3a-methyl-4-oxo-tetrahydro-furo[3,4-c]furan-1-ylmethyl ester

Guidance literature:: Multi-step reaction with 22 steps

1.1: 97 percent / pyridine / 0 - 20 °C

2.1: ozone / methanol; CH₂Cl₂ / -78 °C

3.1: 10.3 g / NaBH₄ / methanol; CH₂Cl₂ / -78 - -20 °C

4.1: 91 percent / imidazole / dimethylformamide / 4 h / 20 °C

5.1: 95 percent / K₂CO₃ / methanol / 72 h / 20 °C

6.1: 95 percent / [bis(acetoxy)iodo]benzene; TEMPO / CH₂Cl₂ / 1.5 h / 20 °C

7.1: 94 percent / CH₂Cl₂ / 12 h / 20 °C

8.1: 86 percent / i-Bu₂AlH / toluene; CH₂Cl₂ / 2 h / -78 °C

9.1: 80 percent / L-(+)-diisopropyl tatrtrate; Ti(OPr-i)4; t-BuO₂H / 4 Amgstroem molecular sieves / CH₂Cl₂ / 12 h / -20 °C

10.1: 97 percent / I₂; Ph₃P; imidazole / tetrahydrofuran; acetonitrile / 0.5 h / 20 °C

11.1: 91 percent / Zn / methanol / 4 h / Heating

12.1: 91 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 0 - 20 °C

13.1: 94 percent / [bis(acetoxy)iodo]benzene; TEMPO / CH₂Cl₂ / 5 h / 20 °C

14.1: 0.205 g / 1,3-propanedithiol; boron trifluoride etherate / CH₂Cl₂ / 0.03 h / -40 °C

15.1: 79 percent / pyridine / 13 h / 0 - 20 °C

16.1: 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C

17.1: LiN(SiMe₃)2 / tetrahydrofuran / 0.5 h / -78 °C

17.2: 67 percent / tetrahydrofuran / 1.5 h / -78 °C

18.1: NaH / dimethylformamide / 0.5 h / 0 °C

18.2: 89 percent / dimethylformamide / 2 h / 0 °C

19.1: 74 percent / pyridine p-toluenesulfonate / methanol / 48 h / Heating

20.1: O₃ / methanol; CH₂Cl₂ / -78 °C

21.1: 16 mg / NaBH₄ / methanol; CH₂Cl₂ / 1 h / 0 °C

22.1: 84 percent / imidazole / dimethylformamide / 4 h / 20 °C

With pyridine; 1H-imidazole; 2,6-dimethylpyridine; 1.3-propanedithiol; titanium(IV) isopropylate; tert.-butylhydroperoxide; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium tetrahydroborate; L-(+)-diisopropyl tartrate; [bis(acetoxy)iodo]benzene; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; iodine; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; potassium carbonate; ozone; triphenylphosphine; lithium hexamethyldisilazane; zinc; 4 A molecular sieve; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile; 9.1: Sharpless asymmetric epoxidation / 19.1: Fisher glycosidation;
DOI:10.1021/ol0700862