2,2-Dimethyl-propionic acid (2R,3S,4aR,5S,7R,8aR,9aS,10aR)-5-(tert-butyl-dimethyl-silanyloxy)-7-[2-(tert-butyl-diphenyl-silanyloxymethyl)-allyl]-2-(2,2-dimethyl-propionyloxymethyl)-10a-methyl-decahydro-1,8,10-trioxa-anthracen-3-yl ester

Base Information

• Chemical Name: 2,2-Dimethyl-propionic acid (2R,3S,4aR,5S,7R,8aR,9aS,10aR)-5-(tert-butyl-dimethyl-silanyloxy)-7-[2-(tert-butyl-diphenyl-silanyloxymethyl)-allyl]-2-(2,2-dimethyl-propionyloxymethyl)-10a-methyl-decahydro-1,8,10-trioxa-anthracen-3-yl ester
• CAS No.: 807617-38-5
• Molecular Formula: C₄₉H₇₆O₉Si₂
• Molecular Weight: 865.308
• Mol file: 807617-38-5.mol

Synonyms:2,2-Dimethyl-propionic acid (2R,3S,4aR,5S,7R,8aR,9aS,10aR)-5-(tert-butyl-dimethyl-silanyloxy)-7-[2-(tert-butyl-diphenyl-silanyloxymethyl)-allyl]-2-(2,2-dimethyl-propionyloxymethyl)-10a-methyl-decahydro-1,8,10-trioxa-anthracen-3-yl ester

Chemical Property of 2,2-Dimethyl-propionic acid (2R,3S,4aR,5S,7R,8aR,9aS,10aR)-5-(tert-butyl-dimethyl-silanyloxy)-7-[2-(tert-butyl-diphenyl-silanyloxymethyl)-allyl]-2-(2,2-dimethyl-propionyloxymethyl)-10a-methyl-decahydro-1,8,10-trioxa-anthracen-3-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,2-Dimethyl-propionic acid (2R,3S,4aR,5S,7R,8aR,9aS,10aR)-5-(tert-butyl-dimethyl-silanyloxy)-7-[2-(tert-butyl-diphenyl-silanyloxymethyl)-allyl]-2-(2,2-dimethyl-propionyloxymethyl)-10a-methyl-decahydro-1,8,10-trioxa-anthracen-3-yl ester

There total 25 articles about 2,2-Dimethyl-propionic acid (2R,3S,4aR,5S,7R,8aR,9aS,10aR)-5-(tert-butyl-dimethyl-silanyloxy)-7-[2-(tert-butyl-diphenyl-silanyloxymethyl)-allyl]-2-(2,2-dimethyl-propionyloxymethyl)-10a-methyl-decahydro-1,8,10-trioxa-anthracen-3-yl 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:

2-deoxy-D-erythro-pentose cyclic 1,3-propanediyl mercaptal (50907-65-8) → 2,2-Dimethyl-propionic acid (2R,3S,4aR,5S,7R,8aR,9aS,10aR)-5-(tert-butyl-dimethyl-silanyloxy)-7-[2-(tert-butyl-diphenyl-silanyloxymethyl)-allyl]-2-(2,2-dimethyl-propionyloxymethyl)-10a-methyl-decahydro-1,8,10-trioxa-anthracen-3-yl ester (807617-38-5)

Guidance literature:

Multi-step reaction with 24 steps

1.1: 170 mg / CSA / ethyl acetate / 16 h / 20 °C

2.1: 173 mg / N-methylmorpholine / CH₂Cl₂ / 4 h / 20 °C

3.1: 98 percent / NaHCO₃; MeI / acetonitrile / 22 h / 20 °C

4.1: 95 percent / SmI₂ / tetrahydrofuran; methanol / 0.17 h / 0 °C

5.1: DIBAL-H / CH₂Cl₂; hexane / 1 h / -78 °C

6.1: 3.19 g / toluene / 0.5 h / 100 °C

7.1: 4.47 g / imidazole / dimethylformamide / 15 h / 20 °C

8.1: 3.25 g / DIBAL-Hi₁₉₈ / toluene; hexane / 0.5 h / -78 °C

9.1: MS₄A; diethyl (-)-tartarate; Ti(O-iPr)4 / CH₂Cl₂ / 0.5 h / -20 °C

9.2: 98 percent / TBHP / CH₂Cl₂ / 18 h / -20 °C

10.1: MS₄A; NMO; TPAP / CH₂Cl₂ / 0.33 h / 20 °C

11.1: 272.7 mg / NaHMDS / tetrahydrofuran / 0.17 h / 0 °C

12.1: TBAF / tetrahydrofuran / 1 h / 20 °C

13.1: 176.6 mg / PPTS / CH₂Cl₂ / 2 h / 20 °C

14.1: 97 percent / pyridine / CH₂Cl₂ / 0.25 h / 0 °C

15.1: O₃ / CH₂Cl₂ / -78 °C

15.2: Me₂S / CH₂Cl₂ / 0.17 h / 20 °C

16.1: 18.3 mg / SmI₂ / tetrahydrofuran / 0.17 h / 0 °C

17.1: 71 percent / pyridine / CH₂Cl₂ / 1.5 h / 20 °C

18.1: DIBAL-H / CH₂Cl₂; hexane / 0.25 h / -78 °C

18.2: aq. NaOH / CH₂Cl₂; hexane; diethyl ether / 0.5 h / 20 °C

19.1: 470 mg / pyridine / 2 h / 20 °C

20.1: H₂ / Pd(OH)2/C / ethyl acetate / 2 h / 20 °C

21.1: 865 mg / pyridine / 15 h / 20 °C

22.1: TMSOTf / acetonitrile / 0.17 h / -20 °C

22.2: 712.6 mg / pyridine; TBSOTf / CH₂Cl₂ / 1 h / 20 °C

23.1: 678 mg / K₂CO₃ / methanol / 16 h / -5 °C

24.1: 1.23 g / imidazole / dimethylformamide / 1 h / 20 °C

With 4-methyl-morpholine; pyridine; 1H-imidazole; titanium(IV) isopropylate; N-methyl-2-indolinone; samarium diiodide; tetrapropylammonium perruthennate; diethyl (2S,3S)-tartrate; trimethylsilyl trifluoromethanesulfonate; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; hydrogen; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; sodium hydrogencarbonate; potassium carbonate; ozone; methyl iodide; palladium dihydroxide; In tetrahydrofuran; methanol; hexane; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; toluene; acetonitrile; 2.1: hetero-Michael reaction / 6.1: Wittig reaction / 9.1: Sharpless asymmetric epoxidation / 16.1: intramolecular Reformatsky-type reaction;

DOI:10.1021/ja0449269

Reference yield:

((4aR,6S,7R,8aS)-7-Hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl)-acetic acid ethyl ester (476687-71-5) → 2,2-Dimethyl-propionic acid (2R,3S,4aR,5S,7R,8aR,9aS,10aR)-5-(tert-butyl-dimethyl-silanyloxy)-7-[2-(tert-butyl-diphenyl-silanyloxymethyl)-allyl]-2-(2,2-dimethyl-propionyloxymethyl)-10a-methyl-decahydro-1,8,10-trioxa-anthracen-3-yl ester (807617-38-5)

Guidance literature:

Multi-step reaction with 20 steps

1.1: DIBAL-H / CH₂Cl₂; hexane / 1 h / -78 °C

2.1: 3.19 g / toluene / 0.5 h / 100 °C

3.1: 4.47 g / imidazole / dimethylformamide / 15 h / 20 °C

4.1: 3.25 g / DIBAL-Hi₁₉₈ / toluene; hexane / 0.5 h / -78 °C

5.1: MS₄A; diethyl (-)-tartarate; Ti(O-iPr)4 / CH₂Cl₂ / 0.5 h / -20 °C

5.2: 98 percent / TBHP / CH₂Cl₂ / 18 h / -20 °C

6.1: MS₄A; NMO; TPAP / CH₂Cl₂ / 0.33 h / 20 °C

7.1: 272.7 mg / NaHMDS / tetrahydrofuran / 0.17 h / 0 °C

8.1: TBAF / tetrahydrofuran / 1 h / 20 °C

9.1: 176.6 mg / PPTS / CH₂Cl₂ / 2 h / 20 °C

10.1: 97 percent / pyridine / CH₂Cl₂ / 0.25 h / 0 °C

11.1: O₃ / CH₂Cl₂ / -78 °C

11.2: Me₂S / CH₂Cl₂ / 0.17 h / 20 °C

12.1: 18.3 mg / SmI₂ / tetrahydrofuran / 0.17 h / 0 °C

13.1: 71 percent / pyridine / CH₂Cl₂ / 1.5 h / 20 °C

14.1: DIBAL-H / CH₂Cl₂; hexane / 0.25 h / -78 °C

14.2: aq. NaOH / CH₂Cl₂; hexane; diethyl ether / 0.5 h / 20 °C

15.1: 470 mg / pyridine / 2 h / 20 °C

16.1: H₂ / Pd(OH)2/C / ethyl acetate / 2 h / 20 °C

17.1: 865 mg / pyridine / 15 h / 20 °C

18.1: TMSOTf / acetonitrile / 0.17 h / -20 °C

18.2: 712.6 mg / pyridine; TBSOTf / CH₂Cl₂ / 1 h / 20 °C

19.1: 678 mg / K₂CO₃ / methanol / 16 h / -5 °C

20.1: 1.23 g / imidazole / dimethylformamide / 1 h / 20 °C

With pyridine; 1H-imidazole; titanium(IV) isopropylate; N-methyl-2-indolinone; samarium diiodide; tetrapropylammonium perruthennate; diethyl (2S,3S)-tartrate; trimethylsilyl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; hydrogen; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; potassium carbonate; ozone; palladium dihydroxide; In tetrahydrofuran; methanol; hexane; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; toluene; acetonitrile; 2.1: Wittig reaction / 5.1: Sharpless asymmetric epoxidation / 12.1: intramolecular Reformatsky-type reaction;

DOI:10.1021/ja0449269

Reference yield:

((4aR,6S,7R,8aS)-7-Hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl)-acetaldehyde → 2,2-Dimethyl-propionic acid (2R,3S,4aR,5S,7R,8aR,9aS,10aR)-5-(tert-butyl-dimethyl-silanyloxy)-7-[2-(tert-butyl-diphenyl-silanyloxymethyl)-allyl]-2-(2,2-dimethyl-propionyloxymethyl)-10a-methyl-decahydro-1,8,10-trioxa-anthracen-3-yl ester (807617-38-5)

Guidance literature:

Multi-step reaction with 19 steps

1.1: 3.19 g / toluene / 0.5 h / 100 °C

2.1: 4.47 g / imidazole / dimethylformamide / 15 h / 20 °C

3.1: 3.25 g / DIBAL-Hi₁₉₈ / toluene; hexane / 0.5 h / -78 °C

4.1: MS₄A; diethyl (-)-tartarate; Ti(O-iPr)4 / CH₂Cl₂ / 0.5 h / -20 °C

4.2: 98 percent / TBHP / CH₂Cl₂ / 18 h / -20 °C

5.1: MS₄A; NMO; TPAP / CH₂Cl₂ / 0.33 h / 20 °C

6.1: 272.7 mg / NaHMDS / tetrahydrofuran / 0.17 h / 0 °C

7.1: TBAF / tetrahydrofuran / 1 h / 20 °C

8.1: 176.6 mg / PPTS / CH₂Cl₂ / 2 h / 20 °C

9.1: 97 percent / pyridine / CH₂Cl₂ / 0.25 h / 0 °C

10.1: O₃ / CH₂Cl₂ / -78 °C

10.2: Me₂S / CH₂Cl₂ / 0.17 h / 20 °C

11.1: 18.3 mg / SmI₂ / tetrahydrofuran / 0.17 h / 0 °C

12.1: 71 percent / pyridine / CH₂Cl₂ / 1.5 h / 20 °C

13.1: DIBAL-H / CH₂Cl₂; hexane / 0.25 h / -78 °C

13.2: aq. NaOH / CH₂Cl₂; hexane; diethyl ether / 0.5 h / 20 °C

14.1: 470 mg / pyridine / 2 h / 20 °C

15.1: H₂ / Pd(OH)2/C / ethyl acetate / 2 h / 20 °C

16.1: 865 mg / pyridine / 15 h / 20 °C

17.1: TMSOTf / acetonitrile / 0.17 h / -20 °C

17.2: 712.6 mg / pyridine; TBSOTf / CH₂Cl₂ / 1 h / 20 °C

18.1: 678 mg / K₂CO₃ / methanol / 16 h / -5 °C

19.1: 1.23 g / imidazole / dimethylformamide / 1 h / 20 °C

With pyridine; 1H-imidazole; titanium(IV) isopropylate; N-methyl-2-indolinone; samarium diiodide; tetrapropylammonium perruthennate; diethyl (2S,3S)-tartrate; trimethylsilyl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; hydrogen; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; potassium carbonate; ozone; palladium dihydroxide; In tetrahydrofuran; methanol; hexane; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; toluene; acetonitrile; 1.1: Wittig reaction / 4.1: Sharpless asymmetric epoxidation / 11.1: intramolecular Reformatsky-type reaction;

DOI:10.1021/ja0449269

upstream raw materials:

tert-butylchlorodiphenylsilane

2,2-Dimethyl-propionic acid (2R,3S,4aR,5S,7R,8aR,9aS,10aR)-5-(tert-butyl-dimethyl-silanyloxy)-2-(2,2-dimethyl-propionyloxymethyl)-7-(2-hydroxymethyl-allyl)-10a-methyl-decahydro-1,8,10-trioxa-anthracen-3-yl ester

pivaloyl chloride

2-deoxy-D-erythro-pentose cyclic 1,3-propanediyl mercaptal

Downstream raw materials:

(2R,3S,4aR,5S,7R,8aR,9aS,10aR)-5-(tert-Butyl-dimethyl-silanyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-7-[2-(tert-butyl-diphenyl-silanyloxymethyl)-allyl]-10a-methyl-decahydro-1,8,10-trioxa-anthracen-3-ol

(2R,4aR,5S,7R,8aR,9aS,10aR)-5-(tert-Butyl-dimethyl-silanyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-7-[2-(tert-butyl-diphenyl-silanyloxymethyl)-allyl]-10a-methyl-octahydro-1,8,10-trioxa-anthracen-3-one

{(2R,4aR,5S,7R,8aR,9aS,10aR)-5-(tert-Butyl-dimethyl-silanyloxy)-7-[2-(tert-butyl-diphenyl-silanyloxymethyl)-allyl]-3,3-bis-ethylsulfanyl-10a-methyl-decahydro-1,8,10-trioxa-anthracen-2-yl}-methanol

(2R,4aR,5S,7R,8aR,9aS,10aR)-5-(tert-Butyl-dimethyl-silanyloxy)-7-[2-(tert-butyl-diphenyl-silanyloxymethyl)-allyl]-3,3-bis-ethylsulfanyl-10a-methyl-decahydro-1,8,10-trioxa-anthracene-2-carbaldehyde