(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

Base Information

• Chemical Name: (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
• CAS No.: 807617-07-8
• Molecular Formula: C₄₅H₇₂O₇Si₃
• Molecular Weight: 809.319

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

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Technology Process of (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

There total 27 articles about (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 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) → (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 (807617-07-8)

Guidance literature:

Multi-step reaction with 27 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

25.1: LiAlH₄ / diethyl ether / 0.5 h / 0 °C

25.2: 654 mg / aq. NaOH / diethyl ether / 0.5 h / 20 °C

26.1: 128.2 mg / imidazole / dimethylformamide / 2 h / 20 °C

27.1: 107.3 mg / MS₄A; NMO; TPAP / CH₂Cl₂ / 1 h / 20 °C

With 4-methyl-morpholine; pyridine; 1H-imidazole; titanium(IV) isopropylate; lithium aluminium tetrahydride; 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; diethyl ether; 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) → (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 (807617-07-8)

Guidance literature:

Multi-step reaction with 23 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

21.1: LiAlH₄ / diethyl ether / 0.5 h / 0 °C

21.2: 654 mg / aq. NaOH / diethyl ether / 0.5 h / 20 °C

22.1: 128.2 mg / imidazole / dimethylformamide / 2 h / 20 °C

23.1: 107.3 mg / MS₄A; NMO; TPAP / CH₂Cl₂ / 1 h / 20 °C

With pyridine; 1H-imidazole; titanium(IV) isopropylate; lithium aluminium tetrahydride; 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; diethyl ether; 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 → (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 (807617-07-8)

Guidance literature:

Multi-step reaction with 22 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

20.1: LiAlH₄ / diethyl ether / 0.5 h / 0 °C

20.2: 654 mg / aq. NaOH / diethyl ether / 0.5 h / 20 °C

21.1: 128.2 mg / imidazole / dimethylformamide / 2 h / 20 °C

22.1: 107.3 mg / MS₄A; NMO; TPAP / CH₂Cl₂ / 1 h / 20 °C

With pyridine; 1H-imidazole; titanium(IV) isopropylate; lithium aluminium tetrahydride; 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; diethyl ether; 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:

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

tert-butyldimethylsilyl chloride

((4aR,6S,7R,8aS)-7-Hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl)-acetic acid ethyl ester

(4S,5R)-4-[1,3]Dithian-2-ylmethyl-2-phenyl-[1,3]dioxan-5-ol

Downstream raw materials:

(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

{(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

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