formic acid (1R,2S)-6-(2-benzyloxyethyl)-2-formyl-4,7-dimethoxy-2,5-dimethylindan-1-yl ester

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Chemical Name:formic acid (1R,2S)-6-(2-benzyloxyethyl)-2-formyl-4,7-dimethoxy-2,5-dimethylindan-1-yl ester
CAS No.:716367-73-6
Molecular Formula:C₂₄H₂₈O₆
Molecular Weight:412.483
Hs Code.:

Synonyms:formic acid (1R,2S)-6-(2-benzyloxyethyl)-2-formyl-4,7-dimethoxy-2,5-dimethylindan-1-yl ester

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Chemical Property of formic acid (1R,2S)-6-(2-benzyloxyethyl)-2-formyl-4,7-dimethoxy-2,5-dimethylindan-1-yl ester

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Technology Process of formic acid (1R,2S)-6-(2-benzyloxyethyl)-2-formyl-4,7-dimethoxy-2,5-dimethylindan-1-yl ester

There total 30 articles about formic acid (1R,2S)-6-(2-benzyloxyethyl)-2-formyl-4,7-dimethoxy-2,5-dimethylindan-1-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:

: 139976-21-9
2-bromo-6-hydroxy-4-methylbenzaldehyde

: 716367-73-6
formic acid (1R,2S)-6-(2-benzyloxyethyl)-2-formyl-4,7-dimethoxy-2,5-dimethylindan-1-yl ester

Guidance literature:: Multi-step reaction with 24 steps

1.1: 79 percent / sodium hydride / dimethylformamide / 7 h

2.1: 66 percent / decahydronaphthalene / 7 h / Heating

3.1: 83 percent / PhI(OAc)2

4.1: 70 percent / zinc; acetic acid / 7 h

5.1: 92 percent / K₂CO₃ / dimethylformamide

6.1: 97 percent / TsOH*H₂O / methanol / Heating

7.1: 95 percent / OsO₄; NaIO₄ / CCl₄; H₂O; 2-methyl-propan-2-ol / 1.5 h

8.1: 95 percent / NaBH₄ / methanol / 1.5 h / 0 °C

9.1: 92 percent / sodium hydride / tetrahydrofuran; various solvent(s) / 0 °C

10.1: 95 percent / Amberlite IR 120 / acetone; H₂O

11.1: 66 percent / Pd(PPh₃)4; CuI / toluene / 40 h / Heating

12.1: Bu₂BOSO₂CF₃; diisopropylethylamine / CH₂Cl₂ / 2 h / -78 - 0 °C

12.2: CH₂Cl₂ / 7.5 h

12.3: 87 percent / H₂O₂ / CH₂Cl₂; methanol; H₂O / 1 h / 0 °C / pH 7

13.1: 95 percent / 2,6-lutidine / CH₂Cl₂ / 1 h

14.1: 89 percent / n-BuLi / hexane; tetrahydrofuran / 6 h / 0 °C

15.1: 89 percent / iBu₂AlH / CH₂Cl₂ / -78 - 0 °C

16.1: 93 percent / n-Bu₃P / tetrahydrofuran

17.1: 22 mg / H₂O₂ / tetrahydrofuran / 5 h

18.1: 95 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 36 h

19.1: 88 percent / benzylideneruthenium(IV) dichloride based catalyst / CH₂Cl₂ / 20 h / Heating

20.1: 91 percent / 2,6-lutidine / CH₂Cl₂ / 20 h

21.1: 85 percent / Bu₃SnH; AIBN / toluene / 1.5 h / 115 °C

22.1: 91 percent / acetic acid / H₂O; tetrahydrofuran / 12 h / 50 °C

23.1: 75 percent / triethylamine; CH₃SO₂Cl / tetrahydrofuran / 3 h

24.1: OsO₄; NaIO₄ / CCl₄; H₂O; 2-methyl-propan-2-ol / 9 h

With 2,6-dimethylpyridine; sodium tetrahydroborate; sodium periodate; copper(l) iodide; osmium(VIII) oxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; 2,2'-azobis(isobutyronitrile); tributylphosphine; [bis(acetoxy)iodo]benzene; Amberlite IR 120; benzylideneruthenium(IV) dichloride based catalyst; di-n-butylboryl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; dihydrogen peroxide; tri-n-butyl-tin hydride; sodium hydride; diisobutylaluminium hydride; potassium carbonate; toluene-4-sulfonic acid; acetic acid; methanesulfonyl chloride; triethylamine; N-ethyl-N,N-diisopropylamine; zinc; In tetrahydrofuran; methanol; tetrachloromethane; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; decalin; tert-butyl alcohol; 2.1: Claisen rearrangement / 11.1: Stille coupling;
DOI:10.1021/jo040115b

Reference yield:

: 479633-78-8
3-allyl-6-bromo-2-hydroxy-4-methylbenzaldehyde

: 716367-73-6
formic acid (1R,2S)-6-(2-benzyloxyethyl)-2-formyl-4,7-dimethoxy-2,5-dimethylindan-1-yl ester

Guidance literature:: Multi-step reaction with 22 steps

1.1: 83 percent / PhI(OAc)2

2.1: 70 percent / zinc; acetic acid / 7 h

3.1: 92 percent / K₂CO₃ / dimethylformamide

4.1: 97 percent / TsOH*H₂O / methanol / Heating

5.1: 95 percent / OsO₄; NaIO₄ / CCl₄; H₂O; 2-methyl-propan-2-ol / 1.5 h

6.1: 95 percent / NaBH₄ / methanol / 1.5 h / 0 °C

7.1: 92 percent / sodium hydride / tetrahydrofuran; various solvent(s) / 0 °C

8.1: 95 percent / Amberlite IR 120 / acetone; H₂O

9.1: 66 percent / Pd(PPh₃)4; CuI / toluene / 40 h / Heating

10.1: Bu₂BOSO₂CF₃; diisopropylethylamine / CH₂Cl₂ / 2 h / -78 - 0 °C

10.2: CH₂Cl₂ / 7.5 h

10.3: 87 percent / H₂O₂ / CH₂Cl₂; methanol; H₂O / 1 h / 0 °C / pH 7

11.1: 95 percent / 2,6-lutidine / CH₂Cl₂ / 1 h

12.1: 89 percent / n-BuLi / hexane; tetrahydrofuran / 6 h / 0 °C

13.1: 89 percent / iBu₂AlH / CH₂Cl₂ / -78 - 0 °C

14.1: 93 percent / n-Bu₃P / tetrahydrofuran

15.1: 22 mg / H₂O₂ / tetrahydrofuran / 5 h

16.1: 95 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 36 h

17.1: 88 percent / benzylideneruthenium(IV) dichloride based catalyst / CH₂Cl₂ / 20 h / Heating

18.1: 91 percent / 2,6-lutidine / CH₂Cl₂ / 20 h

19.1: 85 percent / Bu₃SnH; AIBN / toluene / 1.5 h / 115 °C

20.1: 91 percent / acetic acid / H₂O; tetrahydrofuran / 12 h / 50 °C

21.1: 75 percent / triethylamine; CH₃SO₂Cl / tetrahydrofuran / 3 h

22.1: OsO₄; NaIO₄ / CCl₄; H₂O; 2-methyl-propan-2-ol / 9 h

With 2,6-dimethylpyridine; sodium tetrahydroborate; sodium periodate; copper(l) iodide; osmium(VIII) oxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; 2,2'-azobis(isobutyronitrile); tributylphosphine; [bis(acetoxy)iodo]benzene; Amberlite IR 120; benzylideneruthenium(IV) dichloride based catalyst; di-n-butylboryl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; dihydrogen peroxide; tri-n-butyl-tin hydride; sodium hydride; diisobutylaluminium hydride; potassium carbonate; toluene-4-sulfonic acid; acetic acid; methanesulfonyl chloride; triethylamine; N-ethyl-N,N-diisopropylamine; zinc; In tetrahydrofuran; methanol; tetrachloromethane; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; tert-butyl alcohol; 9.1: Stille coupling;
DOI:10.1021/jo040115b

Reference yield:

: 479633-77-7
2-allyloxy-6-bromo-4-methylbenzaldehyde

: 716367-73-6
formic acid (1R,2S)-6-(2-benzyloxyethyl)-2-formyl-4,7-dimethoxy-2,5-dimethylindan-1-yl ester

Guidance literature:: Multi-step reaction with 23 steps

1.1: 66 percent / decahydronaphthalene / 7 h / Heating

2.1: 83 percent / PhI(OAc)2

3.1: 70 percent / zinc; acetic acid / 7 h

4.1: 92 percent / K₂CO₃ / dimethylformamide

5.1: 97 percent / TsOH*H₂O / methanol / Heating

6.1: 95 percent / OsO₄; NaIO₄ / CCl₄; H₂O; 2-methyl-propan-2-ol / 1.5 h

7.1: 95 percent / NaBH₄ / methanol / 1.5 h / 0 °C

8.1: 92 percent / sodium hydride / tetrahydrofuran; various solvent(s) / 0 °C

9.1: 95 percent / Amberlite IR 120 / acetone; H₂O

10.1: 66 percent / Pd(PPh₃)4; CuI / toluene / 40 h / Heating

11.1: Bu₂BOSO₂CF₃; diisopropylethylamine / CH₂Cl₂ / 2 h / -78 - 0 °C

11.2: CH₂Cl₂ / 7.5 h

11.3: 87 percent / H₂O₂ / CH₂Cl₂; methanol; H₂O / 1 h / 0 °C / pH 7

12.1: 95 percent / 2,6-lutidine / CH₂Cl₂ / 1 h

13.1: 89 percent / n-BuLi / hexane; tetrahydrofuran / 6 h / 0 °C

14.1: 89 percent / iBu₂AlH / CH₂Cl₂ / -78 - 0 °C

15.1: 93 percent / n-Bu₃P / tetrahydrofuran

16.1: 22 mg / H₂O₂ / tetrahydrofuran / 5 h

17.1: 95 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 36 h

18.1: 88 percent / benzylideneruthenium(IV) dichloride based catalyst / CH₂Cl₂ / 20 h / Heating

19.1: 91 percent / 2,6-lutidine / CH₂Cl₂ / 20 h

20.1: 85 percent / Bu₃SnH; AIBN / toluene / 1.5 h / 115 °C

21.1: 91 percent / acetic acid / H₂O; tetrahydrofuran / 12 h / 50 °C

22.1: 75 percent / triethylamine; CH₃SO₂Cl / tetrahydrofuran / 3 h

23.1: OsO₄; NaIO₄ / CCl₄; H₂O; 2-methyl-propan-2-ol / 9 h

With 2,6-dimethylpyridine; sodium tetrahydroborate; sodium periodate; copper(l) iodide; osmium(VIII) oxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; 2,2'-azobis(isobutyronitrile); tributylphosphine; [bis(acetoxy)iodo]benzene; Amberlite IR 120; benzylideneruthenium(IV) dichloride based catalyst; di-n-butylboryl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; dihydrogen peroxide; tri-n-butyl-tin hydride; sodium hydride; diisobutylaluminium hydride; potassium carbonate; toluene-4-sulfonic acid; acetic acid; methanesulfonyl chloride; triethylamine; N-ethyl-N,N-diisopropylamine; zinc; In tetrahydrofuran; methanol; tetrachloromethane; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; decalin; tert-butyl alcohol; 1.1: Claisen rearrangement / 10.1: Stille coupling;
DOI:10.1021/jo040115b