(3R,4S,6R,6aS,7aS,9aS,10S,11S,12R,12aS,12bS,12cR)-10,12-Dihydroxy-4,6,8,11-tetramethyl-4,6,6a,7,7a,9a,10,11,12,12a,12b,12c-dodecahydro-1H,3H-3,6-etheno-as-indaceno[1,2-d]pyrano[4,3-b]pyran-1-one

Base Information

Chemical Name:(3R,4S,6R,6aS,7aS,9aS,10S,11S,12R,12aS,12bS,12cR)-10,12-Dihydroxy-4,6,8,11-tetramethyl-4,6,6a,7,7a,9a,10,11,12,12a,12b,12c-dodecahydro-1H,3H-3,6-etheno-as-indaceno[1,2-d]pyrano[4,3-b]pyran-1-one
CAS No.:233256-51-4
Molecular Formula:C₂₄H₃₂O₅
Molecular Weight:400.515
Hs Code.:

(3R,4S,6R,6aS,7aS,9aS,10S,11S,12R,12aS,12bS,12cR)-10,12-Dihydroxy-4,6,8,11-tetramethyl-4,6,6a,7,7a,9a,10,11,12,12a,12b,12c-dodecahydro-1H,3H-3,6-etheno-as-indaceno[1,2-d]pyrano[4,3-b]pyran-1-one

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Chemical Property of (3R,4S,6R,6aS,7aS,9aS,10S,11S,12R,12aS,12bS,12cR)-10,12-Dihydroxy-4,6,8,11-tetramethyl-4,6,6a,7,7a,9a,10,11,12,12a,12b,12c-dodecahydro-1H,3H-3,6-etheno-as-indaceno[1,2-d]pyrano[4,3-b]pyran-1-one

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Technology Process of (3R,4S,6R,6aS,7aS,9aS,10S,11S,12R,12aS,12bS,12cR)-10,12-Dihydroxy-4,6,8,11-tetramethyl-4,6,6a,7,7a,9a,10,11,12,12a,12b,12c-dodecahydro-1H,3H-3,6-etheno-as-indaceno[1,2-d]pyrano[4,3-b]pyran-1-one

There total 13 articles about (3R,4S,6R,6aS,7aS,9aS,10S,11S,12R,12aS,12bS,12cR)-10,12-Dihydroxy-4,6,8,11-tetramethyl-4,6,6a,7,7a,9a,10,11,12,12a,12b,12c-dodecahydro-1H,3H-3,6-etheno-as-indaceno[1,2-d]pyrano[4,3-b]pyran-1-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:

: 431900-87-7
Acetic acid (E)-(6R,7S)-7-(methoxy-methyl-carbamoyl)-3-methyl-6-trimethylsilanyloxy-oct-2-enyl ester

: 233256-51-4
(+)-FR182877

Guidance literature:: Multi-step reaction with 12 steps

1: 85 percent / Pd₂dba3; NMP; i-Pr₂NEt / LiCl / 1.33 h / 40 °C

2: 81 percent / LDA / diethyl ether / -78 - 20 °C

3: 86 percent / TBAF / tetrahydrofuran / -40 - 0 °C

4: 93 percent / pyridine / CH₂Cl₂

5: 95 percent / imidazole / CH₂Cl₂

6: 80 percent / Pd₂dba3 / tetrahydrofuran / 12 h / 40 °C

7: 91 percent / KHMDS / tetrahydrofuran / -10 °C

8: mCPBA / CH₂Cl₂ / -40 °C

9: CHCl₃ / 4 h / 40 °C

10: PPTS / methanol

11: TFA / CH₂Cl₂ / 0 - 20 °C

12: EDC; DMAP / CH₂Cl₂

With pyridine; 1H-imidazole; 1-methyl-pyrrolidin-2-one; dmap; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; potassium hexamethylsilazane; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; lithium diisopropyl amide; lithium chloride; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; chloroform; 1: Stille coupling / 9: double transannular Diels-Alder reaction;
DOI:10.1021/ja025885o

Reference yield:

: 393795-04-5
Acetic acid (E)-(6R,7S)-6-hydroxy-7-(methoxy-methyl-carbamoyl)-3-methyl-oct-2-enyl ester

: 233256-51-4
(+)-FR182877

Guidance literature:: Multi-step reaction with 13 steps

1: 96 percent / imidazole / CH₂Cl₂

2: 85 percent / Pd₂dba3; NMP; i-Pr₂NEt / LiCl / 1.33 h / 40 °C

3: 81 percent / LDA / diethyl ether / -78 - 20 °C

4: 86 percent / TBAF / tetrahydrofuran / -40 - 0 °C

5: 93 percent / pyridine / CH₂Cl₂

6: 95 percent / imidazole / CH₂Cl₂

7: 80 percent / Pd₂dba3 / tetrahydrofuran / 12 h / 40 °C

8: 91 percent / KHMDS / tetrahydrofuran / -10 °C

9: mCPBA / CH₂Cl₂ / -40 °C

10: CHCl₃ / 4 h / 40 °C

11: PPTS / methanol

12: TFA / CH₂Cl₂ / 0 - 20 °C

13: EDC; DMAP / CH₂Cl₂

With pyridine; 1H-imidazole; 1-methyl-pyrrolidin-2-one; dmap; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; potassium hexamethylsilazane; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; lithium diisopropyl amide; lithium chloride; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; chloroform; 2: Stille coupling / 10: double transannular Diels-Alder reaction;
DOI:10.1021/ja025885o