3-((2S,4aS,5aR,6aS,8R,9S,10aR,11aS,12aR)-9-Hydroxy-5a,6a,8-trimethyl-2-phenyl-dodecahydro-1,3,5,7,11-pentaoxa-naphthacen-8-yl)-propionic acid

Base Information

Chemical Name:3-((2S,4aS,5aR,6aS,8R,9S,10aR,11aS,12aR)-9-Hydroxy-5a,6a,8-trimethyl-2-phenyl-dodecahydro-1,3,5,7,11-pentaoxa-naphthacen-8-yl)-propionic acid
CAS No.:361535-09-3
Molecular Formula:C₂₅H₃₄O₈
Molecular Weight:462.54
Hs Code.:

Synonyms:3-((2S,4aS,5aR,6aS,8R,9S,10aR,11aS,12aR)-9-Hydroxy-5a,6a,8-trimethyl-2-phenyl-dodecahydro-1,3,5,7,11-pentaoxa-naphthacen-8-yl)-propionic acid

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Chemical Property of 3-((2S,4aS,5aR,6aS,8R,9S,10aR,11aS,12aR)-9-Hydroxy-5a,6a,8-trimethyl-2-phenyl-dodecahydro-1,3,5,7,11-pentaoxa-naphthacen-8-yl)-propionic acid

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Technology Process of 3-((2S,4aS,5aR,6aS,8R,9S,10aR,11aS,12aR)-9-Hydroxy-5a,6a,8-trimethyl-2-phenyl-dodecahydro-1,3,5,7,11-pentaoxa-naphthacen-8-yl)-propionic acid

There total 24 articles about 3-((2S,4aS,5aR,6aS,8R,9S,10aR,11aS,12aR)-9-Hydroxy-5a,6a,8-trimethyl-2-phenyl-dodecahydro-1,3,5,7,11-pentaoxa-naphthacen-8-yl)-propionic acid 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:

: 361535-07-1
3-((2S,4aS,5aR,6aS,8R,9S,10aR,11aS,12aR)-9-Hydroxy-5a,6a,8-trimethyl-2-phenyl-dodecahydro-1,3,5,7,11-pentaoxa-naphthacen-8-yl)-propionic acid methyl ester

: 361535-09-3
3-((2S,4aS,5aR,6aS,8R,9S,10aR,11aS,12aR)-9-Hydroxy-5a,6a,8-trimethyl-2-phenyl-dodecahydro-1,3,5,7,11-pentaoxa-naphthacen-8-yl)-propionic acid

Guidance literature:: With lithium hydroxide; In methanol; water; at 20 ℃; for 3.5h;
DOI:10.1021/ol016355k

Reference yield:

: 361534-73-8
(2S,4aS,6R,7S,8aR)-6-Hydroxymethyl-6-methyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol

: 361535-09-3
3-((2S,4aS,5aR,6aS,8R,9S,10aR,11aS,12aR)-9-Hydroxy-5a,6a,8-trimethyl-2-phenyl-dodecahydro-1,3,5,7,11-pentaoxa-naphthacen-8-yl)-propionic acid

Guidance literature:: Multi-step reaction with 22 steps

1.1: 2,6-lutidine / CH₂Cl₂ / 1 h / -78 °C

2.1: CH₂Cl₂ / 3 h / -78 - 0 °C

3.1: 1.33 g / molecular sieves 4 A / dimethylsulfoxide / 0.67 h / 80 °C

4.1: 87 percent / DIBAH / CH₂Cl₂; hexane / 1 h / -78 °C

5.1: 89 percent / tetrahydrofuran / 1 h / 0 - 20 °C

6.1: N-methylmorpholine N-oxide; molecular sieves 4 A / CH₂Cl₂ / 0.75 h / 20 °C

6.2: 93 percent / tetrapropylammonium perruthenate / CH₂Cl₂ / 1.5 h / 20 °C

7.1: 487 mg / n-Bu₄NF*xH₂O / tetrahydrofuran / 2.5 h / 20 °C

8.1: 544 mg / N-methylmorpholine / CH₂Cl₂ / 6 h / 20 °C

9.1: 99 percent / SmI₂ / methanol; tetrahydrofuran / 0.08 h / 0 °C

10.1: 97 percent / 2,6-lutidine / CH₂Cl₂ / 0.25 h / 0 °C

11.1: 513 mg / DIBAH / toluene; hexane / 0.25 h / -78 °C

12.1: 565 mg / toluene / 100 °C

13.1: 480 mg / DIBAH / toluene; hexane / 0.17 h / -78 °C

14.1: (+)-diethyl L-tartrate; Ti(O-i-Pr)4 / CH₂Cl₂ / 0.33 h / -20 °C

14.2: 100 percent / t-BuOOH / CH₂Cl₂ / 22 h / -20 °C

15.1: N-methylmorpholine N-oxide; molecular sieves 4 A / CH₂Cl₂ / 0.25 h / 20 °C

15.2: 56.2 mg / tetrapropylammonium perruthenate / CH₂Cl₂ / 0.5 h / 20 °C

16.1: NaN(TMS)2 / tetrahydrofuran / 0.33 h / 0 °C

16.2: 42.8 mg / tetrahydrofuran / 0.25 h / 0 °C

17.1: 99 percent / n-Bu₄NF / tetrahydrofuran / 0.5 h / 20 °C

18.1: 74 percent / 10-camphorsulfonic acid / toluene / 3.5 h / 0 °C

19.1: O₃ / CH₂Cl₂ / 0.02 h / -78 °C

20.1: 11.5 mg / toluene / 1 h / 100 °C

21.1: H₂ / Pd/C / ethyl acetate / 2 h / 20 °C

22.1: LiOH / methanol; H₂O / 3.5 h / 20 °C

With 4-methyl-morpholine; 2,6-dimethylpyridine; titanium(IV) isopropylate; lithium hydroxide; samarium diiodide; diethyl (2R,3R)-tartrate; 4 A molecular sieve; (1S)-10-camphorsulfonic acid; tetrabutyl ammonium fluoride; hydrogen; sodium hexamethyldisilazane; diisobutylaluminium hydride; ozone; 4-methylmorpholine N-oxide; palladium on activated charcoal; In tetrahydrofuran; methanol; hexane; dichloromethane; water; dimethyl sulfoxide; ethyl acetate; toluene; 5.1: Grignard reaction / 8.1: hetero-Michael reaction / 12.1: Wittig reaction / 16.2: Wittig reaction / 20.1: Wittig reaction;
DOI:10.1021/ol016355k

Reference yield:

: 1053634-48-2
(2S,4R,5S)-4-((2S,3S)-3-Hydroxymethyl-3-methyl-oxiranylmethyl)-2-phenyl-[1,3]dioxan-5-ol

: 361535-09-3
3-((2S,4aS,5aR,6aS,8R,9S,10aR,11aS,12aR)-9-Hydroxy-5a,6a,8-trimethyl-2-phenyl-dodecahydro-1,3,5,7,11-pentaoxa-naphthacen-8-yl)-propionic acid

Guidance literature:: Multi-step reaction with 23 steps

1.1: 100 percent / PPTS / CH₂Cl₂ / 20 °C

2.1: 2,6-lutidine / CH₂Cl₂ / 1 h / -78 °C

3.1: CH₂Cl₂ / 3 h / -78 - 0 °C

4.1: 1.33 g / molecular sieves 4 A / dimethylsulfoxide / 0.67 h / 80 °C

5.1: 87 percent / DIBAH / CH₂Cl₂; hexane / 1 h / -78 °C

6.1: 89 percent / tetrahydrofuran / 1 h / 0 - 20 °C

7.1: N-methylmorpholine N-oxide; molecular sieves 4 A / CH₂Cl₂ / 0.75 h / 20 °C

7.2: 93 percent / tetrapropylammonium perruthenate / CH₂Cl₂ / 1.5 h / 20 °C

8.1: 487 mg / n-Bu₄NF*xH₂O / tetrahydrofuran / 2.5 h / 20 °C

9.1: 544 mg / N-methylmorpholine / CH₂Cl₂ / 6 h / 20 °C

10.1: 99 percent / SmI₂ / methanol; tetrahydrofuran / 0.08 h / 0 °C

11.1: 97 percent / 2,6-lutidine / CH₂Cl₂ / 0.25 h / 0 °C

12.1: 513 mg / DIBAH / toluene; hexane / 0.25 h / -78 °C

13.1: 565 mg / toluene / 100 °C

14.1: 480 mg / DIBAH / toluene; hexane / 0.17 h / -78 °C

15.1: (+)-diethyl L-tartrate; Ti(O-i-Pr)4 / CH₂Cl₂ / 0.33 h / -20 °C

15.2: 100 percent / t-BuOOH / CH₂Cl₂ / 22 h / -20 °C

16.1: N-methylmorpholine N-oxide; molecular sieves 4 A / CH₂Cl₂ / 0.25 h / 20 °C

16.2: 56.2 mg / tetrapropylammonium perruthenate / CH₂Cl₂ / 0.5 h / 20 °C

17.1: NaN(TMS)2 / tetrahydrofuran / 0.33 h / 0 °C

17.2: 42.8 mg / tetrahydrofuran / 0.25 h / 0 °C

18.1: 99 percent / n-Bu₄NF / tetrahydrofuran / 0.5 h / 20 °C

19.1: 74 percent / 10-camphorsulfonic acid / toluene / 3.5 h / 0 °C

20.1: O₃ / CH₂Cl₂ / 0.02 h / -78 °C

21.1: 11.5 mg / toluene / 1 h / 100 °C

22.1: H₂ / Pd/C / ethyl acetate / 2 h / 20 °C

23.1: LiOH / methanol; H₂O / 3.5 h / 20 °C

With 4-methyl-morpholine; 2,6-dimethylpyridine; titanium(IV) isopropylate; lithium hydroxide; samarium diiodide; diethyl (2R,3R)-tartrate; 4 A molecular sieve; (1S)-10-camphorsulfonic acid; tetrabutyl ammonium fluoride; hydrogen; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; ozone; 4-methylmorpholine N-oxide; palladium on activated charcoal; In tetrahydrofuran; methanol; hexane; dichloromethane; water; dimethyl sulfoxide; ethyl acetate; toluene; 6.1: Grignard reaction / 9.1: hetero-Michael reaction / 13.1: Wittig reaction / 17.2: Wittig reaction / 21.1: Wittig reaction;
DOI:10.1021/ol016355k