1-((3aR,8aS)-2,2-Dimethyl-8,8a-dihydro-3aH-indeno[1,2-d]oxazol-3-yl)-2-[(2R,4S,5R)-2-(4-methoxy-phenyl)-4-vinyl-[1,3]dioxan-5-yloxy]-ethanone

Base Information

• Chemical Name: 1-((3aR,8aS)-2,2-Dimethyl-8,8a-dihydro-3aH-indeno[1,2-d]oxazol-3-yl)-2-[(2R,4S,5R)-2-(4-methoxy-phenyl)-4-vinyl-[1,3]dioxan-5-yloxy]-ethanone
• CAS No.: 357439-31-7
• Molecular Formula: C₂₇H₃₁NO₆
• Molecular Weight: 465.546
• Mol file: 357439-31-7.mol

Synonyms:1-((3aR,8aS)-2,2-Dimethyl-8,8a-dihydro-3aH-indeno[1,2-d]oxazol-3-yl)-2-[(2R,4S,5R)-2-(4-methoxy-phenyl)-4-vinyl-[1,3]dioxan-5-yloxy]-ethanone

Chemical Property of 1-((3aR,8aS)-2,2-Dimethyl-8,8a-dihydro-3aH-indeno[1,2-d]oxazol-3-yl)-2-[(2R,4S,5R)-2-(4-methoxy-phenyl)-4-vinyl-[1,3]dioxan-5-yloxy]-ethanone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-((3aR,8aS)-2,2-Dimethyl-8,8a-dihydro-3aH-indeno[1,2-d]oxazol-3-yl)-2-[(2R,4S,5R)-2-(4-methoxy-phenyl)-4-vinyl-[1,3]dioxan-5-yloxy]-ethanone

There total 2 articles about 1-((3aR,8aS)-2,2-Dimethyl-8,8a-dihydro-3aH-indeno[1,2-d]oxazol-3-yl)-2-[(2R,4S,5R)-2-(4-methoxy-phenyl)-4-vinyl-[1,3]dioxan-5-yloxy]-ethanone 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: 98.0%

2-bromo-1-(2,2-dimethyl-8,8a-dihydro-3aH-indeno[1,2-d]oxazol-3-yl)-ethanone (776315-69-6) + (2R,4S,5R)-2-(4-Methoxy-phenyl)-4-vinyl-[1,3]dioxan-5-ol (440320-33-2) → 1-((3aR,8aS)-2,2-Dimethyl-8,8a-dihydro-3aH-indeno[1,2-d]oxazol-3-yl)-2-[(2R,4S,5R)-2-(4-methoxy-phenyl)-4-vinyl-[1,3]dioxan-5-yloxy]-ethanone (357439-31-7)

Guidance literature:

With sodium hydride; In tetrahydrofuran; N,N-dimethyl-formamide; at 20 ℃; for 5h;

DOI:10.1016/j.tet.2004.07.010

Reference yield:

(1R,2S)-1-Amino-2-indanol (136030-00-7) → 1-((3aR,8aS)-2,2-Dimethyl-8,8a-dihydro-3aH-indeno[1,2-d]oxazol-3-yl)-2-[(2R,4S,5R)-2-(4-methoxy-phenyl)-4-vinyl-[1,3]dioxan-5-yloxy]-ethanone (357439-31-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: Et₃N / tetrahydrofuran / 2 h / 20 °C

1.2: (1S)-(+)-10-camphorsulfonic acid / tetrahydrofuran / 2 h / 20 °C

2.1: 98 percent / NaH / tetrahydrofuran; dimethylformamide / 5 h / 20 °C

With sodium hydride; triethylamine; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1016/j.tet.2004.07.010

Reference yield:

1-((3aR,8aS)-2,2-Dimethyl-8,8a-dihydro-3aH-indeno[1,2-d]oxazol-3-yl)-2-[(2R,4S,5R)-2-(4-methoxy-phenyl)-4-vinyl-[1,3]dioxan-5-yloxy]-ethanone (357439-31-7) → C40H42O9

Guidance literature:

Multi-step reaction with 29 steps

1.1: nBuLi / tetrahydrofuran; hexane / -78 °C

1.2: 47.4 g / N,N'-dimethylpropyleneurea / tetrahydrofuran / 18 h / -78 - 20 °C

2.1: 21.0 g / pyridinium p-toluenesulfonate / propan-1-ol / 16 h / 20 °C

3.1: 91 percent / 2,6-lutidine / CH₂Cl₂ / 2 h / 0 °C

4.1: 70 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH₂Cl₂; H₂O / 2.5 h / -5 °C

5.1: 1.58 g / (1S)-(+)-10-camphorsulfonic acid; p-anisaldehyde / toluene / 90 °C

6.1: MeLi / diethyl ether / 0.5 h / -78 °C

6.2: 1.31 g / tetrahydrofuran; diethyl ether / 0.75 h / -100 - -90 °C

7.1: Et₃SiH / acetonitrile / 0.67 h / -40 - -20 °C

7.2: 58 percent / tetrabutylammonium fluoride / tetrahydrofuran / 44 h / 20 °C

8.1: 99 percent / Grubbs catalyst / CH₂Cl₂ / 2.5 h / 20 °C

9.1: 97 percent / AlCl₃ / CH₂Cl₂; nitromethane / 0.33 h / 0 °C

10.1: 84 percent / pyridinium p-toluenesulfonate / dimethylformamide; CH₂Cl₂ / 13 h / 20 °C

11.1: 88 percent / NaH; tetrabutylammonium iodide / dimethylformamide; tetrahydrofuran / 0.5 h / 40 °C

12.1: 1.11 g / TsOH*H₂O / methanol; tetrahydrofuran / 27 h / 20 °C

13.1: 1.52 g / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C

14.1: 85 percent / (1S)-(+)-10-camphorsulfonic acid / methanol; tetrahydrofuran / 14 h / -15 °C

15.1: 96 percent / molecular sieves 4 Angstroem / pyridine / 24 h / 20 °C

16.1: 94 percent / dimethylsulfoxide / 20 h / 50 °C

17.1: diisobutylaluminum hydride / CH₂Cl₂; hexane / 3 h / -70 °C

17.2: Rochelle salt solution / CH₂Cl₂ / 2 h / 20 °C

18.1: 481 mg / NaN(SiMe₃)2 / tetrahydrofuran / 1 h / 0 °C

19.1: 91 percent / tetrabutylammonium fluoride / tetrahydrofuran / 18 h / 20 °C

20.1: 92 percent / NaH / tetrahydrofuran; dimethylformamide / 10 h / 20 °C

21.1: 81 percent / HCl / tetrahydrofuran / 23 h / 30 °C

22.1: Et₃N / CH₂Cl₂ / 1 h / 0 °C

23.1: n-BuLi / tetrahydrofuran; hexane / 0.25 h / -78 °C

23.2: 87.4 mg / tetrahydrofuran; hexane; CH₂Cl₂ / -78 - 0 °C

24.1: 72 percent / TiCl₄; Et₃N / CH₂Cl₂ / 0.33 h / -78 °C

25.1: 99 percent / NaBH₄ / tetrahydrofuran; H₂O

26.1: 92 percent / Grubbs catalyst / CH₂Cl₂ / 1 h / 20 °C

27.1: 83 percent / imidazole / CH₂Cl₂ / 0.5 h / 20 °C

28.1: 100 percent / PPh₃; diethyl azodicarboxylate / toluene / 0.33 h / 20 °C

29.1: 92 percent / tetrabutylammonium fluoride / tetrahydrofuran / 3 h / 20 °C

With 1H-imidazole; 2,6-dimethylpyridine; hydrogenchloride; triethylsilane; sodium tetrahydroborate; n-butyllithium; aluminium trichloride; 4 A molecular sieve; tetrabutyl ammonium fluoride; methyllithium; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; titanium tetrachloride; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; 4-methoxy-benzaldehyde; toluene-4-sulfonic acid; (+)-10-camphorsulfonic acid; triethylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; diethylazodicarboxylate; Grubbs catalyst first generation; In tetrahydrofuran; pyridine; methanol; propan-1-ol; diethyl ether; nitromethane; hexane; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; acetonitrile; 24.1: aldol reaction / 28.1: Mitsunobu reaction;

DOI:10.1016/j.tet.2004.07.010

upstream raw materials:

2-bromo-1-(2,2-dimethyl-8,8a-dihydro-3aH-indeno[1,2-d]oxazol-3-yl)-ethanone

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

(1R,2S)-1-Amino-2-indanol

Downstream raw materials:

3-[4-benzyloxy-3-(4-methoxy-benzyloxy)-3,4,4a,6,9,9a-hexahydro-2H-1,5-dioxa-benzocyclohepten-2-yl]-1-(2,2-dimethyl-8,8a-dihydro-3aH-indeno[1,2-d]oxazol-3-yl)-2-[2-(4-methoxy-phenyl)-4-vinyl-[1,3]dioxan-5-yloxy]-propan-1-one

C₄₀H₄₄O₇S

C₄₁H₅₂O₉SSi

C₄₂H₄₅NO₉