(2R,4aR,5aS,7R,8S,9aR,11aS)-8-Methyl-2-phenyl-8-vinyl-decahydro-1,3,5,9-tetraoxa-dibenzo[a,d]cyclohepten-7-ol

Base Information

Chemical Name:(2R,4aR,5aS,7R,8S,9aR,11aS)-8-Methyl-2-phenyl-8-vinyl-decahydro-1,3,5,9-tetraoxa-dibenzo[a,d]cyclohepten-7-ol
CAS No.:486394-70-1
Molecular Formula:C₂₀H₂₆O₅
Molecular Weight:346.423
Hs Code.:

Synonyms:(2R,4aR,5aS,7R,8S,9aR,11aS)-8-Methyl-2-phenyl-8-vinyl-decahydro-1,3,5,9-tetraoxa-dibenzo[a,d]cyclohepten-7-ol

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Chemical Property of (2R,4aR,5aS,7R,8S,9aR,11aS)-8-Methyl-2-phenyl-8-vinyl-decahydro-1,3,5,9-tetraoxa-dibenzo[a,d]cyclohepten-7-ol

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Technology Process of (2R,4aR,5aS,7R,8S,9aR,11aS)-8-Methyl-2-phenyl-8-vinyl-decahydro-1,3,5,9-tetraoxa-dibenzo[a,d]cyclohepten-7-ol

There total 16 articles about (2R,4aR,5aS,7R,8S,9aR,11aS)-8-Methyl-2-phenyl-8-vinyl-decahydro-1,3,5,9-tetraoxa-dibenzo[a,d]cyclohepten-7-ol 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:

: (2R,4aR,6S,7R,9aS)-6-((2R,3R)-3-Methyl-3-vinyl-oxiranylmethyl)-2-phenyl-hexahydro-1,3,5-trioxa-benzocyclohepten-7-ol

: 486394-70-1
(2R,4aR,5aS,7R,8S,9aR,11aS)-8-Methyl-2-phenyl-8-vinyl-decahydro-1,3,5,9-tetraoxa-dibenzo[a,d]cyclohepten-7-ol

Guidance literature:: With pyridinium p-toluenesulfonate; In dichloromethane; at 20 ℃; for 1.5h;
DOI:10.1021/ja028167a

Reference yield:

: (3aS,4aR,7R,8aS,10aR)-7-Phenyl-octahydro-1,4,6,8-tetraoxa-benzo[f]azulen-2-ol

: 486394-70-1
(2R,4aR,5aS,7R,8S,9aR,11aS)-8-Methyl-2-phenyl-8-vinyl-decahydro-1,3,5,9-tetraoxa-dibenzo[a,d]cyclohepten-7-ol

Guidance literature:: Multi-step reaction with 8 steps

1.1: 5.93 g / toluene / 20 - 80 °C

2.1: 100 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

3.1: 100 percent / DIBALH / CH₂Cl₂; hexane / 0.5 h / -78 °C

4.1: (-)-diethyl tartrate; Ti(Oi-Pr)4; 4 Angstroem molecular sieves / CH₂Cl₂ / 0.5 h / -20 °C

4.2: 97 percent / t-BuOOH / CH₂Cl₂; 2,2,4-trimethyl-pentane / -20 °C

5.1: SO₃*pyridine; Et₃N / dimethylsulfoxide; CH₂Cl₂ / 0.5 h / 0 °C

6.1: NaHMDS / tetrahydrofuran / 1 h / 0 °C

6.2: 122.2 mg / tetrahydrofuran / 0.5 h / 0 °C

7.1: tetra-n-butylammonium fluoride / tetrahydrofuran / 0.83 h / 20 °C

8.1: 3.00 g / pyridinium p-toluenesulfonate / CH₂Cl₂ / 1.5 h / 20 °C

With 2,6-dimethylpyridine; titanium(IV) isopropylate; pyridine-SO₃ complex; 4 A molecular sieve; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; (-)-diethyl tartrate; triethylamine; In tetrahydrofuran; hexane; dichloromethane; dimethyl sulfoxide; toluene; 1.1: Wittig reaction / 4.1: Sharpless asymmetric epoxidation / 6.1: Wittig methylenation;
DOI:10.1021/ja028167a

Reference yield:

: 221455-78-3
2-[(2R,4S,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-2-phenyl-[1,3]dioxan-4-yl]-ethanol

: 486394-70-1
(2R,4aR,5aS,7R,8S,9aR,11aS)-8-Methyl-2-phenyl-8-vinyl-decahydro-1,3,5,9-tetraoxa-dibenzo[a,d]cyclohepten-7-ol

Guidance literature:: Multi-step reaction with 15 steps

1.1: 99 percent / I₂; PPh₃; imidazole / tetrahydrofuran / 0.33 h / 20 °C

2.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -20 °C

2.2: tetrahydrofuran; hexane / 1.17 h / -20 - 0 °C

3.1: 122.7 mg / tetra-butylammonium fluoride / tetrahydrofuran / 1.5 h / 20 °C

4.1: N-methylmorpholine / CH₂Cl₂ / 20 °C

5.1: 12.43 g / NaHCO₃ / acetonitrile; H₂O / 20 °C

6.1: 70 percent / SmI₂; methanol / tetrahydrofuran / 0.08 h / 20 °C

7.1: DIBALH / CH₂Cl₂; hexane / 1 h / -78 °C

8.1: 5.93 g / toluene / 20 - 80 °C

9.1: 100 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

10.1: 100 percent / DIBALH / CH₂Cl₂; hexane / 0.5 h / -78 °C

11.1: (-)-diethyl tartrate; Ti(Oi-Pr)4; 4 Angstroem molecular sieves / CH₂Cl₂ / 0.5 h / -20 °C

11.2: 97 percent / t-BuOOH / CH₂Cl₂; 2,2,4-trimethyl-pentane / -20 °C

12.1: SO₃*pyridine; Et₃N / dimethylsulfoxide; CH₂Cl₂ / 0.5 h / 0 °C

13.1: NaHMDS / tetrahydrofuran / 1 h / 0 °C

13.2: 122.2 mg / tetrahydrofuran / 0.5 h / 0 °C

14.1: tetra-n-butylammonium fluoride / tetrahydrofuran / 0.83 h / 20 °C

15.1: 3.00 g / pyridinium p-toluenesulfonate / CH₂Cl₂ / 1.5 h / 20 °C

With 4-methyl-morpholine; 1H-imidazole; 2,6-dimethylpyridine; titanium(IV) isopropylate; methanol; n-butyllithium; samarium diiodide; pyridine-SO₃ complex; 4 A molecular sieve; tetrabutyl ammonium fluoride; iodine; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; sodium hydrogencarbonate; (-)-diethyl tartrate; triethylamine; triphenylphosphine; In tetrahydrofuran; hexane; dichloromethane; water; dimethyl sulfoxide; toluene; acetonitrile; 8.1: Wittig reaction / 11.1: Sharpless asymmetric epoxidation / 13.1: Wittig methylenation;
DOI:10.1021/ja028167a