(3R,4R)-4-benzyloxy-2-(4'-methoxy)phenoxymethyl-6,7-methylenedioxy-3-triisopropylsilyloxymethyl-3,4-dihydronaphthalene

Base Information

Chemical Name:(3R,4R)-4-benzyloxy-2-(4'-methoxy)phenoxymethyl-6,7-methylenedioxy-3-triisopropylsilyloxymethyl-3,4-dihydronaphthalene
CAS No.:261158-23-0
Molecular Formula:C₃₆H₄₆O₆Si
Molecular Weight:602.843
Hs Code.:

Synonyms:(3R,4R)-4-benzyloxy-2-(4'-methoxy)phenoxymethyl-6,7-methylenedioxy-3-triisopropylsilyloxymethyl-3,4-dihydronaphthalene

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Chemical Property of (3R,4R)-4-benzyloxy-2-(4'-methoxy)phenoxymethyl-6,7-methylenedioxy-3-triisopropylsilyloxymethyl-3,4-dihydronaphthalene

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Technology Process of (3R,4R)-4-benzyloxy-2-(4'-methoxy)phenoxymethyl-6,7-methylenedioxy-3-triisopropylsilyloxymethyl-3,4-dihydronaphthalene

There total 15 articles about (3R,4R)-4-benzyloxy-2-(4'-methoxy)phenoxymethyl-6,7-methylenedioxy-3-triisopropylsilyloxymethyl-3,4-dihydronaphthalene 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: 28.0%

: 150-76-5
4-methoxy-phenol

: 261158-33-2
(3R,4R)-4-benzyloxy-2-hydroxymethyl-6,7-methylenedioxy-3-triisopropylsilyloxymethyl-3,4-dihydronaphthalene

: 261158-23-0
(3R,4R)-4-benzyloxy-2-(4'-methoxy)phenoxymethyl-6,7-methylenedioxy-3-triisopropylsilyloxymethyl-3,4-dihydronaphthalene

Guidance literature:: With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 80 ℃; for 13h;
DOI:10.1021/jo991582+

Reference yield:

: 74879-22-4
6-bromobenzo-1,3-dioxole-5-carboxaldehyde dimethyl acetal

: 261158-23-0
(3R,4R)-4-benzyloxy-2-(4'-methoxy)phenoxymethyl-6,7-methylenedioxy-3-triisopropylsilyloxymethyl-3,4-dihydronaphthalene

Guidance literature:: Multi-step reaction with 14 steps

1: 61 percent / n-BuLi / tetrahydrofuran; hexane / 2 h / -78 - 20 °C

2: 83 percent / NaBH₄ / ethanol / 20 °C

3: 90 percent / acetic acid / 2 h / 80 °C

4: 99 percent / H₂ / 10percent Pd/C / ethyl acetate / 6 h / 2482.38 Torr

5: 82 percent / LiAlH₄ / diethyl ether / 24 h / Heating

6: 100 percent / DMAP / pyridine / 16 h / 20 °C

7: 66 percent / PPL / dimethylsulfoxide; aq. phosphate buffer / 2.5 h / 20 °C / pH 7.8

8: 100 percent / imidazole / dimethylformamide / 7 h / 20 °C

9: 100 percent / K₂CO₃ / methanol / 1.5 h / 20 °C

10: 100 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / -78 - -40 °C

11: 90 percent / NaOMe / methanol / 20 °C

12: 100 percent / NaH / dimethylformamide / -10 - 20 °C

13: 87 percent / NaB(OCH₃)3H / ethanol / 9 h / 0 - 20 °C

14: 28 percent / PPh₃; DEAD / tetrahydrofuran / 13 h / 80 °C

With 1H-imidazole; dmap; sodium tetrahydroborate; lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; hydrogen; sodium methylate; sodium trimethoxyborohydride; sodium hydride; potassium carbonate; dimethyl sulfoxide; triethylamine; triphenylphosphine; diethylazodicarboxylate; 10percent Pd/C; In tetrahydrofuran; pyridine; methanol; phosphate buffer; diethyl ether; ethanol; hexane; dichloromethane; acetic acid; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; 1: Formylation / 2: Reduction / 3: Cycloaddition / 4: Catalytic hydrogenation / 5: Reduction / 6: Acetylation / 7: Deacetylation / 8: silylation / 9: Deacetylation / 10: Oxidation / 11: Ring cleavage / 12: Alkylation / 13: Reduction / 14: Etherification;
DOI:10.1021/jo991582+

Reference yield:

: 87850-43-9
4-(dimethoxy)methyl-5-formyl(1,2-methylenedioxy)benzene

: 261158-23-0
(3R,4R)-4-benzyloxy-2-(4'-methoxy)phenoxymethyl-6,7-methylenedioxy-3-triisopropylsilyloxymethyl-3,4-dihydronaphthalene

Guidance literature:: Multi-step reaction with 13 steps

1: 83 percent / NaBH₄ / ethanol / 20 °C

2: 90 percent / acetic acid / 2 h / 80 °C

3: 99 percent / H₂ / 10percent Pd/C / ethyl acetate / 6 h / 2482.38 Torr

4: 82 percent / LiAlH₄ / diethyl ether / 24 h / Heating

5: 100 percent / DMAP / pyridine / 16 h / 20 °C

6: 66 percent / PPL / dimethylsulfoxide; aq. phosphate buffer / 2.5 h / 20 °C / pH 7.8

7: 100 percent / imidazole / dimethylformamide / 7 h / 20 °C

8: 100 percent / K₂CO₃ / methanol / 1.5 h / 20 °C

9: 100 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / -78 - -40 °C

10: 90 percent / NaOMe / methanol / 20 °C

11: 100 percent / NaH / dimethylformamide / -10 - 20 °C

12: 87 percent / NaB(OCH₃)3H / ethanol / 9 h / 0 - 20 °C

13: 28 percent / PPh₃; DEAD / tetrahydrofuran / 13 h / 80 °C

With 1H-imidazole; dmap; sodium tetrahydroborate; lithium aluminium tetrahydride; oxalyl dichloride; hydrogen; sodium methylate; sodium trimethoxyborohydride; sodium hydride; potassium carbonate; dimethyl sulfoxide; triethylamine; triphenylphosphine; diethylazodicarboxylate; 10percent Pd/C; In tetrahydrofuran; pyridine; methanol; phosphate buffer; diethyl ether; ethanol; dichloromethane; acetic acid; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; 1: Reduction / 2: Cycloaddition / 3: Catalytic hydrogenation / 4: Reduction / 5: Acetylation / 6: Deacetylation / 7: silylation / 8: Deacetylation / 9: Oxidation / 10: Ring cleavage / 11: Alkylation / 12: Reduction / 13: Etherification;
DOI:10.1021/jo991582+