(3R,4R,5R)-2-tert-butyl(diphenyl)silyloxy-1,4:3,5-diepoxy-1,2-seco-12-noreudesman-11-one

Base Information

Chemical Name:(3R,4R,5R)-2-tert-butyl(diphenyl)silyloxy-1,4:3,5-diepoxy-1,2-seco-12-noreudesman-11-one
CAS No.:548757-05-7
Molecular Formula:C₃₀H₄₀O₄Si
Molecular Weight:492.731
Hs Code.:

Synonyms:(3R,4R,5R)-2-tert-butyl(diphenyl)silyloxy-1,4:3,5-diepoxy-1,2-seco-12-noreudesman-11-one

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (3R,4R,5R)-2-tert-butyl(diphenyl)silyloxy-1,4:3,5-diepoxy-1,2-seco-12-noreudesman-11-one

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Technology Process of (3R,4R,5R)-2-tert-butyl(diphenyl)silyloxy-1,4:3,5-diepoxy-1,2-seco-12-noreudesman-11-one

There total 8 articles about (3R,4R,5R)-2-tert-butyl(diphenyl)silyloxy-1,4:3,5-diepoxy-1,2-seco-12-noreudesman-11-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: 79.0%

: 548757-17-1
1-[(2R,2aR,4aS,7R,8aR)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-2a,4a-dimethyl-octahydro-1,3-dioxa-cyclobuta[c]inden-7-yl]-ethanol

: 548757-05-7
(3R,4R,5R)-2-tert-butyl(diphenyl)silyloxy-1,4:3,5-diepoxy-1,2-seco-12-noreudesman-11-one

Guidance literature:: With sodium acetate; pyridinium chlorochromate; In dichloromethane; at 20 ℃; for 2h;
DOI:10.1021/jo034129d

Reference yield:

: 548757-15-9
(S)-2-((2R,2aR,4aS,7R,8aR)-2-Hydroxymethyl-2a,4a-dimethyl-octahydro-1,3-dioxa-cyclobuta[c]inden-7-yl)-propionic acid

: 548757-05-7
(3R,4R,5R)-2-tert-butyl(diphenyl)silyloxy-1,4:3,5-diepoxy-1,2-seco-12-noreudesman-11-one

Guidance literature:: Multi-step reaction with 6 steps

1: 173 mg / triethylamine; 4-(dimethylamino)pyridine / CH₂Cl₂ / 2.75 h / 20 °C

2: 82 percent / KOH / H₂O; methanol / 1 h / 20 °C

3: oxalyl chloride / dimethylformamide; benzene / 1 h / 20 °C

4: CH₂Cl₂ / 2 h / 20 °C

5: 115 mg / (PHS)3Sb; air / diethyl ether / 1.5 h / 20 °C

6: 79 percent / pyridinium chlorochromate; sodium acetate / CH₂Cl₂ / 2 h / 20 °C

With dmap; potassium hydroxide; oxalyl dichloride; air; sodium acetate; thiophenol; antimony tris-benzenethiolate; triethylamine; pyridinium chlorochromate; In methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; benzene; 5: Barton decarboxylation;
DOI:10.1021/jo034129d

Reference yield:

: 548756-89-4
methyl (3R,4R,5R,11S)-2-acetoxy-1,4:3,5-diepoxy-1,2-secoeudesman-13-oate

: 548757-05-7
(3R,4R,5R)-2-tert-butyl(diphenyl)silyloxy-1,4:3,5-diepoxy-1,2-seco-12-noreudesman-11-one

Guidance literature:: Multi-step reaction with 7 steps

1: KOH / H₂O; methanol / 23 h / 40 °C

2: 173 mg / triethylamine; 4-(dimethylamino)pyridine / CH₂Cl₂ / 2.75 h / 20 °C

3: 82 percent / KOH / H₂O; methanol / 1 h / 20 °C

4: oxalyl chloride / dimethylformamide; benzene / 1 h / 20 °C

5: CH₂Cl₂ / 2 h / 20 °C

6: 115 mg / (PHS)3Sb; air / diethyl ether / 1.5 h / 20 °C

7: 79 percent / pyridinium chlorochromate; sodium acetate / CH₂Cl₂ / 2 h / 20 °C

With dmap; potassium hydroxide; oxalyl dichloride; air; sodium acetate; thiophenol; antimony tris-benzenethiolate; triethylamine; pyridinium chlorochromate; In methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; benzene; 6: Barton decarboxylation;
DOI:10.1021/jo034129d