(7R,8S,8aS,9aR)-5-methyl-7,8,8a,9a-tetrahydrochryseno[3,4-b]oxirene-7,8-diol

Base Information

• Chemical Name: (7R,8S,8aS,9aR)-5-methyl-7,8,8a,9a-tetrahydrochryseno[3,4-b]oxirene-7,8-diol
• CAS No.: 111901-41-8
• Molecular Formula: C₁₉H₁₆O₃
• Molecular Weight: 292.334
• Mol file: 111901-41-8.mol

Synonyms:

Chemical Property of (7R,8S,8aS,9aR)-5-methyl-7,8,8a,9a-tetrahydrochryseno[3,4-b]oxirene-7,8-diol

Chemical Property:

• Vapor Pressure: 7.33E-14mmHg at 25°C
• Boiling Point: 570.6°Cat760mmHg
• Flash Point: 298.9°C
• Density: 1.429g/cm³

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (7R,8S,8aS,9aR)-5-methyl-7,8,8a,9a-tetrahydrochryseno[3,4-b]oxirene-7,8-diol

There total 18 articles about (7R,8S,8aS,9aR)-5-methyl-7,8,8a,9a-tetrahydrochryseno[3,4-b]oxirene-7,8-diol 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: 76.0%

9α-bromo-7β,8α,10β-trihydroxy-7,8,9,10-tetrahydro-5-methylchrysene (101349-65-9) → trans-7,8-dihydroxy-syn-9,10-epoxy-5-methyl-7,8,9,10-tetrahydrochrysene (81851-67-4,96790-41-9,97170-08-6,98508-99-7,111901-41-8,111901-42-9,111901-43-0)

Guidance literature:

With potassium tert-butylate; In tetrahydrofuran; tert-butyl alcohol; for 0.5h; Ambient temperature;

DOI:10.1021/jo00359a006

Reference yield:

7-oxo-7,8,9,10-tetrahydro-5-methylchrysene (27343-29-9) → trans-7,8-dihydroxy-syn-9,10-epoxy-5-methyl-7,8,9,10-tetrahydrochrysene (81851-67-4,96790-41-9,97170-08-6,98508-99-7,111901-41-8,111901-42-9,111901-43-0)

Guidance literature:

Multi-step reaction with 10 steps

1: NaBH₄ / tetrahydrofuran; methanol / 4.5 h

2: tosic acid / benzene / 1 h / Heating

3: 80 percent / I₂ / benzene / 4 h / Heating

4: 2.97 g / p-toluenesulfonic acid / benzene / 24 h / Heating

5: 71 percent / DDQ / benzene

6: 85 percent / glacial acetic acid, concd. HCl / 24 h / Heating

7: 82 percent / Adogen 464, Fremy's salt, KH₂PO₄ / H₂O / 1 h

8: 91 percent / NaBH₄, O₂ / ethanol / 28 h

9: 61 percent / N-bromosuccinimide / dimethylsulfoxide; H₂O / 1 h / Ambient temperature

10: 76 percent / potasium tert-butoxide / tetrahydrofuran; 2-methyl-propan-2-ol / 0.5 h / Ambient temperature

With hydrogenchloride; sodium tetrahydroborate; potassium dihydrogenphosphate; N-Bromosuccinimide; adogen 464; potassiuim nitrosodisulfonate; potassium tert-butylate; iodine; oxygen; toluene-4-sulfonic acid; acetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; methanol; ethanol; water; dimethyl sulfoxide; tert-butyl alcohol; benzene;

DOI:10.1021/jo00359a006

Reference yield:

11-methyl-1,2,3,4-tetrahydro-chrysen-1-ol (855169-42-5) → trans-7,8-dihydroxy-syn-9,10-epoxy-5-methyl-7,8,9,10-tetrahydrochrysene (81851-67-4,96790-41-9,97170-08-6,98508-99-7,111901-41-8,111901-42-9,111901-43-0)

Guidance literature:

Multi-step reaction with 9 steps

1: tosic acid / benzene / 1 h / Heating

2: 80 percent / I₂ / benzene / 4 h / Heating

3: 2.97 g / p-toluenesulfonic acid / benzene / 24 h / Heating

4: 71 percent / DDQ / benzene

5: 85 percent / glacial acetic acid, concd. HCl / 24 h / Heating

6: 82 percent / Adogen 464, Fremy's salt, KH₂PO₄ / H₂O / 1 h

7: 91 percent / NaBH₄, O₂ / ethanol / 28 h

8: 61 percent / N-bromosuccinimide / dimethylsulfoxide; H₂O / 1 h / Ambient temperature

9: 76 percent / potasium tert-butoxide / tetrahydrofuran; 2-methyl-propan-2-ol / 0.5 h / Ambient temperature

With hydrogenchloride; sodium tetrahydroborate; potassium dihydrogenphosphate; N-Bromosuccinimide; adogen 464; potassiuim nitrosodisulfonate; potassium tert-butylate; iodine; oxygen; toluene-4-sulfonic acid; acetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; ethanol; water; dimethyl sulfoxide; tert-butyl alcohol; benzene;

DOI:10.1021/jo00359a006

upstream raw materials:

9α-bromo-7β,8α,10β-trihydroxy-7,8,9,10-tetrahydro-5-methylchrysene

7-oxo-7,8,9,10-tetrahydro-5-methylchrysene

11-methyl-1,2,3,4-tetrahydro-chrysen-1-ol

5-methylchrysene-7,8-dione