6-Hydroxysugiol

Base Information

• Chemical Name: 6-Hydroxysugiol
• CAS No.: 55898-07-2
• Molecular Formula: C₂₀H₂₈O₃
• Molecular Weight: 316.441
• Mol file: 55898-07-2.mol

Synonyms:

Chemical Property of 6-Hydroxysugiol

Chemical Property:

• Boiling Point: 478.1±45.0 °C(Predicted)
• PKA: 8.60±0.70(Predicted)
• Density: 1.116±0.06 g/cm3(Predicted)

Purity/Quality:

99% ^*data from raw suppliers

6-Hydroxysugiol ≥98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 6-Hydroxysugiol

There total 17 articles about 6-Hydroxysugiol 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: 70.0%

(4aS,10aS)-7-isopropyl-6-methoxy-1,1,4a-trimethyl-1,2,3,4,4a,10a-hexahydrophenanthrene (70614-86-7) → 6α-hydroxy-7-oxoferruginol (55898-07-2)

Guidance literature:

(4aS,10aS)-7-isopropyl-6-methoxy-1,1,4a-trimethyl-1,2,3,4,4a,10a-hexahydrophenanthrene; With 3,3-dimethyldioxirane; In dichloromethane; acetone; at 25 ℃; for 0.333333h;

With sodium thioethylate; In dichloromethane; N,N-dimethyl-formamide; acetone; at 90 ℃; for 8h;

DOI:10.1016/j.tetlet.2013.06.048

Reference yield: 60.0%

(4aS,10aS)-7-isopropyl-6-methoxy-1,1,4a-trimethyl-1,2,3,4,4a,10a-hexahydrophenanthrene (70614-86-7) → 6α-hydroxy-7-oxoferruginol (55898-07-2) + 6-Hydroxy-5,6-dehydrosugiol (140923-35-9)

Guidance literature:

(4aS,10aS)-7-isopropyl-6-methoxy-1,1,4a-trimethyl-1,2,3,4,4a,10a-hexahydrophenanthrene; With 3,3-dimethyldioxirane; In dichloromethane; acetone; at 25 ℃; for 1h;

With sodium thioethylate; In dichloromethane; N,N-dimethyl-formamide; acetone; at 90 ℃; for 8h;

DOI:10.1016/j.tetlet.2013.06.048

Reference yield:

(+)-(4aS,10aS)-6-acetyl-7-isopropyl-1,1,4a-trimethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthrene (79593-19-4) → 6α-hydroxy-7-oxoferruginol (55898-07-2) + 6-Hydroxy-5,6-dehydrosugiol (140923-35-9)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 3-chloro-benzenecarboperoxoic acid; toluene-4-sulfonic acid / 1,2-dichloro-ethane / 5 h / Reflux

2.1: potassium carbonate / dichloromethane; methanol / 2 h / 0 °C

3.1: lithium hydroxide / N,N-dimethyl-formamide / 4 h / 20 °C / Inert atmosphere

3.2: 0.75 h / 0 °C

4.1: chromium(VI) oxide; acetic acid / 4 h / 20 °C

5.1: sodium tetrahydroborate / methanol / 12 h / 20 °C / Inert atmosphere

6.1: methanesulfonyl chloride; triethylamine / dichloromethane / 12 h / 0 °C / Inert atmosphere

7.1: 3,3-dimethyldioxirane / dichloromethane; acetone / 1 h / 25 °C

7.2: 8 h / 90 °C

With chromium(VI) oxide; sodium tetrahydroborate; 3,3-dimethyldioxirane; potassium carbonate; toluene-4-sulfonic acid; acetic acid; methanesulfonyl chloride; triethylamine; 3-chloro-benzenecarboperoxoic acid; lithium hydroxide; In methanol; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetone; 1.1: |Baeyer-Villiger Ketone Oxidation;

DOI:10.1016/j.tetlet.2013.06.048

upstream raw materials:

(+)-(4aS,10aS)-6-acetyl-7-isopropyl-1,1,4a-trimethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthrene

ar-abietatriene

ferruginol acetate

ferruginol