(+/-)8S,14-cedranediol

Base Information

• Chemical Name: (+/-)8S,14-cedranediol
• CAS No.: 97723-96-1
• Molecular Formula: C₁₅H₂₆O₂
• Molecular Weight: 238.37
• Mol file: 97723-96-1.mol

Synonyms:

Chemical Property of (+/-)8S,14-cedranediol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+/-)8S,14-cedranediol

There total 24 articles about (+/-)8S,14-cedranediol 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:

glutaric anhydride, (108-55-4) → (+/-)8S,14-cedranediol (18319-33-0,20315-41-7,62600-04-8,62600-05-9,88588-48-1,97723-96-1)

Guidance literature:

Multi-step reaction with 21 steps

1: 99 percent / pyridine / 48 h / 90 °C

2: Et₃N / tetrahydrofuran / 1.5 h / 0 °C

3: NaBH₄ / H₂O / 1 h / Ambient temperature

4: 77 percent / p-toluenesulfonic acid / CH₂Cl₂ / 2 h / Ambient temperature

5: 1) lithium cyclohexylisopropylamide; 2) Et₃N / 1) 30 min, -78 deg C, THF; 2) 30 min, -45 deg C

6: 6 h / 57 °C

7: aq. methanol / 10 h / Ambient temperature

8: 94 percent / LiAlH₄ / diethyl ether / 8 h / Ambient temperature

9: 90 percent / N,N-dimethylaniline / CH₂Cl₂ / 0.25 h / Ambient temperature

10: 86 percent / HCl / methanol / 2 h / Ambient temperature

11: 71 percent / PCC / CH₂Cl₂ / 1) 15 min; 2) 20 min, RT

12: 83 percent / CH₂Cl₂ / 16 h / Ambient temperature

13: 83 percent / hydroquinone / toluene / 24 h / 180 °C

15: 91.8 percent / pyridine / 96 h / Ambient temperature

16: 81.7 percent / LiAlH₄ / 1,2-dimethoxy-ethane / 48 h / Heating

17: 79 percent / MnO₂ / diethyl ether / 48 h

18: p-toluenesulfonic acid / CH₂Cl₂ / 1 h / Ambient temperature

19: ethanol / 1 h / Ambient temperature

20: H₂ / Pd-C / ethanol / 20 h / Ambient temperature

21: p-toluenesulfonic acid / ethanol / 1 h

With hydrogenchloride; methanol; manganese(IV) oxide; sodium tetrahydroborate; lithium aluminium tetrahydride; hydrogen; lithium cyclohexylisopropylamide; toluene-4-sulfonic acid; N,N-dimethyl-aniline; triethylamine; hydroquinone; pyridinium chlorochromate; palladium on activated charcoal; toluene-4-sulfonic acid; In tetrahydrofuran; pyridine; methanol; 1,2-dimethoxyethane; diethyl ether; ethanol; dichloromethane; water; toluene;

DOI:10.1016/S0040-4020(01)82444-3

Reference yield:

1SR,2RS,5RS,6SR,7RS,8SR-2,6-dimethyl-8-hydroxy-6-hydroxymethyltricyclo<5.3.11.5>undec-9-ene (88555-75-3) → (+/-)8S,14-cedranediol (18319-33-0,20315-41-7,62600-04-8,62600-05-9,88588-48-1,97723-96-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 79 percent / MnO₂ / diethyl ether / 48 h

2: p-toluenesulfonic acid / CH₂Cl₂ / 1 h / Ambient temperature

3: ethanol / 1 h / Ambient temperature

4: H₂ / Pd-C / ethanol / 20 h / Ambient temperature

5: p-toluenesulfonic acid / ethanol / 1 h

With manganese(IV) oxide; hydrogen; toluene-4-sulfonic acid; palladium on activated charcoal; In diethyl ether; ethanol; dichloromethane;

DOI:10.1016/S0040-4020(01)82444-3

Reference yield:

1SR,2RS,5RS,6SR,7RS-2,6-dimethyl-6-hydroxymethyltricyclo<5.3.1.01.5>undec-9-en-8-one (88555-76-4) → (+/-)8S,14-cedranediol (18319-33-0,20315-41-7,62600-04-8,62600-05-9,88588-48-1,97723-96-1)

Guidance literature:

Multi-step reaction with 4 steps

1: p-toluenesulfonic acid / CH₂Cl₂ / 1 h / Ambient temperature

2: ethanol / 1 h / Ambient temperature

3: H₂ / Pd-C / ethanol / 20 h / Ambient temperature

4: p-toluenesulfonic acid / ethanol / 1 h

With hydrogen; toluene-4-sulfonic acid; palladium on activated charcoal; In ethanol; dichloromethane;

DOI:10.1016/S0040-4020(01)82444-3

upstream raw materials:

methyllithium

1SR,4SR,7SR,8RS,11RS,12RS-1,8-dimethyl-4-hydroxy-3-oxatetracyclo<5.4.2^4.120^7.11>tridecane

glutaric anhydride,

1SR,2RS,5RS,6SR,7RS,8SR-2,6-dimethyl-8-hydroxy-6-hydroxymethyltricyclo<5.3.1^1.5>undec-9-ene