21-benzoxy-(2R,6R,10R,14S,18S)-2,6,10,14,18-pentamethyl-1-heneicosanol

Base Information

• Chemical Name: 21-benzoxy-(2R,6R,10R,14S,18S)-2,6,10,14,18-pentamethyl-1-heneicosanol
• CAS No.: 1443233-34-8
• Molecular Formula: C₃₃H₆₀O₂
• Molecular Weight: 488.838
• Mol file: 1443233-34-8.mol

Synonyms:21-benzoxy-(2R,6R,10R,14S,18S)-2,6,10,14,18-pentamethyl-1-heneicosanol

Chemical Property of 21-benzoxy-(2R,6R,10R,14S,18S)-2,6,10,14,18-pentamethyl-1-heneicosanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 21-benzoxy-(2R,6R,10R,14S,18S)-2,6,10,14,18-pentamethyl-1-heneicosanol

There total 19 articles about 21-benzoxy-(2R,6R,10R,14S,18S)-2,6,10,14,18-pentamethyl-1-heneicosanol 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: 81.0%

21-benzoxy-1-(tert-butyldiphenylsilyloxy)-(2R,6R,10R,14S,18S)-2,6,10,14,18-pentamethylheneicosane (1443233-33-7) → 21-benzoxy-(2R,6R,10R,14S,18S)-2,6,10,14,18-pentamethyl-1-heneicosanol (1443233-34-8)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃;

DOI:10.1021/jo4006602

Reference yield:

(R)-4-((tert-Butyldiphenylsilyl)oxy)-3-methylbutanal (186641-79-2) → 21-benzoxy-(2R,6R,10R,14S,18S)-2,6,10,14,18-pentamethyl-1-heneicosanol (1443233-34-8)

Guidance literature:

Multi-step reaction with 13 steps

1.1: lithium hexamethyldisilazane / tetrahydrofuran / -78 - 20 °C / Inert atmosphere

2.1: tetrahydrofuran / 20 °C / Inert atmosphere

3.1: sodium peroxoborate tetrahydrate / tetrahydrofuran; water / 2 h / 20 °C / Inert atmosphere

4.1: sodium hydride / tetrahydrofuran / 0.17 h / 0 °C / Inert atmosphere

4.2: 20 °C / Inert atmosphere

5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 20 °C

6.1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 1 h / 0 - 20 °C / Inert atmosphere

7.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0 - 20 °C

8.1: lithium hexamethyldisilazane / tetrahydrofuran / -78 - 20 °C / Inert atmosphere

9.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 20 °C

10.1: Dess-Martin periodane / dichloromethane / 3 h / 0 - 20 °C / Inert atmosphere

11.1: lithium hexamethyldisilazane / tetrahydrofuran / -78 - 20 °C / Inert atmosphere

12.1: hydrazine; copper(II) sulfate; oxygen / ethanol / 15 h / 70 °C

13.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 20 °C

With sodium peroxoborate tetrahydrate; tetrabutyl ammonium fluoride; oxygen; sodium hydride; Dess-Martin periodane; copper(II) sulfate; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; lithium hexamethyldisilazane; hydrazine; diethylazodicarboxylate; In tetrahydrofuran; ethanol; dichloromethane; water; 1.1: |Julia-Kocienski Olefination / 8.1: |Julia-Kocienski Olefination / 11.1: |Julia-Kocienski Olefination;

DOI:10.1021/jo4006602

Reference yield:

8-benzyloxy-1-(tert-butyldiphenylsilyloxy)-(2R,6S)-2,6-dimethyloctane (1443233-14-4) → 21-benzoxy-(2R,6R,10R,14S,18S)-2,6,10,14,18-pentamethyl-1-heneicosanol (1443233-34-8)

Guidance literature:

Multi-step reaction with 10 steps

1: hydrogen; palladium 10% on activated carbon / ethyl acetate / 20 °C

2: Dess-Martin periodane / dichloromethane / 3 h / 0 °C / Inert atmosphere

3: lithium hexamethyldisilazane / tetrahydrofuran / -78 - 20 °C / Inert atmosphere

4: tetrabutyl ammonium fluoride / tetrahydrofuran / 20 °C

5: hydrazine; copper(II) sulfate; oxygen / ethanol / 15 h / 70 °C

6: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 0.5 h / 0 - 20 °C / Inert atmosphere

7: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0 - 20 °C

8: lithium hexamethyldisilazane / tetrahydrofuran / -78 - 20 °C / Inert atmosphere

9: hydrazine; copper(II) sulfate; oxygen / ethanol / 15 h / 70 °C

10: tetrabutyl ammonium fluoride / tetrahydrofuran / 20 °C

With palladium 10% on activated carbon; tetrabutyl ammonium fluoride; hydrogen; oxygen; Dess-Martin periodane; copper(II) sulfate; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; lithium hexamethyldisilazane; hydrazine; diethylazodicarboxylate; In tetrahydrofuran; ethanol; dichloromethane; ethyl acetate; 3: |Julia-Kocienski Olefination / 8: |Julia-Kocienski Olefination;

DOI:10.1021/jo4006602

upstream raw materials:

(2R)-1-(tert-butyldiphenylsilyloxy)-3-cyano-2-methylpropane

(R)-4-((tert-Butyldiphenylsilyl)oxy)-3-methylbutanal

[(2R)-5-(benzyloxy)-2-methylpentyl]oxy(tert-butyl)diphenylsilane

(2R)-5-(benzyloxy)-2-methylpentan-1-ol

Downstream raw materials:

1-benzoxy-(4S,8S,12S,16S,20S)-4,8,12,16,20-pentamethylheptacosane

1-benzoxy-(4S,8S,12S,16S,20S)-4,8,12,16,20-pentamethylpentacosane

21-benzoxy-(2R,6R,10R,14S,18S)-2,6,10,14,18-pentamethylheneicosyl p-toluenesulfonate