21-benzoxy-1-(tert-butyldiphenylsilyloxy)-(2R,6R,10R,14S,18S)-2,6,10,14,18-pentamethylheneicosane

Base Information

• Chemical Name: 21-benzoxy-1-(tert-butyldiphenylsilyloxy)-(2R,6R,10R,14S,18S)-2,6,10,14,18-pentamethylheneicosane
• CAS No.: 1443233-33-7
• Molecular Formula: C₄₉H₇₈O₂Si
• Molecular Weight: 727.243
• Mol file: 1443233-33-7.mol

Synonyms:21-benzoxy-1-(tert-butyldiphenylsilyloxy)-(2R,6R,10R,14S,18S)-2,6,10,14,18-pentamethylheneicosane

Chemical Property of 21-benzoxy-1-(tert-butyldiphenylsilyloxy)-(2R,6R,10R,14S,18S)-2,6,10,14,18-pentamethylheneicosane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 21-benzoxy-1-(tert-butyldiphenylsilyloxy)-(2R,6R,10R,14S,18S)-2,6,10,14,18-pentamethylheneicosane

There total 18 articles about 21-benzoxy-1-(tert-butyldiphenylsilyloxy)-(2R,6R,10R,14S,18S)-2,6,10,14,18-pentamethylheneicosane 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: 96.0%

1-benzoxy-21-(tert-butyldiphenylsilyloxy)-(4R,8S,12R,16S,20S)-4,8,12,16,20-pentamethyl-5-(E/Z)-13-(E/Z)-heneicosa-5,13-diene (1443233-28-0) → 21-benzoxy-1-(tert-butyldiphenylsilyloxy)-(2R,6R,10R,14S,18S)-2,6,10,14,18-pentamethylheneicosane (1443233-33-7)

Guidance literature:

With oxygen; copper(II) sulfate; hydrazine; In ethanol; at 70 ℃; for 15h;

DOI:10.1021/jo4006602

Reference yield: 78.0%

21-benzoxy-1-(tert-butyldiphenylsilyloxy)-(2R,6S,10R,14R,18S)-2,6,10,14,18-pentamethyl-8-(E/Z)-8-heneicosene → 21-benzoxy-1-(tert-butyldiphenylsilyloxy)-(2R,6R,10R,14S,18S)-2,6,10,14,18-pentamethylheneicosane (1443233-33-7)

Guidance literature:

With oxygen; copper(II) sulfate; hydrazine; In ethanol; at 70 ℃; for 15h;

DOI:10.1021/jo4006602

Reference yield:

(2R)-1-(tert-butyldiphenylsilyloxy)-3-cyano-2-methylpropane (186641-76-9) → 21-benzoxy-1-(tert-butyldiphenylsilyloxy)-(2R,6R,10R,14S,18S)-2,6,10,14,18-pentamethylheneicosane (1443233-33-7)

Guidance literature:

Multi-step reaction with 13 steps

1.1: diisobutylaluminium hydride

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

3.1: tetrahydrofuran / 20 °C / Inert atmosphere

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

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

5.2: 20 °C / Inert atmosphere

6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 20 °C

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

8.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0 - 20 °C

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

10.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 20 °C

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

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

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

With sodium peroxoborate tetrahydrate; tetrabutyl ammonium fluoride; oxygen; sodium hydride; diisobutylaluminium hydride; Dess-Martin periodane; copper(II) sulfate; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; lithium hexamethyldisilazane; hydrazine; diethylazodicarboxylate; In tetrahydrofuran; ethanol; dichloromethane; water; 2.1: |Julia-Kocienski Olefination / 9.1: |Julia-Kocienski Olefination / 12.1: |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

(4R)-5-[1-(tert-butyl)-1,1-diphenylsilyl]oxy-4-methylpentan-1-ol

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

Downstream raw materials:

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

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

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