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

Base Information

Chemical Name:21-benzoxy-(2R,6R,10R,14S,18S)-2,6,10,14,18-pentamethylheneicosyl p-toluenesulfonate
CAS No.:1443233-35-9
Molecular Formula:C₄₀H₆₆O₄S
Molecular Weight:643.028
Hs Code.:

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

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

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

There total 21 articles about 21-benzoxy-(2R,6R,10R,14S,18S)-2,6,10,14,18-pentamethylheneicosyl p-toluenesulfonate 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: 78.0%

: 1443233-34-8
21-benzoxy-(2R,6R,10R,14S,18S)-2,6,10,14,18-pentamethyl-1-heneicosanol

: 98-59-9
p-toluenesulfonyl chloride

: 1443233-35-9
21-benzoxy-(2R,6R,10R,14S,18S)-2,6,10,14,18-pentamethylheneicosyl p-toluenesulfonate

Guidance literature:: With dmap; In pyridine; at 0 - 20 ℃; Inert atmosphere;
DOI:10.1021/jo4006602

Reference yield:

: 186641-79-2
(R)-4-((tert-Butyldiphenylsilyl)oxy)-3-methylbutanal

: 1443233-35-9
21-benzoxy-(2R,6R,10R,14S,18S)-2,6,10,14,18-pentamethylheneicosyl p-toluenesulfonate

Guidance literature:: Multi-step reaction with 14 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

14.1: dmap / pyridine / 0 - 20 °C / Inert atmosphere

With dmap; 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; pyridine; ethanol; dichloromethane; water; 1.1: |Julia-Kocienski Olefination / 8.1: |Julia-Kocienski Olefination / 11.1: |Julia-Kocienski Olefination;
DOI:10.1021/jo4006602

Reference yield:

: 1443233-14-4
8-benzyloxy-1-(tert-butyldiphenylsilyloxy)-(2R,6S)-2,6-dimethyloctane

: 1443233-35-9
21-benzoxy-(2R,6R,10R,14S,18S)-2,6,10,14,18-pentamethylheneicosyl p-toluenesulfonate

Guidance literature:: Multi-step reaction with 11 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

11: dmap / pyridine / 0 - 20 °C / Inert atmosphere

With dmap; 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; pyridine; ethanol; dichloromethane; ethyl acetate; 3: |Julia-Kocienski Olefination / 8: |Julia-Kocienski Olefination;
DOI:10.1021/jo4006602