N-tosyl 18-(4-methoxybenzyloxy)-methyl reserpate

Base Information

Chemical Name:N-tosyl 18-(4-methoxybenzyloxy)-methyl reserpate
CAS No.:1421052-35-8
Molecular Formula:C₃₈H₄₄N₂O₈S
Molecular Weight:688.842
Hs Code.:

Synonyms:N-tosyl 18-(4-methoxybenzyloxy)-methyl reserpate

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Chemical Property of N-tosyl 18-(4-methoxybenzyloxy)-methyl reserpate

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Technology Process of N-tosyl 18-(4-methoxybenzyloxy)-methyl reserpate

There total 14 articles about N-tosyl 18-(4-methoxybenzyloxy)-methyl reserpate 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: 44.0%

: 1421052-34-7
C₃₈H₄₂N₂O₈S

: 1421052-35-8
N-tosyl 18-(4-methoxybenzyloxy)-methyl reserpate

Guidance literature:: With decane; hydrogen; In dichloromethane; at 20 ℃; for 16h; under 760.051 Torr;
DOI:10.1021/ol400046n

Reference yield:

: 1421052-20-1
(S)-(4-(benzyloxy)-3-methoxybutoxy)(tert-butyl)dimethylsilane

: 1421052-35-8
N-tosyl 18-(4-methoxybenzyloxy)-methyl reserpate

Guidance literature:: Multi-step reaction with 14 steps

1.1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 9 h / 20 °C / Inert atmosphere

2.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -60 °C

2.2: -60 - 20 °C

3.1: titanium(IV) trichloride isopropoxide / dichloromethane / 0.33 h / -78 °C / Inert atmosphere

3.2: -78 °C / Inert atmosphere

4.1: trifluorormethanesulfonic acid / diethyl ether / 1.75 h / -20 - 20 °C

5.1: tert.-butyl lithium / diethyl ether; pentane / 0.58 h / -78 °C / Inert atmosphere

5.2: 1.5 h / -78 °C / Inert atmosphere

6.1: C₁₇H₃₄N₄OS; acetic acid / toluene / 110 h / 20 - 45 °C / Inert atmosphere

7.1: pyridine hydrogenfluoride / tetrahydrofuran / 16 h / 0 - 20 °C

8.1: Dess-Martin periodane / dichloromethane / 1 h / 20 °C

9.1: piperidine; toluene-4-sulfonic acid / toluene / Inert atmosphere

10.1: 2-methyl-but-2-ene; sodium dihydrogenphosphate; sodium chlorite / tert-butyl alcohol; water; acetone / 1.5 h

11.1: ethyl acetate; diethyl ether; ethanol

12.1: n-butyllithium / tetrahydrofuran; hexane / 0.17 h / -78 °C / Inert atmosphere

12.2: 3 h / -78 - 20 °C

13.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / 15 h / 110 °C

14.1: hydrogen; decane / dichloromethane / 16 h / 20 °C / 760.05 Torr

With piperidine; sodium chlorite; sodium dihydrogenphosphate; n-butyllithium; 2-methyl-but-2-ene; oxalyl dichloride; titanium(IV) trichloride isopropoxide; decane; trifluorormethanesulfonic acid; palladium 10% on activated carbon; C₁₇H₃₄N₄OS; hydrogen; tert.-butyl lithium; Dess-Martin periodane; toluene-4-sulfonic acid; pyridine hydrogenfluoride; acetic acid; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; diethyl ether; ethanol; hexane; dichloromethane; water; ethyl acetate; acetone; toluene; tert-butyl alcohol; pentane; 2.1: |Swern Oxidation / 2.2: |Swern Oxidation;
DOI:10.1021/ol400046n

Reference yield:

: (S)-4-(tert-butyldimethylsilyloxy)-2-methoxybutanal

: 1421052-35-8
N-tosyl 18-(4-methoxybenzyloxy)-methyl reserpate

Guidance literature:: Multi-step reaction with 12 steps

1.1: titanium(IV) trichloride isopropoxide / dichloromethane / 0.33 h / -78 °C / Inert atmosphere

1.2: -78 °C / Inert atmosphere

2.1: trifluorormethanesulfonic acid / diethyl ether / 1.75 h / -20 - 20 °C

3.1: tert.-butyl lithium / diethyl ether; pentane / 0.58 h / -78 °C / Inert atmosphere

3.2: 1.5 h / -78 °C / Inert atmosphere

4.1: C₁₇H₃₄N₄OS; acetic acid / toluene / 110 h / 20 - 45 °C / Inert atmosphere

5.1: pyridine hydrogenfluoride / tetrahydrofuran / 16 h / 0 - 20 °C

6.1: Dess-Martin periodane / dichloromethane / 1 h / 20 °C

7.1: piperidine; toluene-4-sulfonic acid / toluene / Inert atmosphere

8.1: 2-methyl-but-2-ene; sodium dihydrogenphosphate; sodium chlorite / tert-butyl alcohol; water; acetone / 1.5 h

9.1: ethyl acetate; diethyl ether; ethanol

10.1: n-butyllithium / tetrahydrofuran; hexane / 0.17 h / -78 °C / Inert atmosphere

10.2: 3 h / -78 - 20 °C

11.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / 15 h / 110 °C

12.1: hydrogen; decane / dichloromethane / 16 h / 20 °C / 760.05 Torr

With piperidine; sodium chlorite; sodium dihydrogenphosphate; n-butyllithium; 2-methyl-but-2-ene; titanium(IV) trichloride isopropoxide; decane; trifluorormethanesulfonic acid; C₁₇H₃₄N₄OS; hydrogen; tert.-butyl lithium; Dess-Martin periodane; toluene-4-sulfonic acid; pyridine hydrogenfluoride; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; diethyl ether; ethanol; hexane; dichloromethane; water; ethyl acetate; acetone; toluene; tert-butyl alcohol; pentane;
DOI:10.1021/ol400046n