2-[(1R,5S)-1,9-Dimethyl-5-(toluene-4-sulfonyloxy)-decyl]-malonic acid dimethyl ester

Base Information

Chemical Name:2-[(1R,5S)-1,9-Dimethyl-5-(toluene-4-sulfonyloxy)-decyl]-malonic acid dimethyl ester
CAS No.:77523-39-8
Molecular Formula:C₂₄H₃₈O₇S
Molecular Weight:470.628
Hs Code.:

Synonyms:2-[(1R,5S)-1,9-Dimethyl-5-(toluene-4-sulfonyloxy)-decyl]-malonic acid dimethyl ester

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Chemical Property of 2-[(1R,5S)-1,9-Dimethyl-5-(toluene-4-sulfonyloxy)-decyl]-malonic acid dimethyl ester

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Technology Process of 2-[(1R,5S)-1,9-Dimethyl-5-(toluene-4-sulfonyloxy)-decyl]-malonic acid dimethyl ester

There total 12 articles about 2-[(1R,5S)-1,9-Dimethyl-5-(toluene-4-sulfonyloxy)-decyl]-malonic acid dimethyl ester 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: 75.0%

: 77523-38-7
2-((1R,5S)-5-Hydroxy-1,9-dimethyl-decyl)-malonic acid dimethyl ester

: 98-59-9
p-toluenesulfonyl chloride

: 77523-39-8
2-[(1R,5S)-1,9-Dimethyl-5-(toluene-4-sulfonyloxy)-decyl]-malonic acid dimethyl ester

Guidance literature:: With pyridine;
DOI:10.1021/ja00397a059

Reference yield:

: 14260-67-4
(3aR,5R,6aR)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole-5-carbaldehyde

: 77523-39-8
2-[(1R,5S)-1,9-Dimethyl-5-(toluene-4-sulfonyloxy)-decyl]-malonic acid dimethyl ester

Guidance literature:: Multi-step reaction with 10 steps

1: 69 percent / KO-t-Bu / tetrahydrofuran

2: 1.) PTSA, 2.) Ag₂CO₃/celite / 1.) CH₃CN, H₂O, 2.) benzene

3: 95 percent / pyridine / CH₂Cl₂

4: 95 percent / 5percentPd(PPh₃)4 / tetrahydrofuran

5: 91 percent / hydrogen / PtO₂ / ethyl acetate / 760 Torr

6: 93 percent / BH₃*S(CH₃)2 / diethyl ether

7: 90 percent / pyridine

8: 60 percent / NaOMe / methanol

9: 64 percent / diethyl ether / -10 °C

10: 75 percent / pyridine

With pyridine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; dimethylsulfide borane complex; Celite; potassium tert-butylate; hydrogen; sodium methylate; toluene-4-sulfonic acid; silver carbonate; platinum(IV) oxide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; ethyl acetate;
DOI:10.1021/ja00397a059

Reference yield:

: 50-99-7
D-glucose

: 77523-39-8
2-[(1R,5S)-1,9-Dimethyl-5-(toluene-4-sulfonyloxy)-decyl]-malonic acid dimethyl ester

Guidance literature:: Multi-step reaction with 13 steps

1: ZnCl₂, H₃PO₄ / 72 h / Ambient temperature

2: 82 percent / pyridine

4: 69 percent / KO-t-Bu / tetrahydrofuran

5: 1.) PTSA, 2.) Ag₂CO₃/celite / 1.) CH₃CN, H₂O, 2.) benzene

6: 95 percent / pyridine / CH₂Cl₂

7: 95 percent / 5percentPd(PPh₃)4 / tetrahydrofuran

8: 91 percent / hydrogen / PtO₂ / ethyl acetate / 760 Torr

9: 93 percent / BH₃*S(CH₃)2 / diethyl ether

10: 90 percent / pyridine

11: 60 percent / NaOMe / methanol

12: 64 percent / diethyl ether / -10 °C

13: 75 percent / pyridine

With pyridine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; dimethylsulfide borane complex; phosphoric acid; Celite; potassium tert-butylate; hydrogen; sodium methylate; toluene-4-sulfonic acid; silver carbonate; zinc(II) chloride; platinum(IV) oxide; In tetrahydrofuran; pyridine; methanol; diethyl ether; dichloromethane; ethyl acetate;
DOI:10.1021/ja00397a059