2-[(1R,5R)-5-Benzoyloxy-1-methyl-6-(toluene-4-sulfonyloxy)-hexyl]-malonic acid dimethyl ester

Base Information

• Chemical Name: 2-[(1R,5R)-5-Benzoyloxy-1-methyl-6-(toluene-4-sulfonyloxy)-hexyl]-malonic acid dimethyl ester
• CAS No.: 77539-29-8
• Molecular Formula: C₂₆H₃₂O₉S
• Molecular Weight: 520.601
• Mol file: 77539-29-8.mol

Synonyms:2-[(1R,5R)-5-Benzoyloxy-1-methyl-6-(toluene-4-sulfonyloxy)-hexyl]-malonic acid dimethyl ester

Chemical Property of 2-[(1R,5R)-5-Benzoyloxy-1-methyl-6-(toluene-4-sulfonyloxy)-hexyl]-malonic acid dimethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-[(1R,5R)-5-Benzoyloxy-1-methyl-6-(toluene-4-sulfonyloxy)-hexyl]-malonic acid dimethyl ester

There total 10 articles about 2-[(1R,5R)-5-Benzoyloxy-1-methyl-6-(toluene-4-sulfonyloxy)-hexyl]-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: 90.0%

2-((1R,5R)-5-Benzoyloxy-6-hydroxy-1-methyl-hexyl)-malonic acid dimethyl ester (77523-36-5) + p-toluenesulfonyl chloride (98-59-9) → 2-[(1R,5R)-5-Benzoyloxy-1-methyl-6-(toluene-4-sulfonyloxy)-hexyl]-malonic acid dimethyl ester (77539-29-8)

Guidance literature:

With pyridine;

DOI:10.1021/ja00397a059

Reference yield:

(3aR,5R,6aR)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole-5-carbaldehyde (14260-67-4) → 2-[(1R,5R)-5-Benzoyloxy-1-methyl-6-(toluene-4-sulfonyloxy)-hexyl]-malonic acid dimethyl ester (77539-29-8)

Guidance literature:

Multi-step reaction with 7 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

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

DOI:10.1021/ja00397a059

Reference yield:

D-glucose (50-99-7) → 2-[(1R,5R)-5-Benzoyloxy-1-methyl-6-(toluene-4-sulfonyloxy)-hexyl]-malonic acid dimethyl ester (77539-29-8)

Guidance literature:

Multi-step reaction with 10 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

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

DOI:10.1021/ja00397a059

upstream raw materials:

2-((1R,5R)-5-Benzoyloxy-6-hydroxy-1-methyl-hexyl)-malonic acid dimethyl ester

p-toluenesulfonyl chloride

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

D-glucose

Downstream raw materials:

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