(7R,8R)-(+)-8-hydroxy-7-p-toluenesulfonyloxy-2-methyloctadecane

Base Information

• Chemical Name: (7R,8R)-(+)-8-hydroxy-7-p-toluenesulfonyloxy-2-methyloctadecane
• CAS No.: 105243-14-9
• Molecular Formula: C₂₆H₄₆O₄S
• Molecular Weight: 454.715
• Mol file: 105243-14-9.mol

Synonyms:(7R,8R)-(+)-8-hydroxy-7-p-toluenesulfonyloxy-2-methyloctadecane

Chemical Property of (7R,8R)-(+)-8-hydroxy-7-p-toluenesulfonyloxy-2-methyloctadecane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (7R,8R)-(+)-8-hydroxy-7-p-toluenesulfonyloxy-2-methyloctadecane

There total 18 articles about (7R,8R)-(+)-8-hydroxy-7-p-toluenesulfonyloxy-2-methyloctadecane 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: 92.0%

(7R,8R)-8-benzyloxy-7-p-toluenesulfonyloxy-2-methyl-9-octadecane (120665-38-5) → (7R,8R)-(+)-8-hydroxy-7-p-toluenesulfonyloxy-2-methyloctadecane (105243-14-9)

Guidance literature:

With hydrogen; palladium on activated charcoal; In acetic acid; for 2h; under 760 Torr; Ambient temperature;

Reference yield:

C41H66O4 → (7R,8R)-(+)-8-hydroxy-7-p-toluenesulfonyloxy-2-methyloctadecane (105243-14-9)

Guidance literature:

Multi-step reaction with 6 steps

1: 0.47 g / iron(III) chloride hexahydrate / CH₂Cl₂ / 2.5 h / 20 °C

2: lead(IV) acetate / benzene / 1.5 h / 20 °C

3: 0.18 g / magnesium bromide diethyl etherate / CH₂Cl₂ / 2 h / -78 °C

4: 87 percent / 4-dimethylaminopyridine / CH₂Cl₂ / 5 h / 20 °C

5: 92 percent / Grubbs catalyst 2nd generation / CH₂Cl₂ / 6 h / Heating

6: 90 percent / hydrogen / palladium on carbon / methanol / 3 h / 20 °C

With lead(IV) acetate; dmap; hydrogen; iron(III) chloride; magnesium bromide ethyl etherate; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; palladium on activated charcoal; In methanol; dichloromethane; benzene; 3: Keck allylation;

DOI:10.1021/jo070060o

Reference yield:

(4R,5R)-4,5-diundecanoyl-2,2-dimethyl-1,3-dioxolane (936650-18-9) → (7R,8R)-(+)-8-hydroxy-7-p-toluenesulfonyloxy-2-methyloctadecane (105243-14-9)

Guidance literature:

Multi-step reaction with 8 steps

1: 93 percent / K-Selectride / tetrahydrofuran / 2.5 h / -78 °C

2: sodium hydride / dimethylformamide / 2 h / 0 °C

3: 0.47 g / iron(III) chloride hexahydrate / CH₂Cl₂ / 2.5 h / 20 °C

4: lead(IV) acetate / benzene / 1.5 h / 20 °C

5: 0.18 g / magnesium bromide diethyl etherate / CH₂Cl₂ / 2 h / -78 °C

6: 87 percent / 4-dimethylaminopyridine / CH₂Cl₂ / 5 h / 20 °C

7: 92 percent / Grubbs catalyst 2nd generation / CH₂Cl₂ / 6 h / Heating

8: 90 percent / hydrogen / palladium on carbon / methanol / 3 h / 20 °C

With lead(IV) acetate; dmap; hydrogen; iron(III) chloride; sodium hydride; potassium tri-sec-butyl-borohydride; magnesium bromide ethyl etherate; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; benzene; 5: Keck allylation;

DOI:10.1021/jo070060o

upstream raw materials:

(7R,8R)-8-benzyloxy-7-p-toluenesulfonyloxy-2-methyl-9-octadecane

(4R,5R)-5-(benzyloxy)pentadec-1-en-4-ol

(4R,5R)-5-(benzyloxy)-4-(p-toluenesulfonyloxy)pentadec-1-ene

(4R,5R)-4,5-diundecanoyl-2,2-dimethyl-1,3-dioxolane