((R)-2,2-cyclohexylidine-1,3-dioxolan-4-yl)methyl 4-methylbenzenesulphonate

Base Information

• Chemical Name: ((R)-2,2-cyclohexylidine-1,3-dioxolan-4-yl)methyl 4-methylbenzenesulphonate
• CAS No.: 1638138-12-1
• Molecular Formula: C₁₆H₂₂O₅S
• Molecular Weight: 326.414
• Mol file: 1638138-12-1.mol

Synonyms:((R)-2,2-cyclohexylidine-1,3-dioxolan-4-yl)methyl 4-methylbenzenesulphonate

Chemical Property of ((R)-2,2-cyclohexylidine-1,3-dioxolan-4-yl)methyl 4-methylbenzenesulphonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ((R)-2,2-cyclohexylidine-1,3-dioxolan-4-yl)methyl 4-methylbenzenesulphonate

There total 2 articles about ((R)-2,2-cyclohexylidine-1,3-dioxolan-4-yl)methyl 4-methylbenzenesulphonate 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: 97.0%

(S)-1,4-dioxaspiro<4.5>decane-2-methanol (95335-91-4) + p-toluenesulfonyl chloride (98-59-9) → ((R)-2,2-cyclohexylidine-1,3-dioxolan-4-yl)methyl 4-methylbenzenesulphonate (1638138-12-1)

Guidance literature:

(S)-1,4-dioxaspiro<4.5>decane-2-methanol; With triethylamine; In dichloromethane; at 0 ℃; for 0.25h;

p-toluenesulfonyl chloride; In dichloromethane; at 20 ℃; for 6h;

DOI:10.1016/j.carres.2019.107892

Reference yield:

cyclohexanone (108-94-1,11119-77-0,9003-41-2,9075-99-4) → ((R)-2,2-cyclohexylidine-1,3-dioxolan-4-yl)methyl 4-methylbenzenesulphonate (1638138-12-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: orthoformic acid triethyl ester; trifluoroborane diethyl ether / dimethyl sulfoxide / 12 h / 20 °C

1.2: 6 h / 0 - 20 °C

2.1: sodium tetrahydroborate / methanol / 3 h / 0 - 20 °C

3.1: triethylamine / dichloromethane / 0.25 h / 0 °C

3.2: 6 h / 20 °C

With sodium tetrahydroborate; trifluoroborane diethyl ether; triethylamine; orthoformic acid triethyl ester; In methanol; dichloromethane; dimethyl sulfoxide;

DOI:10.1016/j.carres.2019.107892

Reference yield: 85.0%

((R)-2,2-cyclohexylidine-1,3-dioxolan-4-yl)methyl 4-methylbenzenesulphonate (1638138-12-1) → (R)-3-tosyloxy-1,2-propanediol (41274-09-3)

Guidance literature:

With toluene-4-sulfonic acid; In methanol; at 20 ℃; for 24h;

DOI:10.1016/j.carres.2019.107892

upstream raw materials:

(S)-1,4-dioxaspiro<4.5>decane-2-methanol

p-toluenesulfonyl chloride

cyclohexanone

Downstream raw materials:

(R)-3-tosyloxy-1,2-propanediol

Refernces

• 1、 Saha,Chakraborty,Roy. "A concise and simple synthesis of 1-hydroxy-phenethylamine derivatives: Formal synthesis of naturally occurring norephedrine, virolin and 3-hydroxy-2-phosphonylmethoxypropyl adenine". . p. 837 - 846. Retrieved 2014/07/07.