(S)-1-((R)-2,2-diethyl-1,3-dioxolan-4-yl)prop-2-ynyl 4-methylbenzenesulfonate

Base Information

• Chemical Name: (S)-1-((R)-2,2-diethyl-1,3-dioxolan-4-yl)prop-2-ynyl 4-methylbenzenesulfonate
• CAS No.: 1612767-74-4
• Molecular Formula: C₁₇H₂₂O₅S
• Molecular Weight: 338.425
• Mol file: 1612767-74-4.mol

Synonyms:(S)-1-((R)-2,2-diethyl-1,3-dioxolan-4-yl)prop-2-ynyl 4-methylbenzenesulfonate

Chemical Property of (S)-1-((R)-2,2-diethyl-1,3-dioxolan-4-yl)prop-2-ynyl 4-methylbenzenesulfonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-1-((R)-2,2-diethyl-1,3-dioxolan-4-yl)prop-2-ynyl 4-methylbenzenesulfonate

There total 2 articles about (S)-1-((R)-2,2-diethyl-1,3-dioxolan-4-yl)prop-2-ynyl 4-methylbenzenesulfonate 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:

(S)-1-((R)-2,2-diethyl-1,3-dioxolan-4-yl)prop-2-yn-1-ol (1612767-72-2) + p-toluenesulfonyl chloride (98-59-9) → (S)-1-((R)-2,2-diethyl-1,3-dioxolan-4-yl)prop-2-ynyl 4-methylbenzenesulfonate (1612767-74-4)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 20 ℃; for 2h; Inert atmosphere; Schlenk technique;

DOI:10.1016/j.tet.2014.03.084

Reference yield:

(R)-2,2-diethyl-1,3-dioxolane-4-carboxaldehyde (120157-60-0) → (S)-1-((R)-2,2-diethyl-1,3-dioxolan-4-yl)prop-2-ynyl 4-methylbenzenesulfonate (1612767-74-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: n-butyllithium / diethyl ether; hexane / 0.67 h / -78 - 0 °C / Inert atmosphere; Schlenk technique

1.2: 0.5 h / -78 °C / Inert atmosphere; Schlenk technique

2.1: dmap; triethylamine / dichloromethane / 2 h / 20 °C / Inert atmosphere; Schlenk technique

With dmap; n-butyllithium; triethylamine; In diethyl ether; hexane; dichloromethane;

DOI:10.1016/j.tet.2014.03.084

Reference yield:

(S)-1-((R)-2,2-diethyl-1,3-dioxolan-4-yl)prop-2-ynyl 4-methylbenzenesulfonate (1612767-74-4) → C29H50N2O8SeSi

Guidance literature:

Multi-step reaction with 10 steps

1.1: diisopropylamine; n-butyllithium / hexane; tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere; Schlenk technique

1.2: 1.25 h / -78 °C / Inert atmosphere; Schlenk technique

1.3: 0.37 h / -78 °C / Inert atmosphere; Schlenk technique

2.1: lithium aluminium tetrahydride / tetrahydrofuran / 0.33 h / 0 °C / Inert atmosphere; Schlenk technique

3.1: pyridine; sulphamoyl chloride / dichloromethane / 0.83 h / 0 - 20 °C / Inert atmosphere; Schlenk technique

4.1: dirhodium tetraacetate / dichloromethane / 0.08 h / 20 °C / Inert atmosphere; Schlenk technique

4.2: 2 h / 20 °C / Inert atmosphere; Schlenk technique

5.1: water / acetonitrile / 2 h / 20 °C

6.1: 2,6-dimethylpyridine / dichloromethane / 0.5 h / Inert atmosphere; Schlenk technique

7.1: 3,3-dimethyldioxirane / dichloromethane / 2 h / 0 °C / Molecular sieve

8.1: zinc(II) tetrahydroborate / dichloromethane; tetrahydrofuran / 2 h / -78 °C / Inert atmosphere; Schlenk technique

9.1: dmap; triethylamine / dichloromethane / 0.67 h / 0 °C / Inert atmosphere; Schlenk technique

10.1: sodium tetrahydroborate / ethanol / 0.33 h / Inert atmosphere; Schlenk technique

10.2: 4 h / 20 °C / Inert atmosphere; Schlenk technique

With pyridine; 2,6-dimethylpyridine; dmap; dirhodium tetraacetate; sodium tetrahydroborate; lithium aluminium tetrahydride; n-butyllithium; zinc(II) tetrahydroborate; sulphamoyl chloride; water; 3,3-dimethyldioxirane; triethylamine; diisopropylamine; In tetrahydrofuran; ethanol; hexane; dichloromethane; acetonitrile;

DOI:10.1016/j.tet.2014.03.084

upstream raw materials:

(S)-1-((R)-2,2-diethyl-1,3-dioxolan-4-yl)prop-2-yn-1-ol

p-toluenesulfonyl chloride

(R)-2,2-diethyl-1,3-dioxolane-4-carboxaldehyde