(2S,5S)-5-ethynyl-2-[(p-toluenesulfonyloxy)methyl]tetrahydrofuran

Base Information

• Chemical Name: (2S,5S)-5-ethynyl-2-[(p-toluenesulfonyloxy)methyl]tetrahydrofuran
• CAS No.: 254891-68-4
• Molecular Formula: C₁₄H₁₆O₄S
• Molecular Weight: 280.345
• Mol file: 254891-68-4.mol

Synonyms:(2S,5S)-5-ethynyl-2-[(p-toluenesulfonyloxy)methyl]tetrahydrofuran

Chemical Property of (2S,5S)-5-ethynyl-2-[(p-toluenesulfonyloxy)methyl]tetrahydrofuran

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,5S)-5-ethynyl-2-[(p-toluenesulfonyloxy)methyl]tetrahydrofuran

There total 14 articles about (2S,5S)-5-ethynyl-2-[(p-toluenesulfonyloxy)methyl]tetrahydrofuran 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: 82.0%

trimethylene mannitol + ethyl acetate n-hexane + p-toluenesulfonyl chloride (98-59-9) + (2S,5S)-5-ethynyl-2-(hydroxymethyl)tetrahydrofuran (254891-67-3) → (2S,5S)-5-ethynyl-2-[(p-toluenesulfonyloxy)methyl]tetrahydrofuran (254891-68-4)

Guidance literature:

With triethylamine; In dmap; dichloromethane;

Reference yield: 69.0%

p-toluenesulfonyl chloride (98-59-9) + (2S,5S)-5-ethynyl-2-(hydroxymethyl)tetrahydrofuran (254891-67-3) → (2S,5S)-5-ethynyl-2-[(p-toluenesulfonyloxy)methyl]tetrahydrofuran (254891-68-4)

Guidance literature:

With triethylamine; In dichloromethane; at 20 ℃; for 8h;

DOI:10.1016/j.tetasy.2005.01.044

Reference yield:

(R)-3-(2,2-dimethyl-1,3-dioxolan-4-yl)propanal (133008-09-0) → (2S,5S)-5-ethynyl-2-[(p-toluenesulfonyloxy)methyl]tetrahydrofuran (254891-68-4)

Guidance literature:

Multi-step reaction with 10 steps

1: 65 percent / benzene / 6 h / Heating

2: 98 percent / DIBAL-H / CH₂Cl₂; hexane / 2 h / -20 °C

3: 72 percent / (+)-DIPT; cumene hydroperoxide; molecular sieves 4 Angstroem / Ti(OiPr)4 / CH₂Cl₂ / 3 h / -20 °C

4: 75 percent / Ph₃P; NaHCO₃; CCl₄ / 3 h / Heating

5: 83 percent / LDA / tetrahydrofuran; hexane / 3 h / -40 °C

6: 91 percent / Et₃N / CH₂Cl₂ / 0.5 h / 0 - 20 °C

7: 66 percent / acetic acid / H₂O / 12 h / 20 °C

8: 89 percent / Et₃N / CH₂Cl₂ / 8 h / 20 °C

9: 95 percent / K₂CO₃ / methanol / 2 h / 20 °C

10: 69 percent / Et₃N / CH₂Cl₂ / 8 h / 20 °C

With tetrachloromethane; L-(+)-diisopropyl tartrate; Cumene hydroperoxide; 4 A molecular sieve; diisobutylaluminium hydride; sodium hydrogencarbonate; potassium carbonate; acetic acid; triethylamine; triphenylphosphine; lithium diisopropyl amide; titanium(IV) isopropylate; In tetrahydrofuran; methanol; hexane; dichloromethane; water; benzene; 1: Wittig olefination;

DOI:10.1016/j.tetasy.2005.01.044

upstream raw materials:

p-toluenesulfonyl chloride

(2S,5S)-5-ethynyl-2-(hydroxymethyl)tetrahydrofuran

(R)-3-(2,2-dimethyl-1,3-dioxolan-4-yl)propanal

ethyl (E)-3-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]acrylate

Downstream raw materials:

(2S,5S)-2-ethynyl-5-[(4-fluorophenoxy)methyl]tetrahydrofuran