1-[5-(1-ethynyl)-2,2-dimethyl-(4S,5R)-1,3-dioxolan-4-yl]-3-triphenylmethyloxy-(1S)-propan-1-ol

Base Information

• Chemical Name: 1-[5-(1-ethynyl)-2,2-dimethyl-(4S,5R)-1,3-dioxolan-4-yl]-3-triphenylmethyloxy-(1S)-propan-1-ol
• CAS No.: 385810-27-5
• Molecular Formula: C₂₉H₃₀O₄
• Molecular Weight: 442.555
• Mol file: 385810-27-5.mol

Synonyms:1-[5-(1-ethynyl)-2,2-dimethyl-(4S,5R)-1,3-dioxolan-4-yl]-3-triphenylmethyloxy-(1S)-propan-1-ol

Chemical Property of 1-[5-(1-ethynyl)-2,2-dimethyl-(4S,5R)-1,3-dioxolan-4-yl]-3-triphenylmethyloxy-(1S)-propan-1-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-[5-(1-ethynyl)-2,2-dimethyl-(4S,5R)-1,3-dioxolan-4-yl]-3-triphenylmethyloxy-(1S)-propan-1-ol

There total 4 articles about 1-[5-(1-ethynyl)-2,2-dimethyl-(4S,5R)-1,3-dioxolan-4-yl]-3-triphenylmethyloxy-(1S)-propan-1-ol 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%

trityl chloride (76-83-5) + 1-[5-(1-ethynyl)-2,2-dimethyl-(4S,5R)-1,3-dioxolan-4-yl]-(1S)-propane-1,3-diol (385810-26-4) → 1-[5-(1-ethynyl)-2,2-dimethyl-(4S,5R)-1,3-dioxolan-4-yl]-3-triphenylmethyloxy-(1S)-propan-1-ol (385810-27-5)

Guidance literature:

With triethylamine; In dichloromethane; at 20 ℃; for 1h;

DOI:10.1021/jo010455m

Reference yield:

ethyl 2-{(3aS,4S,6R,6aR)-6-(hydroxymethyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl}acetate (55797-78-9) → 1-[5-(1-ethynyl)-2,2-dimethyl-(4S,5R)-1,3-dioxolan-4-yl]-3-triphenylmethyloxy-(1S)-propan-1-ol (385810-27-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 88 percent / CCl₄; PPh₃ / 6 h / Heating

2: 90 percent / LiAlH₄ / diethyl ether / 0 - 20 °C

3: 91 percent / LiNH₂; liquid NH₃ / tetrahydrofuran / 1 h

4: 90 percent / et3N / CH₂Cl₂ / 1 h / 20 °C

With tetrachloromethane; lithium aluminium tetrahydride; lithium amide; ammonia; triethylamine; triphenylphosphine; In tetrahydrofuran; diethyl ether; dichloromethane;

DOI:10.1021/jo010455m

Reference yield:

2-[6-chloromethyl-2,2-dimethyl-(3aS,4S,6S,6aS)-perhydrofuro[3,4-d][1,3]dioxol-4-yl]-1-ethanol (385810-25-3) → 1-[5-(1-ethynyl)-2,2-dimethyl-(4S,5R)-1,3-dioxolan-4-yl]-3-triphenylmethyloxy-(1S)-propan-1-ol (385810-27-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 91 percent / LiNH₂; liquid NH₃ / tetrahydrofuran / 1 h

2: 90 percent / et3N / CH₂Cl₂ / 1 h / 20 °C

With lithium amide; ammonia; triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo010455m

upstream raw materials:

trityl chloride

1-[5-(1-ethynyl)-2,2-dimethyl-(4S,5R)-1,3-dioxolan-4-yl]-(1S)-propane-1,3-diol

ethyl 2-{(3aS,4S,6R,6aR)-6-(hydroxymethyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl}acetate

2-[6-chloromethyl-2,2-dimethyl-(3aS,4S,6S,6aS)-perhydrofuro[3,4-d][1,3]dioxol-4-yl]-1-ethanol

Downstream raw materials:

4-[1-tert-butyldimethylsilyloxy-3-triphenylmethyloxy-(1S)-propyl]-5-(1-ethynyl-2,2-dimethyl)-(4R,5R)-1,3-dioxolane