(2R,3S)-3-ethyl-1,2-(4-methoxybenzylidenedioxy)-6-(4-methoxybenzyloxy)-4-hexyne

Base Information

• Chemical Name: (2R,3S)-3-ethyl-1,2-(4-methoxybenzylidenedioxy)-6-(4-methoxybenzyloxy)-4-hexyne
• CAS No.: 943144-57-8
• Molecular Formula: C₂₄H₂₈O₅
• Molecular Weight: 396.483
• Mol file: 943144-57-8.mol

Synonyms:(2R,3S)-3-ethyl-1,2-(4-methoxybenzylidenedioxy)-6-(4-methoxybenzyloxy)-4-hexyne

Chemical Property of (2R,3S)-3-ethyl-1,2-(4-methoxybenzylidenedioxy)-6-(4-methoxybenzyloxy)-4-hexyne

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S)-3-ethyl-1,2-(4-methoxybenzylidenedioxy)-6-(4-methoxybenzyloxy)-4-hexyne

There total 3 articles about (2R,3S)-3-ethyl-1,2-(4-methoxybenzylidenedioxy)-6-(4-methoxybenzyloxy)-4-hexyne 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: 60.0%

(2R,3S)-3-ethyl-6-(4-methoxybenzyloxy)-4-hexyne-1,2-diol (943144-56-7) + p-Anisaldehyde dimethyl acetal (2186-92-7) → (2R,3S)-3-ethyl-1,2-(4-methoxybenzylidenedioxy)-6-(4-methoxybenzyloxy)-4-hexyne (943144-57-8)

Guidance literature:

With pyridinium p-toluenesulfonate; In dichloromethane; at 20 ℃; for 2h;

DOI:10.1016/j.tetlet.2007.03.152

Reference yield:

(E)-2-penten-1-ol (1576-96-1) → (2R,3S)-3-ethyl-1,2-(4-methoxybenzylidenedioxy)-6-(4-methoxybenzyloxy)-4-hexyne (943144-57-8)

Guidance literature:

Multi-step reaction with 3 steps

1: L-(+)-DIPT; TBHP; MS 4 Angstroem / Ti(Oi-Pr)4 / CH₂Cl₂ / -20 °C

2: 39 percent / n-BuLi; Et₂AlCl / toluene / 44 h / -20 - 20 °C

3: 60 percent / PPTS / CH₂Cl₂ / 2 h / 20 °C

With tert.-butylhydroperoxide; n-butyllithium; L-(+)-diisopropyl tartrate; MS 4 Angstroem; diethylaluminium chloride; pyridinium p-toluenesulfonate; titanium(IV) isopropylate; In dichloromethane; toluene; 1: Sharpless asymmetric epoxidation;

DOI:10.1016/j.tetlet.2007.03.152

Reference yield:

((2S,3S)-3-ethyloxiran-2-yl)methanol (104530-72-5) → (2R,3S)-3-ethyl-1,2-(4-methoxybenzylidenedioxy)-6-(4-methoxybenzyloxy)-4-hexyne (943144-57-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 39 percent / n-BuLi; Et₂AlCl / toluene / 44 h / -20 - 20 °C

2: 60 percent / PPTS / CH₂Cl₂ / 2 h / 20 °C

With n-butyllithium; diethylaluminium chloride; pyridinium p-toluenesulfonate; In dichloromethane; toluene;

DOI:10.1016/j.tetlet.2007.03.152

upstream raw materials:

(2R,3S)-3-ethyl-6-(4-methoxybenzyloxy)-4-hexyne-1,2-diol

p-Anisaldehyde dimethyl acetal

(E)-2-penten-1-ol

((2S,3S)-3-ethyloxiran-2-yl)methanol

Downstream raw materials:

C₂₄H₃₀O₅

(2R,3S,4Z)-3-ethyl-2,6-bis(4-methoxybenzyloxy)-4-hexen-1-ol

(2R,3S,4Z)-1-(benzothiazole-2-thio)-3-ethyl-2,6-bis(4-methoxybenzyloxy)-4-hexen-1-ol

(2R,3S,4Z)-1-(benzothiazole-2-sulfonyl)-3-ethyl-2,6-bis(4-methoxybenzyloxy)-4-hexene