(4S,2'S,4'S)-acetic acid 4-methoxymethoxy-4-(2'-phenyl-[1,3]dioxan-4'-yl)but-2-ynyl ester

Base Information

• Chemical Name: (4S,2'S,4'S)-acetic acid 4-methoxymethoxy-4-(2'-phenyl-[1,3]dioxan-4'-yl)but-2-ynyl ester
• CAS No.: 760210-80-8
• Molecular Formula: C₁₈H₂₂O₆
• Molecular Weight: 334.369
• Mol file: 760210-80-8.mol

Synonyms:(4S,2'S,4'S)-acetic acid 4-methoxymethoxy-4-(2'-phenyl-[1,3]dioxan-4'-yl)but-2-ynyl ester

Chemical Property of (4S,2'S,4'S)-acetic acid 4-methoxymethoxy-4-(2'-phenyl-[1,3]dioxan-4'-yl)but-2-ynyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S,2'S,4'S)-acetic acid 4-methoxymethoxy-4-(2'-phenyl-[1,3]dioxan-4'-yl)but-2-ynyl ester

There total 2 articles about (4S,2'S,4'S)-acetic acid 4-methoxymethoxy-4-(2'-phenyl-[1,3]dioxan-4'-yl)but-2-ynyl ester 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:

chloromethyl methyl ether (107-30-2) + (4S,2'S,4'S)-acetic acid 4-hydroxy-4-(2'-phenyl-[1,3]dioxan-4'-yl)but-2-ynyl ester (760210-79-5) → (4S,2'S,4'S)-acetic acid 4-methoxymethoxy-4-(2'-phenyl-[1,3]dioxan-4'-yl)but-2-ynyl ester (760210-80-8)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃;

DOI:10.1021/ja047190o

Reference yield:

Propargyl acetate (627-09-8) → (4S,2'S,4'S)-acetic acid 4-methoxymethoxy-4-(2'-phenyl-[1,3]dioxan-4'-yl)but-2-ynyl ester (760210-80-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 89 percent / Zn(OTf)2; (+)-N-methylephedrine; Et₃N / toluene / 1.5 h / 20 °C

2: i-Pr₂NEt / CH₂Cl₂ / 20 °C

With zinc trifluoromethanesulfonate; (+)-N-methylephedrine; triethylamine; N-ethyl-N,N-diisopropylamine; In dichloromethane; toluene;

DOI:10.1021/ja047190o

Reference yield:

(4S,2'S,4'S)-acetic acid 4-methoxymethoxy-4-(2'-phenyl-[1,3]dioxan-4'-yl)but-2-ynyl ester (760210-80-8) → (Z)-(1S,2S,4S)-4-(5,5-dibromo-1-methoxymethoxy-penta-2,4-dienyl)-2-phenyl[1,3]dioxane (760210-83-1)

Guidance literature:

Multi-step reaction with 4 steps

1: K₂CO₃; methanol / 0.5 h / 0 °C

2: 1.42 g / H₂; quinoline / Lindlar's catalyst / methanol / 24 h / 20 °C

3: IBX; DMSO / 1 h / 20 °C

4: 1.10 g / PPh₃; Et₃N / CH₂Cl₂ / 0.75 h / 0 °C

With quinoline; methanol; hydrogen; potassium carbonate; dimethyl sulfoxide; triethylamine; triphenylphosphine; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; Lindlar's catalyst; In methanol; dichloromethane;

DOI:10.1021/ja047190o

upstream raw materials:

chloromethyl methyl ether

(4S,2'S,4'S)-acetic acid 4-hydroxy-4-(2'-phenyl-[1,3]dioxan-4'-yl)but-2-ynyl ester

Propargyl acetate

Downstream raw materials:

(4S,2'S,4'S)-4-methoxymethoxy-4-(2'-phenyl-[1,3]dioxan-4'-yl)but-2-yn-1-ol

(Z)-(4S,2'S,4'S)-4-methoxymethoxy-4-(2'-phenyl-[1,3]dioxan-4'-yl)but-2-enal

(Z)-(4S,2'S,4'S)-4-methoxymethoxy-4-(2'-phenyl-[1,3]dioxan-4'-yl)but-2-en-1-ol

(Z,Z)-(1S,2S,4S)-4-(5-bromo-1-methoxymethoxy-penta-2,4-dienyl)-2-phenyl[1,3]dioxane