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

Base Information

• Chemical Name: (4S,2'S,4'S)-acetic acid 4-hydroxy-4-(2'-phenyl-[1,3]dioxan-4'-yl)but-2-ynyl ester
• CAS No.: 760210-79-5
• Molecular Formula: C₁₆H₁₈O₅
• Molecular Weight: 290.316
• Mol file: 760210-79-5.mol

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

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

There total 1 articles about (4S,2'S,4'S)-acetic acid 4-hydroxy-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: 89.0%

Propargyl acetate (627-09-8) + (2S,4S)-2-phenyl-1,3-dioxane-4-carboxaldehyde (145958-02-7) → (4S,2'S,4'S)-acetic acid 4-hydroxy-4-(2'-phenyl-[1,3]dioxan-4'-yl)but-2-ynyl ester (760210-79-5)

Guidance literature:

With zinc trifluoromethanesulfonate; (+)-N-methylephedrine; triethylamine; In toluene; at 20 ℃; for 1.5h;

DOI:10.1021/ja047190o

Reference yield:

(4S,2'S,4'S)-acetic acid 4-hydroxy-4-(2'-phenyl-[1,3]dioxan-4'-yl)but-2-ynyl ester (760210-79-5) → (Z,Z)-(3S,4S)-2-ethynyl-6-hydroxy benzoic acid 3-(1-benzyloxy-8-bromo-4-methoxymethoxy-octa-5,7-dienyl) ester (760210-88-6)

Guidance literature:

Multi-step reaction with 9 steps

1: i-Pr₂NEt / CH₂Cl₂ / 20 °C

2: K₂CO₃; methanol / 0.5 h / 0 °C

3: 1.42 g / H₂; quinoline / Lindlar's catalyst / methanol / 24 h / 20 °C

4: IBX; DMSO / 1 h / 20 °C

5: 1.10 g / PPh₃; Et₃N / CH₂Cl₂ / 0.75 h / 0 °C

6: 88 percent / n-Bu₃SnH; Pd(PPh₃)4 / benzene / 20 °C

7: 75 percent / DIBALH / CH₂Cl₂; toluene / 0.17 h / 0 °C

8: NaHMDS / tetrahydrofuran / 5 h / -20 - 0 °C

9: 355 mg / TBAF / tetrahydrofuran / 1.5 h / 0 °C

With quinoline; methanol; tetrakis(triphenylphosphine) palladium⁽⁰⁾; tetrabutyl ammonium fluoride; hydrogen; tri-n-butyl-tin hydride; sodium hexamethyldisilazane; diisobutylaluminium hydride; potassium carbonate; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; Lindlar's catalyst; In tetrahydrofuran; methanol; dichloromethane; toluene; benzene;

DOI:10.1021/ja047190o

Reference yield:

(4S,2'S,4'S)-acetic acid 4-hydroxy-4-(2'-phenyl-[1,3]dioxan-4'-yl)but-2-ynyl ester (760210-79-5) → (1E,3Z,5Z)-(7S,8S)-5-(10-benzyloxy-8-hydroxy-7-methoxymethoxydeca-1,3,5-trienyl)-2,2-dimethylbenzo[1,3]dioxin-4-one

Guidance literature:

Multi-step reaction with 8 steps

1: i-Pr₂NEt / CH₂Cl₂ / 20 °C

2: K₂CO₃; methanol / 0.5 h / 0 °C

3: 1.42 g / H₂; quinoline / Lindlar's catalyst / methanol / 24 h / 20 °C

4: IBX; DMSO / 1 h / 20 °C

5: 1.10 g / PPh₃; Et₃N / CH₂Cl₂ / 0.75 h / 0 °C

6: 88 percent / n-Bu₃SnH; Pd(PPh₃)4 / benzene / 20 °C

7: 75 percent / DIBALH / CH₂Cl₂; toluene / 0.17 h / 0 °C

8: 93 percent / Pd(PPh₃)4; aq. Cs₂CO₃ / tetrahydrofuran / 4 h / Heating

With quinoline; methanol; tetrakis(triphenylphosphine) palladium⁽⁰⁾; hydrogen; tri-n-butyl-tin hydride; diisobutylaluminium hydride; potassium carbonate; caesium carbonate; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; Lindlar's catalyst; In tetrahydrofuran; methanol; dichloromethane; toluene; benzene; 8: Suzuki cross-coupling;

DOI:10.1021/ja047190o

upstream raw materials:

Propargyl acetate

(2S,4S)-2-phenyl-1,3-dioxane-4-carboxaldehyde

Downstream raw materials:

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

(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

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