(E)-(5S,6R)-5,6-Bis-benzyloxy-6-((S)-2-oxo-[1,3]dioxolan-4-yl)-hex-2-enoic acid ethyl ester

Base Information

• Chemical Name: (E)-(5S,6R)-5,6-Bis-benzyloxy-6-((S)-2-oxo-[1,3]dioxolan-4-yl)-hex-2-enoic acid ethyl ester
• CAS No.: 616895-57-9
• Molecular Formula: C₂₅H₂₈O₇
• Molecular Weight: 440.493
• Mol file: 616895-57-9.mol

Synonyms:(E)-(5S,6R)-5,6-Bis-benzyloxy-6-((S)-2-oxo-[1,3]dioxolan-4-yl)-hex-2-enoic acid ethyl ester

Chemical Property of (E)-(5S,6R)-5,6-Bis-benzyloxy-6-((S)-2-oxo-[1,3]dioxolan-4-yl)-hex-2-enoic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-(5S,6R)-5,6-Bis-benzyloxy-6-((S)-2-oxo-[1,3]dioxolan-4-yl)-hex-2-enoic acid ethyl ester

There total 5 articles about (E)-(5S,6R)-5,6-Bis-benzyloxy-6-((S)-2-oxo-[1,3]dioxolan-4-yl)-hex-2-enoic acid ethyl 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: 51.0%

benzyl alcohol (100-51-6,185532-71-2) + (E)-(5S,6R)-5,6-Dihydroxy-6-((S)-2-oxo-[1,3]dioxolan-4-yl)-hex-2-enoic acid ethyl ester (616895-56-8) → (E)-(5S,6R)-5,6-Bis-benzyloxy-6-((S)-2-oxo-[1,3]dioxolan-4-yl)-hex-2-enoic acid ethyl ester (616895-57-9)

Guidance literature:

With 2,6-di-tert-butyl-4-methylpyridine; trifluoromethylsulfonic anhydride; In dichloromethane; at -78 ℃;

DOI:10.1016/S0040-4020(03)00370-3

Reference yield:

((4R,5S,4'S)-2,2,2',2'-Tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-acetaldehyde → (E)-(5S,6R)-5,6-Bis-benzyloxy-6-((S)-2-oxo-[1,3]dioxolan-4-yl)-hex-2-enoic acid ethyl ester (616895-57-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 85 percent / tetrahydrofuran / 18 h / 20 °C

2: TsOH / ethanol; H₂O

3: pyridine / CH₂Cl₂

4: 84 percent / CuCl₂ / acetonitrile

5: 51 percent / Tf₂O; 2,6-di-tert-butyl-4-methylpyridine / CH₂Cl₂ / -78 °C

With pyridine; 2,6-di-tert-butyl-4-methylpyridine; trifluoromethylsulfonic anhydride; toluene-4-sulfonic acid; copper dichloride; In tetrahydrofuran; ethanol; dichloromethane; water; acetonitrile; 1: Wittig olefination;

DOI:10.1016/S0040-4020(03)00370-3

Reference yield:

(5S,6R,7S)-5,6:7,8-diisopropylidene-5,6,7,8-tetrahydroxyoct-2-enoic acid ethyl ester (393530-29-5) → (E)-(5S,6R)-5,6-Bis-benzyloxy-6-((S)-2-oxo-[1,3]dioxolan-4-yl)-hex-2-enoic acid ethyl ester (616895-57-9)

Guidance literature:

Multi-step reaction with 4 steps

1: TsOH / ethanol; H₂O

2: pyridine / CH₂Cl₂

3: 84 percent / CuCl₂ / acetonitrile

4: 51 percent / Tf₂O; 2,6-di-tert-butyl-4-methylpyridine / CH₂Cl₂ / -78 °C

With pyridine; 2,6-di-tert-butyl-4-methylpyridine; trifluoromethylsulfonic anhydride; toluene-4-sulfonic acid; copper dichloride; In ethanol; dichloromethane; water; acetonitrile;

DOI:10.1016/S0040-4020(03)00370-3

upstream raw materials:

benzyl alcohol

(E)-(5S,6R)-5,6-Dihydroxy-6-((S)-2-oxo-[1,3]dioxolan-4-yl)-hex-2-enoic acid ethyl ester

(5S,6R,7S)-5,6:7,8-diisopropylidene-5,6,7,8-tetrahydroxyoct-2-enoic acid ethyl ester

(E)-4-((4R,5S,4'S)-2,2-Dimethyl-2'-oxo-[4,4']bi[[1,3]dioxolanyl]-5-yl)-but-2-enoic acid ethyl ester

Downstream raw materials:

[2,3-di-O-benzyl-4,6-dideoxy-6-(methoxycarbonyl)-D-gluco-β-C-pyranosyl]aldehyde

{(2S,4S,5R,6S)-4,5-Bis-benzyloxy-6-[(E)-2-((1S,2S,3S)-2-hydroxymethyl-3-methyl-cyclopropyl)-vinyl]-tetrahydro-pyran-2-yl}-acetic acid methyl ester

[2,3-di-O-benzyl-4,6-dideoxy-6-(methoxycarbonyl)-D-gluco-β-C-pyranosyl]methanol