Acetic acid (E)-(1S,2R)-2-acetoxy-1-((S)-2,3-dihydroxy-propyl)-4-phenyl-but-3-enyl ester

Base Information

• Chemical Name: Acetic acid (E)-(1S,2R)-2-acetoxy-1-((S)-2,3-dihydroxy-propyl)-4-phenyl-but-3-enyl ester
• CAS No.: 106976-87-8
• Molecular Formula: C₁₇H₂₂O₆
• Molecular Weight: 322.358
• Mol file: 106976-87-8.mol

Synonyms:Acetic acid (E)-(1S,2R)-2-acetoxy-1-((S)-2,3-dihydroxy-propyl)-4-phenyl-but-3-enyl ester

Chemical Property of Acetic acid (E)-(1S,2R)-2-acetoxy-1-((S)-2,3-dihydroxy-propyl)-4-phenyl-but-3-enyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acetic acid (E)-(1S,2R)-2-acetoxy-1-((S)-2,3-dihydroxy-propyl)-4-phenyl-but-3-enyl ester

There total 5 articles about Acetic acid (E)-(1S,2R)-2-acetoxy-1-((S)-2,3-dihydroxy-propyl)-4-phenyl-but-3-enyl 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: 85.0%

Acetic acid (E)-(1S,2R)-2-acetoxy-1-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-4-phenyl-but-3-enyl ester (106976-86-7) → Acetic acid (E)-(1S,2R)-2-acetoxy-1-((S)-2,3-dihydroxy-propyl)-4-phenyl-but-3-enyl ester (106976-87-8)

Guidance literature:

With hydrogenchloride; In tetrahydrofuran; methanol; at 23 ℃; for 6h;

DOI:10.1021/jo00386a034

Reference yield:

1,2-(isopropylidenedioxy)-5-acetoxy-7-phenylhept-6-en-4-one (106976-80-1,106976-81-2) → Acetic acid (E)-(1S,2R)-2-acetoxy-1-(2,3-dihydroxy-propyl)-4-phenyl-but-3-enyl ester (106976-87-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) D-glucose, 2.) 2N NaOH / 1.) bakers' yeast, ethanol, water, 25-28 deg C, 12 h, 2.) methanol, 12 h

2: CH₂Cl₂; pyridine / 12 h / 23 °C

3: 1percent HCl in methanol / methanol; tetrahydrofuran / 6 h / 23 °C

With hydrogenchloride; sodium hydroxide; D-glucose; In tetrahydrofuran; pyridine; methanol; dichloromethane;

DOI:10.1021/jo00386a034

Reference yield:

1,2-(isopropylidenedioxy)-5-acetoxy-7-phenylhept-6-en-4-one (106976-80-1,106976-81-2) → Acetic acid (E)-(1S,2R)-2-acetoxy-1-((S)-2,3-dihydroxy-propyl)-4-phenyl-but-3-enyl ester (106976-87-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) D-glucose, 2.) 2N NaOH / 1.) bakers' yeast, ethanol, water, 25-28 deg C, 12 h, 2.) methanol, 12 h

2: 95 percent / pyridine / CH₂Cl₂ / 12 h / 23 °C

3: 85 percent / 1percent HCl in methanol / methanol; tetrahydrofuran / 6 h / 23 °C

With pyridine; hydrogenchloride; sodium hydroxide; D-glucose; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1021/jo00386a034

upstream raw materials:

1,2-(isopropylidenedioxy)-5-acetoxy-7-phenylhept-6-en-4-one

(E)-(2S,3R)-1-(2,2-Dimethyl-[1,3]dioxolan-4-yl)-5-phenyl-pent-4-ene-2,3-diol

Acetic acid (E)-(1S,2R)-2-acetoxy-1-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-4-phenyl-but-3-enyl ester

(E)-(2S,3R)-1-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-5-phenyl-pent-4-ene-2,3-diol

Downstream raw materials:

4-deoxy-D-lyxo-hexopyranose