(E)-(S)-7-Benzyloxy-7-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-hept-4-enoic acid ethyl ester

Base Information

• Chemical Name: (E)-(S)-7-Benzyloxy-7-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-hept-4-enoic acid ethyl ester
• CAS No.: 211691-82-6
• Molecular Formula: C₂₁H₃₀O₅
• Molecular Weight: 362.466
• Mol file: 211691-82-6.mol

Synonyms:(E)-(S)-7-Benzyloxy-7-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-hept-4-enoic acid ethyl ester

Chemical Property of (E)-(S)-7-Benzyloxy-7-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-hept-4-enoic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-(S)-7-Benzyloxy-7-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-hept-4-enoic acid ethyl ester

There total 6 articles about (E)-(S)-7-Benzyloxy-7-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-hept-4-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: 79.0%

Triethyl orthoacetate (78-39-7) + (S)-5-Benzyloxy-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-pent-1-en-3-ol (211691-72-4) → (E)-(S)-7-Benzyloxy-7-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-hept-4-enoic acid ethyl ester (211691-82-6)

Guidance literature:

With propionic acid; In toluene; Heating;

DOI:10.1002/(SICI)1521-3773(19980619)37:11<1566::AID-ANIE1566>3.0.CO;2-U

Reference yield:

(S)-1-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)but-3-en-1-ol (79364-35-5) → (E)-(S)-7-Benzyloxy-7-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-hept-4-enoic acid ethyl ester (211691-82-6)

Guidance literature:

Multi-step reaction with 4 steps

1: NaH, imidazole / dimethylformamide

2: 1.) O₃, 2.) PPH₃ / 1.) CH₂Cl₂, 2.) CH₂Cl₂

3: tetrahydrofuran / 0 °C

4: 79 percent / EtCO₂H / toluene / Heating

With 1H-imidazole; sodium hydride; ozone; propionic acid; triphenylphosphine; In tetrahydrofuran; N,N-dimethyl-formamide; toluene;

DOI:10.1002/(SICI)1521-3773(19980619)37:11<1566::AID-ANIE1566>3.0.CO;2-U

Reference yield:

(3S,4R)-3-O-benzyl-4,5-O-isopropylidene-3,4,5-trihydroxypentanal (103795-36-4) → (E)-(S)-7-Benzyloxy-7-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-hept-4-enoic acid ethyl ester (211691-82-6)

Guidance literature:

Multi-step reaction with 2 steps

1: tetrahydrofuran / 0 °C

2: 79 percent / EtCO₂H / toluene / Heating

With propionic acid; In tetrahydrofuran; toluene;

DOI:10.1002/(SICI)1521-3773(19980619)37:11<1566::AID-ANIE1566>3.0.CO;2-U

upstream raw materials:

Triethyl orthoacetate

(S)-5-Benzyloxy-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-pent-1-en-3-ol

(S)-1-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)but-3-en-1-ol

(3S,4R)-3-O-benzyl-4,5-O-isopropylidene-3,4,5-trihydroxypentanal

Downstream raw materials:

4-[(2R,4R)-4-((E)-(S)-7-Acetoxy-1-benzyloxy-hept-3-enyl)-[1,3]dioxolan-2-yl]-benzoic acid methyl ester

4-[(2S,4R)-4-((E)-(S)-1-Benzyloxy-7-hydroxy-hept-3-enyl)-[1,3]dioxolan-2-yl]-benzoic acid

4-[(2R,4R)-4-((E)-(S)-1-Benzyloxy-7-hydroxy-hept-3-enyl)-[1,3]dioxolan-2-yl]-benzoic acid

(2R,5R,6S,8R,9R)-6-Benzyloxy-8,9-dihydroxy-3,13,20-trioxa-tricyclo[13.2.2.1^2,5]icosa-1⁽¹⁸⁾,15⁽¹⁹⁾,16-trien-14-one