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

Base Information

• Chemical Name: 4-[(2R,4R)-4-((E)-(S)-7-Acetoxy-1-benzyloxy-hept-3-enyl)-[1,3]dioxolan-2-yl]-benzoic acid methyl ester
• CAS No.: 211692-24-9
• Molecular Formula: C₂₇H₃₂O₇
• Molecular Weight: 468.547

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

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

Chemical Property:

Purity/Quality:

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

There total 9 articles about 4-[(2R,4R)-4-((E)-(S)-7-Acetoxy-1-benzyloxy-hept-3-enyl)-[1,3]dioxolan-2-yl]-benzoic acid methyl 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:

(S)-1-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)but-3-en-1-ol (79364-35-5) → 4-[(2R,4R)-4-((E)-(S)-7-Acetoxy-1-benzyloxy-hept-3-enyl)-[1,3]dioxolan-2-yl]-benzoic acid methyl ester (211692-24-9)

Guidance literature:

Multi-step reaction with 8 steps

1: NaH, imidazole / dimethylformamide

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

3: tetrahydrofuran / 0 °C

4: 79 percent / EtCO₂H / toluene / Heating

5: LiAlH₄ / tetrahydrofuran / 0 °C

6: Et₃N / CH₂Cl₂

7: AcOH, H₂O

8: TsOH, molecular sieves 4 Angstroem

With 1H-imidazole; lithium aluminium tetrahydride; 4 A molecular sieve; water; sodium hydride; toluene-4-sulfonic acid; ozone; acetic acid; propionic acid; triethylamine; triphenylphosphine; In tetrahydrofuran; dichloromethane; 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) → 4-[(2R,4R)-4-((E)-(S)-7-Acetoxy-1-benzyloxy-hept-3-enyl)-[1,3]dioxolan-2-yl]-benzoic acid methyl ester (211692-24-9)

Guidance literature:

Multi-step reaction with 6 steps

1: tetrahydrofuran / 0 °C

2: 79 percent / EtCO₂H / toluene / Heating

3: LiAlH₄ / tetrahydrofuran / 0 °C

4: Et₃N / CH₂Cl₂

5: AcOH, H₂O

6: TsOH, molecular sieves 4 Angstroem

With lithium aluminium tetrahydride; 4 A molecular sieve; water; toluene-4-sulfonic acid; acetic acid; propionic acid; triethylamine; In tetrahydrofuran; dichloromethane; toluene;

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

Reference yield:

(R)-4-((S)-1-(benzyloxy)but-3-ene-1-yl)-2,2-dimethyl-1,3-dioxypentane (87604-53-3) → 4-[(2R,4R)-4-((E)-(S)-7-Acetoxy-1-benzyloxy-hept-3-enyl)-[1,3]dioxolan-2-yl]-benzoic acid methyl ester (211692-24-9)

Guidance literature:

Multi-step reaction with 7 steps

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

2: tetrahydrofuran / 0 °C

3: 79 percent / EtCO₂H / toluene / Heating

4: LiAlH₄ / tetrahydrofuran / 0 °C

5: Et₃N / CH₂Cl₂

6: AcOH, H₂O

7: TsOH, molecular sieves 4 Angstroem

With lithium aluminium tetrahydride; 4 A molecular sieve; water; toluene-4-sulfonic acid; ozone; acetic acid; propionic acid; triethylamine; triphenylphosphine; In tetrahydrofuran; dichloromethane; toluene;

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

upstream raw materials:

methyl 4-formylbenzoate

Acetic acid (E)-(7S,8R)-7-benzyloxy-8,9-dihydroxy-non-4-enyl ester

(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:

(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

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

C₂₄H₂₆O₆

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

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