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

Base Information

Chemical Name:4-[(2S,4R)-4-((E)-(S)-1-Benzyloxy-7-hydroxy-hept-3-enyl)-[1,3]dioxolan-2-yl]-benzoic acid
CAS No.:211691-96-2
Molecular Formula:C₂₄H₂₈O₆
Molecular Weight:412.483
Hs Code.:

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

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

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

There total 10 articles about 4-[(2S,4R)-4-((E)-(S)-1-Benzyloxy-7-hydroxy-hept-3-enyl)-[1,3]dioxolan-2-yl]-benzoic acid 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:

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

: 211691-96-2
4-[(2S,4R)-4-((E)-(S)-1-Benzyloxy-7-hydroxy-hept-3-enyl)-[1,3]dioxolan-2-yl]-benzoic acid

Guidance literature:: With lithium hydroxide; water; In tetrahydrofuran; methanol; Yield given;
DOI:10.1002/(SICI)1521-3773(19980619)37:11<1566::AID-ANIE1566>3.0.CO;2-U

Reference yield:

: 79364-35-5
(S)-1-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)but-3-en-1-ol

: 211691-96-2
4-[(2S,4R)-4-((E)-(S)-1-Benzyloxy-7-hydroxy-hept-3-enyl)-[1,3]dioxolan-2-yl]-benzoic acid

Guidance literature:: Multi-step reaction with 9 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

9: H₂O, LiOH / methanol; tetrahydrofuran

With 1H-imidazole; lithium hydroxide; lithium aluminium tetrahydride; 4 A molecular sieve; water; sodium hydride; toluene-4-sulfonic acid; ozone; acetic acid; propionic acid; triethylamine; triphenylphosphine; In tetrahydrofuran; methanol; 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:

: 103795-36-4
(3S,4R)-3-O-benzyl-4,5-O-isopropylidene-3,4,5-trihydroxypentanal

: 211691-96-2
4-[(2S,4R)-4-((E)-(S)-1-Benzyloxy-7-hydroxy-hept-3-enyl)-[1,3]dioxolan-2-yl]-benzoic acid

Guidance literature:: Multi-step reaction with 7 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

7: H₂O, LiOH / methanol; tetrahydrofuran

With lithium hydroxide; lithium aluminium tetrahydride; 4 A molecular sieve; water; toluene-4-sulfonic acid; acetic acid; propionic acid; triethylamine; In tetrahydrofuran; methanol; dichloromethane; toluene;
DOI:10.1002/(SICI)1521-3773(19980619)37:11<1566::AID-ANIE1566>3.0.CO;2-U