(E)-4-[(3aS,4S,6R,7aS)-6-((2R,3R)-3-Benzyloxy-2-hydroxy-butyl)-4-methoxy-2-oxo-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-yl]-4-methyl-pent-2-enal

Base Information

Chemical Name:(E)-4-[(3aS,4S,6R,7aS)-6-((2R,3R)-3-Benzyloxy-2-hydroxy-butyl)-4-methoxy-2-oxo-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-yl]-4-methyl-pent-2-enal
CAS No.:639786-31-5
Molecular Formula:C₂₄H₃₂O₈
Molecular Weight:448.513
Hs Code.:

Synonyms:(E)-4-[(3aS,4S,6R,7aS)-6-((2R,3R)-3-Benzyloxy-2-hydroxy-butyl)-4-methoxy-2-oxo-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-yl]-4-methyl-pent-2-enal

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Chemical Property of (E)-4-[(3aS,4S,6R,7aS)-6-((2R,3R)-3-Benzyloxy-2-hydroxy-butyl)-4-methoxy-2-oxo-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-yl]-4-methyl-pent-2-enal

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Technology Process of (E)-4-[(3aS,4S,6R,7aS)-6-((2R,3R)-3-Benzyloxy-2-hydroxy-butyl)-4-methoxy-2-oxo-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-yl]-4-methyl-pent-2-enal

There total 21 articles about (E)-4-[(3aS,4S,6R,7aS)-6-((2R,3R)-3-Benzyloxy-2-hydroxy-butyl)-4-methoxy-2-oxo-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-yl]-4-methyl-pent-2-enal 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: 70.0%

: 639786-36-0
(3aS,4S,6R,7aS)-6-((2R,3R)-3-Benzyloxy-2-hydroxy-butyl)-4-((E)-4-hydroxy-1,1-dimethyl-but-2-enyl)-4-methoxy-tetrahydro-[1,3]dioxolo[4,5-c]pyran-2-one

: 639786-31-5
(E)-4-[(3aS,4S,6R,7aS)-6-((2R,3R)-3-Benzyloxy-2-hydroxy-butyl)-4-methoxy-2-oxo-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-yl]-4-methyl-pent-2-enal

Guidance literature:: With manganese(IV) oxide; In dichloromethane; for 3h;
DOI:10.1021/ol0355332

Reference yield:

: 76352-72-2
methyl 2,2-dimethyl-4-pentenoate

: 639786-31-5
(E)-4-[(3aS,4S,6R,7aS)-6-((2R,3R)-3-Benzyloxy-2-hydroxy-butyl)-4-methoxy-2-oxo-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-yl]-4-methyl-pent-2-enal

Guidance literature:: Multi-step reaction with 12 steps

1.1: 74 percent / N-bromosuccinimide; dibenzoylperoxide / CCl₄ / 2 h / Heating

2.1: NaH / tetrahydrofuran / 6 h / 35 °C

2.2: 6.54 g / PhMgBr / tetrahydrofuran / 1 h / -20 °C

3.1: 99 percent / tetrahydrofuran; diethyl ether / 1 h / -78 °C

4.1: LDA / tetrahydrofuran; hexane / -78 - 20 °C

4.2: 96 percent / tetrahydrofuran; hexane / 0.25 h / -78 °C

5.1: 55 percent / N-methylmorpholine N-oxide; tetrapropyl ammonium perruthenate / CH₂Cl₂ / 0.5 h

6.1: 70 percent / HF*pyridine / tetrahydrofuran / 168 h / 20 °C

7.1: p-toluenesulfonic acid / toluene / 10 h / 20 °C

8.1: NaBH₄; CeCl₃*7H₂O / methanol / -20 °C

9.1: 0.158 g / m-chloroperoxybenzoic acid; NaHCO₃ / CH₂Cl₂ / 0.75 h / 0 - 20 °C

10.1: 93 percent / pyridine / CH₂Cl₂ / 0.5 h / 0 °C

11.1: 66 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH₂Cl₂; H₂O / 2 h

12.1: 70 percent / MnO₂ / CH₂Cl₂ / 3 h

With pyridine; manganese(IV) oxide; sodium tetrahydroborate; N-Bromosuccinimide; cerium(III) chloride; tetrapropylammonium perruthennate; sodium hydride; sodium hydrogencarbonate; toluene-4-sulfonic acid; pyridine hydrogenfluoride; 4-methylmorpholine N-oxide; 3-chloro-benzenecarboperoxoic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium diisopropyl amide; dibenzoyl peroxide; In tetrahydrofuran; methanol; tetrachloromethane; diethyl ether; hexane; dichloromethane; water; toluene; 8.1: Luche reduction;
DOI:10.1021/ol0355332

Reference yield:

: 588728-59-0
(E)-methyl 5-bromo-2,2-dimethylpent-3-enoate

: 639786-31-5
(E)-4-[(3aS,4S,6R,7aS)-6-((2R,3R)-3-Benzyloxy-2-hydroxy-butyl)-4-methoxy-2-oxo-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-yl]-4-methyl-pent-2-enal

Guidance literature:: Multi-step reaction with 11 steps

1.1: NaH / tetrahydrofuran / 6 h / 35 °C

1.2: 6.54 g / PhMgBr / tetrahydrofuran / 1 h / -20 °C

2.1: 99 percent / tetrahydrofuran; diethyl ether / 1 h / -78 °C

3.1: LDA / tetrahydrofuran; hexane / -78 - 20 °C

3.2: 96 percent / tetrahydrofuran; hexane / 0.25 h / -78 °C

4.1: 55 percent / N-methylmorpholine N-oxide; tetrapropyl ammonium perruthenate / CH₂Cl₂ / 0.5 h

5.1: 70 percent / HF*pyridine / tetrahydrofuran / 168 h / 20 °C

6.1: p-toluenesulfonic acid / toluene / 10 h / 20 °C

7.1: NaBH₄; CeCl₃*7H₂O / methanol / -20 °C

8.1: 0.158 g / m-chloroperoxybenzoic acid; NaHCO₃ / CH₂Cl₂ / 0.75 h / 0 - 20 °C

9.1: 93 percent / pyridine / CH₂Cl₂ / 0.5 h / 0 °C

10.1: 66 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH₂Cl₂; H₂O / 2 h

11.1: 70 percent / MnO₂ / CH₂Cl₂ / 3 h

With pyridine; manganese(IV) oxide; sodium tetrahydroborate; cerium(III) chloride; tetrapropylammonium perruthennate; sodium hydride; sodium hydrogencarbonate; toluene-4-sulfonic acid; pyridine hydrogenfluoride; 4-methylmorpholine N-oxide; 3-chloro-benzenecarboperoxoic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; toluene; 7.1: Luche reduction;
DOI:10.1021/ol0355332