(R)-2-[(2R,3R)-3-Benzyloxy-2-(4-methoxy-benzyloxy)-butyl]-6-[(E)-4-(4-methoxy-benzyloxy)-1,1-dimethyl-but-2-enyl]-2,3-dihydro-pyran-4-one

Base Information

• Chemical Name: (R)-2-[(2R,3R)-3-Benzyloxy-2-(4-methoxy-benzyloxy)-butyl]-6-[(E)-4-(4-methoxy-benzyloxy)-1,1-dimethyl-but-2-enyl]-2,3-dihydro-pyran-4-one
• CAS No.: 627091-01-4
• Molecular Formula: C₃₈H₄₆O₇
• Molecular Weight: 614.779

Synonyms:(R)-2-[(2R,3R)-3-Benzyloxy-2-(4-methoxy-benzyloxy)-butyl]-6-[(E)-4-(4-methoxy-benzyloxy)-1,1-dimethyl-but-2-enyl]-2,3-dihydro-pyran-4-one

Chemical Property of (R)-2-[(2R,3R)-3-Benzyloxy-2-(4-methoxy-benzyloxy)-butyl]-6-[(E)-4-(4-methoxy-benzyloxy)-1,1-dimethyl-but-2-enyl]-2,3-dihydro-pyran-4-one

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Technology Process of (R)-2-[(2R,3R)-3-Benzyloxy-2-(4-methoxy-benzyloxy)-butyl]-6-[(E)-4-(4-methoxy-benzyloxy)-1,1-dimethyl-but-2-enyl]-2,3-dihydro-pyran-4-one

There total 16 articles about (R)-2-[(2R,3R)-3-Benzyloxy-2-(4-methoxy-benzyloxy)-butyl]-6-[(E)-4-(4-methoxy-benzyloxy)-1,1-dimethyl-but-2-enyl]-2,3-dihydro-pyran-4-one 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:

(E)-(11R,12R)-12-Benzyloxy-9-hydroxy-1,11-bis-(4-methoxy-benzyloxy)-4,4-dimethyl-tridec-2-ene-5,7-dione → (S)-2-[(2R,3R)-3-Benzyloxy-2-(4-methoxy-benzyloxy)-butyl]-6-[(E)-4-(4-methoxy-benzyloxy)-1,1-dimethyl-but-2-enyl]-2,3-dihydro-pyran-4-one + (R)-2-[(2R,3R)-3-Benzyloxy-2-(4-methoxy-benzyloxy)-butyl]-6-[(E)-4-(4-methoxy-benzyloxy)-1,1-dimethyl-but-2-enyl]-2,3-dihydro-pyran-4-one (627091-01-4)

Guidance literature:

With toluene-4-sulfonic acid; In toluene; at 20 ℃; for 10h;

DOI:10.1021/ol0355332

Reference yield:

methyl 2,2-dimethyl-4-pentenoate (76352-72-2) → (R)-2-[(2R,3R)-3-Benzyloxy-2-(4-methoxy-benzyloxy)-butyl]-6-[(E)-4-(4-methoxy-benzyloxy)-1,1-dimethyl-but-2-enyl]-2,3-dihydro-pyran-4-one (627091-01-4)

Guidance literature:

Multi-step reaction with 7 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

With N-Bromosuccinimide; tetrapropylammonium perruthennate; sodium hydride; toluene-4-sulfonic acid; pyridine hydrogenfluoride; 4-methylmorpholine N-oxide; lithium diisopropyl amide; dibenzoyl peroxide; In tetrahydrofuran; tetrachloromethane; diethyl ether; hexane; dichloromethane; toluene;

DOI:10.1021/ol0355332

Reference yield:

(E)-methyl 5-bromo-2,2-dimethylpent-3-enoate (588728-59-0) → (R)-2-[(2R,3R)-3-Benzyloxy-2-(4-methoxy-benzyloxy)-butyl]-6-[(E)-4-(4-methoxy-benzyloxy)-1,1-dimethyl-but-2-enyl]-2,3-dihydro-pyran-4-one (627091-01-4)

Guidance literature:

Multi-step reaction with 6 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

With tetrapropylammonium perruthennate; sodium hydride; toluene-4-sulfonic acid; pyridine hydrogenfluoride; 4-methylmorpholine N-oxide; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; toluene;

DOI:10.1021/ol0355332

upstream raw materials:

methyl 2,2-dimethyl-4-pentenoate

(3R,4R)-4-Benzyloxy-3-(4-methoxy-benzyloxy)-pentanal

(E)-methyl 5-bromo-2,2-dimethylpent-3-enoate

(E)-6-(4-Methoxy-benzyloxy)-3,3-dimethyl-hex-4-en-2-one

Downstream raw materials:

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

(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

(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

(2S,6S)-6-[(2R,3R)-3-Benzyloxy-2-(4-methoxy-benzyloxy)-butyl]-2-methoxy-2-[(E)-4-(4-methoxy-benzyloxy)-1,1-dimethyl-but-2-enyl]-dihydro-pyran-3-one

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