Benzoic acid (2S,4S,6R)-6-[(2R,3R)-3-benzyloxy-2-(4-methoxy-benzyloxy)-butyl]-2-methoxy-2-[(E)-4-(4-methoxy-benzyloxy)-1,1-dimethyl-but-2-enyl]-3-oxo-tetrahydro-pyran-4-yl ester

Base Information

• Chemical Name: Benzoic acid (2S,4S,6R)-6-[(2R,3R)-3-benzyloxy-2-(4-methoxy-benzyloxy)-butyl]-2-methoxy-2-[(E)-4-(4-methoxy-benzyloxy)-1,1-dimethyl-but-2-enyl]-3-oxo-tetrahydro-pyran-4-yl ester
• CAS No.: 588728-62-5
• Molecular Formula: C₄₆H₅₄O₁₀
• Molecular Weight: 766.929

Synonyms:Benzoic acid (2S,4S,6R)-6-[(2R,3R)-3-benzyloxy-2-(4-methoxy-benzyloxy)-butyl]-2-methoxy-2-[(E)-4-(4-methoxy-benzyloxy)-1,1-dimethyl-but-2-enyl]-3-oxo-tetrahydro-pyran-4-yl ester

Chemical Property of Benzoic acid (2S,4S,6R)-6-[(2R,3R)-3-benzyloxy-2-(4-methoxy-benzyloxy)-butyl]-2-methoxy-2-[(E)-4-(4-methoxy-benzyloxy)-1,1-dimethyl-but-2-enyl]-3-oxo-tetrahydro-pyran-4-yl ester

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Technology Process of Benzoic acid (2S,4S,6R)-6-[(2R,3R)-3-benzyloxy-2-(4-methoxy-benzyloxy)-butyl]-2-methoxy-2-[(E)-4-(4-methoxy-benzyloxy)-1,1-dimethyl-but-2-enyl]-3-oxo-tetrahydro-pyran-4-yl ester

There total 20 articles about Benzoic acid (2S,4S,6R)-6-[(2R,3R)-3-benzyloxy-2-(4-methoxy-benzyloxy)-butyl]-2-methoxy-2-[(E)-4-(4-methoxy-benzyloxy)-1,1-dimethyl-but-2-enyl]-3-oxo-tetrahydro-pyran-4-yl 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:

Benzoic acid (2S,3S,4S,6R)-6-[(2R,3R)-3-benzyloxy-2-(4-methoxy-benzyloxy)-butyl]-3-hydroxy-2-methoxy-2-[(E)-4-(4-methoxy-benzyloxy)-1,1-dimethyl-but-2-enyl]-tetrahydro-pyran-4-yl ester → Benzoic acid (2S,4S,6R)-6-[(2R,3R)-3-benzyloxy-2-(4-methoxy-benzyloxy)-butyl]-2-methoxy-2-[(E)-4-(4-methoxy-benzyloxy)-1,1-dimethyl-but-2-enyl]-3-oxo-tetrahydro-pyran-4-yl ester (588728-62-5)

Guidance literature:

With Dess-Martin periodane; In dichloromethane; at 20 ℃; for 5.5h;

DOI:10.1021/ol0355332

Reference yield:

(E)-methyl 5-bromo-2,2-dimethylpent-3-enoate (588728-59-0) → Benzoic acid (2S,4S,6R)-6-[(2R,3R)-3-benzyloxy-2-(4-methoxy-benzyloxy)-butyl]-2-methoxy-2-[(E)-4-(4-methoxy-benzyloxy)-1,1-dimethyl-but-2-enyl]-3-oxo-tetrahydro-pyran-4-yl ester (588728-62-5)

Guidance literature:

Multi-step reaction with 10 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: 4-dimethylaminopyridine / CH₂Cl₂ / 0.5 h / -10 °C

10.1: 121 mg / Dess-Martin periodinane / CH₂Cl₂ / 5.5 h / 20 °C

With dmap; sodium tetrahydroborate; cerium(III) chloride; tetrapropylammonium perruthennate; sodium hydride; sodium hydrogencarbonate; Dess-Martin periodane; toluene-4-sulfonic acid; pyridine hydrogenfluoride; 4-methylmorpholine N-oxide; 3-chloro-benzenecarboperoxoic acid; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; toluene; 7.1: Luche reduction / 10.1: Dess-Martin oxidation;

DOI:10.1021/ol0355332

Reference yield:

(3R,4R)-4-Benzyloxy-3-(4-methoxy-benzyloxy)-pentanal (206255-41-6) → Benzoic acid (2S,4S,6R)-6-[(2R,3R)-3-benzyloxy-2-(4-methoxy-benzyloxy)-butyl]-2-methoxy-2-[(E)-4-(4-methoxy-benzyloxy)-1,1-dimethyl-but-2-enyl]-3-oxo-tetrahydro-pyran-4-yl ester (588728-62-5)

Guidance literature:

Multi-step reaction with 7 steps

1.1: LDA / tetrahydrofuran; hexane / 0.33 h / -78 °C

1.2: 87 percent / tetrahydrofuran; hexane / 0.25 h / -78 °C

2.1: LDA / tetrahydrofuran; hexane / 0.33 h / -78 °C

2.2: 61 percent / tetrahydrofuran; hexane / 0.5 h / -78 °C

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

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

5.1: 0.158 g / m-chloroperoxybenzoic acid; NaHCO₃ / CH₂Cl₂ / 0.75 h / 0 - 20 °C

6.1: 4-dimethylaminopyridine / CH₂Cl₂ / 0.5 h / -10 °C

7.1: 121 mg / Dess-Martin periodinane / CH₂Cl₂ / 5.5 h / 20 °C

With dmap; sodium tetrahydroborate; cerium(III) chloride; sodium hydrogencarbonate; Dess-Martin periodane; toluene-4-sulfonic acid; 3-chloro-benzenecarboperoxoic acid; lithium diisopropyl amide; In tetrahydrofuran; methanol; hexane; dichloromethane; toluene; 4.1: Luche reduction / 7.1: Dess-Martin oxidation;

DOI:10.1021/ol0355332

upstream raw materials:

benzoyl chloride

(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:

(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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