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

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Chemical Name:(3aS,4S,6R,7aS)-6-[(2R,3R)-3-Benzyloxy-2-(4-methoxy-benzyloxy)-butyl]-4-methoxy-4-[(E)-4-(4-methoxy-benzyloxy)-1,1-dimethyl-but-2-enyl]-tetrahydro-[1,3]dioxolo[4,5-c]pyran-2-one
CAS No.:639786-30-4
Molecular Formula:C₄₀H₅₀O₁₀
Molecular Weight:690.831
Hs Code.:

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

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

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Chemical Property of (3aS,4S,6R,7aS)-6-[(2R,3R)-3-Benzyloxy-2-(4-methoxy-benzyloxy)-butyl]-4-methoxy-4-[(E)-4-(4-methoxy-benzyloxy)-1,1-dimethyl-but-2-enyl]-tetrahydro-[1,3]dioxolo[4,5-c]pyran-2-one

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Technology Process of (3aS,4S,6R,7aS)-6-[(2R,3R)-3-Benzyloxy-2-(4-methoxy-benzyloxy)-butyl]-4-methoxy-4-[(E)-4-(4-methoxy-benzyloxy)-1,1-dimethyl-but-2-enyl]-tetrahydro-[1,3]dioxolo[4,5-c]pyran-2-one

There total 18 articles about (3aS,4S,6R,7aS)-6-[(2R,3R)-3-Benzyloxy-2-(4-methoxy-benzyloxy)-butyl]-4-methoxy-4-[(E)-4-(4-methoxy-benzyloxy)-1,1-dimethyl-but-2-enyl]-tetrahydro-[1,3]dioxolo[4,5-c]pyran-2-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: 93.0%

: 32315-10-9
bis(trichloromethyl) carbonate

: 588728-55-6
(2S,3S,4S,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]-tetrahydro-pyran-3,4-diol

: 639786-30-4
(3aS,4S,6R,7aS)-6-[(2R,3R)-3-Benzyloxy-2-(4-methoxy-benzyloxy)-butyl]-4-methoxy-4-[(E)-4-(4-methoxy-benzyloxy)-1,1-dimethyl-but-2-enyl]-tetrahydro-[1,3]dioxolo[4,5-c]pyran-2-one

Guidance literature:: With pyridine; In dichloromethane; at 0 ℃; for 0.5h;
DOI:10.1021/ol0355332

Reference yield:

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

: 639786-30-4
(3aS,4S,6R,7aS)-6-[(2R,3R)-3-Benzyloxy-2-(4-methoxy-benzyloxy)-butyl]-4-methoxy-4-[(E)-4-(4-methoxy-benzyloxy)-1,1-dimethyl-but-2-enyl]-tetrahydro-[1,3]dioxolo[4,5-c]pyran-2-one

Guidance literature:: Multi-step reaction with 9 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

With pyridine; 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; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; toluene; 7.1: Luche reduction;
DOI:10.1021/ol0355332

Reference yield:

: 206255-41-6
(3R,4R)-4-Benzyloxy-3-(4-methoxy-benzyloxy)-pentanal

: 639786-30-4
(3aS,4S,6R,7aS)-6-[(2R,3R)-3-Benzyloxy-2-(4-methoxy-benzyloxy)-butyl]-4-methoxy-4-[(E)-4-(4-methoxy-benzyloxy)-1,1-dimethyl-but-2-enyl]-tetrahydro-[1,3]dioxolo[4,5-c]pyran-2-one

Guidance literature:: Multi-step reaction with 6 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: 93 percent / pyridine / CH₂Cl₂ / 0.5 h / 0 °C

With pyridine; sodium tetrahydroborate; cerium(III) chloride; sodium hydrogencarbonate; toluene-4-sulfonic acid; 3-chloro-benzenecarboperoxoic acid; lithium diisopropyl amide; In tetrahydrofuran; methanol; hexane; dichloromethane; toluene; 4.1: Luche reduction;
DOI:10.1021/ol0355332