(4aS,7R,7aS)-7-(benzyloxy)-2,2-dimethyldihydro-4H-4a,7a-(methanooxymethano)furo[3,2-d][1,3]dioxin-10-one

Base Information

• Chemical Name: (4aS,7R,7aS)-7-(benzyloxy)-2,2-dimethyldihydro-4H-4a,7a-(methanooxymethano)furo[3,2-d][1,3]dioxin-10-one
• CAS No.: 1429480-86-3
• Molecular Formula: C₁₇H₂₀O₆
• Molecular Weight: 320.342

Synonyms:(4aS,7R,7aS)-7-(benzyloxy)-2,2-dimethyldihydro-4H-4a,7a-(methanooxymethano)furo[3,2-d][1,3]dioxin-10-one

Chemical Property of (4aS,7R,7aS)-7-(benzyloxy)-2,2-dimethyldihydro-4H-4a,7a-(methanooxymethano)furo[3,2-d][1,3]dioxin-10-one

Chemical Property:

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Technology Process of (4aS,7R,7aS)-7-(benzyloxy)-2,2-dimethyldihydro-4H-4a,7a-(methanooxymethano)furo[3,2-d][1,3]dioxin-10-one

There total 8 articles about (4aS,7R,7aS)-7-(benzyloxy)-2,2-dimethyldihydro-4H-4a,7a-(methanooxymethano)furo[3,2-d][1,3]dioxin-10-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: 88.0%

(3R,3aS,6aS)-3-(benzyloxy)tetrahydro-3a-hydroxy-6a-(hydroxymethyl)furo[3,4-b]furan-6(6aH)-one (1429480-85-2) + 2,2-dimethoxy-propane (77-76-9) → (4aS,7R,7aS)-7-(benzyloxy)-2,2-dimethyldihydro-4H-4a,7a-(methanooxymethano)furo[3,2-d][1,3]dioxin-10-one (1429480-86-3)

Guidance literature:

With water; toluene-4-sulfonic acid; In acetone; at 20 ℃; for 12.5h; Inert atmosphere; Reflux;

DOI:10.1021/jo400263w

Reference yield:

benzyl bromide (100-39-0) → (4aS,7R,7aS)-7-(benzyloxy)-2,2-dimethyldihydro-4H-4a,7a-(methanooxymethano)furo[3,2-d][1,3]dioxin-10-one (1429480-86-3)

Guidance literature:

Multi-step reaction with 8 steps

1.1: sodium hydride; tetra-(n-butyl)ammonium iodide / N,N-dimethyl-formamide; mineral oil / 5 h / 0 - 20 °C / Inert atmosphere

2.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 1.5 h / 0 °C / Inert atmosphere

3.1: dirhodium tetraacetate / benzene / 1 h / Inert atmosphere; Reflux

4.1: indium(III) triflate; 1,8-diazabicyclo[5.4.0]undec-7-ene / toluene / 3 h / Inert atmosphere; Reflux

5.1: water; osmium(VIII) oxide; 4-methylmorpholine N-oxide / tetrahydrofuran / 7 h / 20 - 70 °C / Inert atmosphere

6.1: lithium hydroxide / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere

7.1: oxalyl dichloride; N,N-dimethyl-formamide / tetrahydrofuran; dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere

7.2: 1 h / -78 °C / Inert atmosphere

8.1: water; toluene-4-sulfonic acid / acetone / 12.5 h / 20 °C / Inert atmosphere; Reflux

With indium(III) triflate; dirhodium tetraacetate; osmium(VIII) oxide; oxalyl dichloride; water; tetra-(n-butyl)ammonium iodide; sodium hydride; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; N,N-dimethyl-formamide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium hydroxide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; acetone; toluene; mineral oil; benzene;

DOI:10.1021/jo400263w

Reference yield:

1-(((S)-2-(benzyloxy)but-3-ynyloxy)methyl)-4-methoxybenzene (1429480-79-4) → (4aS,7R,7aS)-7-(benzyloxy)-2,2-dimethyldihydro-4H-4a,7a-(methanooxymethano)furo[3,2-d][1,3]dioxin-10-one (1429480-86-3)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 1.5 h / 0 °C / Inert atmosphere

2.1: dirhodium tetraacetate / benzene / 1 h / Inert atmosphere; Reflux

3.1: indium(III) triflate; 1,8-diazabicyclo[5.4.0]undec-7-ene / toluene / 3 h / Inert atmosphere; Reflux

4.1: water; osmium(VIII) oxide; 4-methylmorpholine N-oxide / tetrahydrofuran / 7 h / 20 - 70 °C / Inert atmosphere

5.1: lithium hydroxide / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere

6.1: oxalyl dichloride; N,N-dimethyl-formamide / tetrahydrofuran; dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere

6.2: 1 h / -78 °C / Inert atmosphere

7.1: water; toluene-4-sulfonic acid / acetone / 12.5 h / 20 °C / Inert atmosphere; Reflux

With indium(III) triflate; dirhodium tetraacetate; osmium(VIII) oxide; oxalyl dichloride; water; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; N,N-dimethyl-formamide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium hydroxide; In tetrahydrofuran; dichloromethane; acetone; toluene; benzene;

DOI:10.1021/jo400263w

upstream raw materials:

1-(((S)-2-(benzyloxy)but-3-ynyloxy)methyl)-4-methoxybenzene

benzyl bromide

(S)-2-(benzyloxy)but-3-yn-1-ol

dimethyl 2-((S)-2-(benzyloxy)but-3-ynyloxy)malonate

Downstream raw materials:

((4aS,7R,7aS)-7-(benzyloxy)-4a-(dodec-1-enyl)-tetrahydro-2,2-dimethyl-4H-furo[3,2-d][1,3]dioxin-7a-yl)methanol

methyl (4aS,7R,7aS)-7-(benzyloxy)-4a-(dodec-1-enyl)-tetrahydro-2,2-dimethyl-4H-furo[3,2-d][1,3]dioxine-7a-carboxylate

C₂₆H₄₂O₆

dimethyl (2R,3S,4R)-4-(benzyloxy)-2-dodecyltetrahydro-3-hydroxyfuran-2,3-dicarboxylate

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