(2S,3R,4S,5R)-4-benzyloxy-3-(4-methoxybenzyloxy)-5-methyltetrahydrofuran-2-carbaldehyde

Base Information

Chemical Name:(2S,3R,4S,5R)-4-benzyloxy-3-(4-methoxybenzyloxy)-5-methyltetrahydrofuran-2-carbaldehyde
CAS No.:1346433-78-0
Molecular Formula:C₂₁H₂₄O₅
Molecular Weight:356.419
Hs Code.:

Synonyms:(2S,3R,4S,5R)-4-benzyloxy-3-(4-methoxybenzyloxy)-5-methyltetrahydrofuran-2-carbaldehyde

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Chemical Property of (2S,3R,4S,5R)-4-benzyloxy-3-(4-methoxybenzyloxy)-5-methyltetrahydrofuran-2-carbaldehyde

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Technology Process of (2S,3R,4S,5R)-4-benzyloxy-3-(4-methoxybenzyloxy)-5-methyltetrahydrofuran-2-carbaldehyde

There total 5 articles about (2S,3R,4S,5R)-4-benzyloxy-3-(4-methoxybenzyloxy)-5-methyltetrahydrofuran-2-carbaldehyde 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: 96.0%

: 1346433-74-6
((2R,3S,4S,5R)-4-benzyloxy-3-(4-methoxybenzyloxy)-5-methyltetrohydrofuran-2-yl)methanol

: 1346433-78-0
(2S,3R,4S,5R)-4-benzyloxy-3-(4-methoxybenzyloxy)-5-methyltetrahydrofuran-2-carbaldehyde

Guidance literature:: With Dess-Martin periodane; In dichloromethane; at 0 ℃; for 1h; Inert atmosphere;
DOI:10.1021/jo201570h

Reference yield:

: (3R,4R,5R)-4-(benzyloxy)-5-methyltetrahydro-2,3-furandiol

: 1346433-78-0
(2S,3R,4S,5R)-4-benzyloxy-3-(4-methoxybenzyloxy)-5-methyltetrahydrofuran-2-carbaldehyde

Guidance literature:: Multi-step reaction with 5 steps

1.1: potassium tert-butylate / dimethyl sulfoxide / 1 h / 0 - 20 °C / Inert atmosphere

1.2: 3 h / 0 - 20 °C / Inert atmosphere

2.1: 1H-imidazole / dichloromethane / 0 °C / Inert atmosphere

3.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 - 20 °C / Inert atmosphere

3.2: 20 °C / Inert atmosphere

4.1: camphor-10-sulfonic acid / methanol / 4 h / 0 - 20 °C

5.1: Dess-Martin periodane / dichloromethane / 1 h / 0 °C / Inert atmosphere

With 1H-imidazole; camphor-10-sulfonic acid; potassium tert-butylate; sodium hydride; Dess-Martin periodane; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; mineral oil;
DOI:10.1021/jo201570h

Reference yield:

: 1346433-75-7
(3S,4R,5R)-4-benzyloxy-2-(hydroxymethyl)-5-methyltetrahydrofuran-3-ol

: 1346433-78-0
(2S,3R,4S,5R)-4-benzyloxy-3-(4-methoxybenzyloxy)-5-methyltetrahydrofuran-2-carbaldehyde

Guidance literature:: Multi-step reaction with 4 steps

1.1: 1H-imidazole / dichloromethane / 0 °C / Inert atmosphere

2.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 - 20 °C / Inert atmosphere

2.2: 20 °C / Inert atmosphere

3.1: camphor-10-sulfonic acid / methanol / 4 h / 0 - 20 °C

4.1: Dess-Martin periodane / dichloromethane / 1 h / 0 °C / Inert atmosphere

With 1H-imidazole; camphor-10-sulfonic acid; sodium hydride; Dess-Martin periodane; In tetrahydrofuran; methanol; dichloromethane; mineral oil;
DOI:10.1021/jo201570h