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

Base Information

Chemical Name:(2S,3R,4R,5S)-3-(benzyloxy)-4-hydroxy-5-methoxy-4-methyltetrahydrofuran-2-carbaldehyde
CAS No.:1608456-11-6
Molecular Formula:C₁₄H₁₈O₅
Molecular Weight:266.294
Hs Code.:

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

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

Chemical Property:

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

There total 8 articles about (2S,3R,4R,5S)-3-(benzyloxy)-4-hydroxy-5-methoxy-4-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: 91.0%

: 1608456-10-5
(R)-1-((2R,3R,4R,5S)-3-(benzyloxy)-4-hydroxy-5-methoxy-4-methyltetrahydrofuran-2-yl)ethane-1,2-diol

: 1608456-11-6
(2S,3R,4R,5S)-3-(benzyloxy)-4-hydroxy-5-methoxy-4-methyltetrahydrofuran-2-carbaldehyde

Guidance literature:: With sodium periodate; In water; at 0 ℃; for 0.5h;
DOI:10.1016/j.bmcl.2014.04.050

Reference yield:

: 2595-05-3
Diacetone D-glucose

: 1608456-11-6
(2S,3R,4R,5S)-3-(benzyloxy)-4-hydroxy-5-methoxy-4-methyltetrahydrofuran-2-carbaldehyde

Guidance literature:: Multi-step reaction with 8 steps

1.1: sodium hydride / mineral oil; acetonitrile / 1 h / 0 °C / Inert atmosphere

1.2: 4.5 h / 0 °C

2.1: acetic acid / water / 72 h / 20 °C

3.1: pyridine / acetonitrile / 0 - 60 °C

4.1: hydrogenchloride / 1,4-dioxane / 96 h / 20 °C

5.1: titanium tetrachloride / dichloromethane / 35 °C

6.1: dimethyl sulfoxide; trifluoroacetic anhydride / tetrahydrofuran / 0.25 h / -78 °C / Inert atmosphere

6.2: 1 h / -78 - 20 °C / Inert atmosphere

6.3: 2 h / -78 °C / Inert atmosphere

7.1: ammonia / methanol / 18 h / 20 °C

8.1: sodium periodate / water / 0.5 h / 0 °C

With pyridine; hydrogenchloride; sodium periodate; ammonia; titanium tetrachloride; sodium hydride; acetic acid; dimethyl sulfoxide; trifluoroacetic anhydride; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; acetonitrile; mineral oil; 6.3: |Grignard Reaction;
DOI:10.1016/j.bmcl.2014.04.050

Reference yield:

: 22331-21-1
1,2:5,6-di-O-isopropylidene-3-O-benzyl-α-D-allofuranose

: 1608456-11-6
(2S,3R,4R,5S)-3-(benzyloxy)-4-hydroxy-5-methoxy-4-methyltetrahydrofuran-2-carbaldehyde

Guidance literature:: Multi-step reaction with 7 steps

1.1: acetic acid / water / 72 h / 20 °C

2.1: pyridine / acetonitrile / 0 - 60 °C

3.1: hydrogenchloride / 1,4-dioxane / 96 h / 20 °C

4.1: titanium tetrachloride / dichloromethane / 35 °C

5.1: dimethyl sulfoxide; trifluoroacetic anhydride / tetrahydrofuran / 0.25 h / -78 °C / Inert atmosphere

5.2: 1 h / -78 - 20 °C / Inert atmosphere

5.3: 2 h / -78 °C / Inert atmosphere

6.1: ammonia / methanol / 18 h / 20 °C

7.1: sodium periodate / water / 0.5 h / 0 °C

With pyridine; hydrogenchloride; sodium periodate; ammonia; titanium tetrachloride; acetic acid; dimethyl sulfoxide; trifluoroacetic anhydride; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; acetonitrile; 5.3: |Grignard Reaction;
DOI:10.1016/j.bmcl.2014.04.050