Benzoic acid (2S,3R,5S)-3-hydroxy-5-methoxy-tetrahydro-furan-2-ylmethyl ester

Base Information

Chemical Name:Benzoic acid (2S,3R,5S)-3-hydroxy-5-methoxy-tetrahydro-furan-2-ylmethyl ester
CAS No.:395075-14-6
Molecular Formula:C₁₃H₁₆O₅
Molecular Weight:252.267
Hs Code.:

Synonyms:Benzoic acid (2S,3R,5S)-3-hydroxy-5-methoxy-tetrahydro-furan-2-ylmethyl ester

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Chemical Property of Benzoic acid (2S,3R,5S)-3-hydroxy-5-methoxy-tetrahydro-furan-2-ylmethyl ester

Chemical Property:

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Technology Process of Benzoic acid (2S,3R,5S)-3-hydroxy-5-methoxy-tetrahydro-furan-2-ylmethyl ester

There total 4 articles about Benzoic acid (2S,3R,5S)-3-hydroxy-5-methoxy-tetrahydro-furan-2-ylmethyl 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:

: 171721-11-2
5-O-benzoyl-1,2-O-isopropylidene-α-L-ribofuranose

: 395075-14-6
Benzoic acid (2S,3R,5S)-3-hydroxy-5-methoxy-tetrahydro-furan-2-ylmethyl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: NaH / tetrahydrofuran / 1 h / 0 - 20 °C

1.2: TBAI / tetrahydrofuran / 0 - 20 °C

2.1: aq. HCl / dioxane; methanol / 1.5 h / 20 °C

3.1: DMAP / toluene / 3 h / 90 °C

4.1: Bu₃SnH; AIBN / 1 h / Heating

5.1: 60 percent / H₂ / Pd/C / ethanol / 72 h / 20 °C / 2844.39 Torr

With hydrogenchloride; dmap; 2,2'-azobis(isobutyronitrile); hydrogen; tri-n-butyl-tin hydride; sodium hydride; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; toluene;
DOI:10.1021/ol0168059

Reference yield:

: 395075-12-4
Benzoic acid (2S,3R,4S,5S)-3-benzyloxy-4-hydroxy-5-methoxy-tetrahydro-furan-2-ylmethyl ester

: 395075-14-6
Benzoic acid (2S,3R,5S)-3-hydroxy-5-methoxy-tetrahydro-furan-2-ylmethyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: DMAP / toluene / 3 h / 90 °C

2: Bu₃SnH; AIBN / 1 h / Heating

3: 60 percent / H₂ / Pd/C / ethanol / 72 h / 20 °C / 2844.39 Torr

With dmap; 2,2'-azobis(isobutyronitrile); hydrogen; tri-n-butyl-tin hydride; palladium on activated charcoal; In ethanol; toluene;
DOI:10.1021/ol0168059

Reference yield:

: 479035-83-1
Benzoic acid (3aS,5S,6S,6aS)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-ylmethyl ester

: 395075-14-6
Benzoic acid (2S,3R,5S)-3-hydroxy-5-methoxy-tetrahydro-furan-2-ylmethyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: aq. HCl / dioxane; methanol / 1.5 h / 20 °C

2: DMAP / toluene / 3 h / 90 °C

3: Bu₃SnH; AIBN / 1 h / Heating

4: 60 percent / H₂ / Pd/C / ethanol / 72 h / 20 °C / 2844.39 Torr

With hydrogenchloride; dmap; 2,2'-azobis(isobutyronitrile); hydrogen; tri-n-butyl-tin hydride; palladium on activated charcoal; In 1,4-dioxane; methanol; ethanol; toluene;
DOI:10.1021/ol0168059