Benzoic acid (2R,3S,4R)-4-hydroxy-2-(2-hydroxy-ethyl)-5-methoxy-tetrahydro-furan-3-ylmethyl ester

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Chemical Name:Benzoic acid (2R,3S,4R)-4-hydroxy-2-(2-hydroxy-ethyl)-5-methoxy-tetrahydro-furan-3-ylmethyl ester
CAS No.:441044-21-9
Molecular Formula:C₁₅H₂₀O₆
Molecular Weight:296.32
Hs Code.:

Synonyms:Benzoic acid (2R,3S,4R)-4-hydroxy-2-(2-hydroxy-ethyl)-5-methoxy-tetrahydro-furan-3-ylmethyl ester

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Chemical Property of Benzoic acid (2R,3S,4R)-4-hydroxy-2-(2-hydroxy-ethyl)-5-methoxy-tetrahydro-furan-3-ylmethyl ester

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Technology Process of Benzoic acid (2R,3S,4R)-4-hydroxy-2-(2-hydroxy-ethyl)-5-methoxy-tetrahydro-furan-3-ylmethyl ester

There total 7 articles about Benzoic acid (2R,3S,4R)-4-hydroxy-2-(2-hydroxy-ethyl)-5-methoxy-tetrahydro-furan-3-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:

: 69832-48-0
((3aR,5S,6R,6aR)-tetrahydro-2,2-dimethyl-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)furo[2,3-d][1,3]dioxol-6-yl)methanol

: 441044-21-9
Benzoic acid (2R,3S,4R)-4-hydroxy-2-(2-hydroxy-ethyl)-5-methoxy-tetrahydro-furan-3-ylmethyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: pyridine / DMAP / 23 h / Ambient temperature

2: 1.6percent H₂SO₄ / methanol; CHCl₃ / 84 h

3: pyridine / 2 h / Ambient temperature

4: NaI / butan-2-one / 15 h / Heating

5: 1) BH₃*Me₂S, 2) NaHCO₃, 30percent H₂O₂ / 1a) THF, 0-4 deg C, 24 h, b) THF, methanol, 0 deg C, 1 h, 2) THF, methanol, water, up to r. t., 2 h

6: acidic cation-exchange resin (Dowex 50 W₈) / methanol / 5.5 h / Heating

With pyridine; dimethylsulfide borane complex; acidic cation-exchange resin (Dowex 50 W₈); sulfuric acid; dihydrogen peroxide; sodium hydrogencarbonate; sodium iodide; dmap; In methanol; chloroform; butanone;
DOI:10.1021/jo00012a018

Reference yield:

: 98-88-4
benzoyl chloride

: 441044-21-9
Benzoic acid (2R,3S,4R)-4-hydroxy-2-(2-hydroxy-ethyl)-5-methoxy-tetrahydro-furan-3-ylmethyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: pyridine / DMAP / 23 h / Ambient temperature

2: 1.6percent H₂SO₄ / methanol; CHCl₃ / 84 h

3: pyridine / 2 h / Ambient temperature

4: NaI / butan-2-one / 15 h / Heating

5: 1) BH₃*Me₂S, 2) NaHCO₃, 30percent H₂O₂ / 1a) THF, 0-4 deg C, 24 h, b) THF, methanol, 0 deg C, 1 h, 2) THF, methanol, water, up to r. t., 2 h

6: acidic cation-exchange resin (Dowex 50 W₈) / methanol / 5.5 h / Heating

With pyridine; dimethylsulfide borane complex; acidic cation-exchange resin (Dowex 50 W₈); sulfuric acid; dihydrogen peroxide; sodium hydrogencarbonate; sodium iodide; dmap; In methanol; chloroform; butanone;
DOI:10.1021/jo00012a018

Reference yield:

: 130495-83-9
3-deoxy-3-<(benzoyloxy)methyl>-1,2-O-isopropylidene-α-D-allofuranose

: 441044-21-9
Benzoic acid (2R,3S,4R)-4-hydroxy-2-(2-hydroxy-ethyl)-5-methoxy-tetrahydro-furan-3-ylmethyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: pyridine / 2 h / Ambient temperature

2: NaI / butan-2-one / 15 h / Heating

3: 1) BH₃*Me₂S, 2) NaHCO₃, 30percent H₂O₂ / 1a) THF, 0-4 deg C, 24 h, b) THF, methanol, 0 deg C, 1 h, 2) THF, methanol, water, up to r. t., 2 h

4: acidic cation-exchange resin (Dowex 50 W₈) / methanol / 5.5 h / Heating

With pyridine; dimethylsulfide borane complex; acidic cation-exchange resin (Dowex 50 W₈); dihydrogen peroxide; sodium hydrogencarbonate; sodium iodide; In methanol; butanone;
DOI:10.1021/jo00012a018