(2S,3S,4R,5R)-2-((R)-Benzyloxy-phenyl-methyl)-5-vinyl-tetrahydro-furan-3,4-diol

Base Information

Chemical Name:(2S,3S,4R,5R)-2-((R)-Benzyloxy-phenyl-methyl)-5-vinyl-tetrahydro-furan-3,4-diol
CAS No.:201863-48-1
Molecular Formula:C₂₀H₂₂O₄
Molecular Weight:326.392
Hs Code.:

Synonyms:(2S,3S,4R,5R)-2-((R)-Benzyloxy-phenyl-methyl)-5-vinyl-tetrahydro-furan-3,4-diol

Suppliers and Price of (2S,3S,4R,5R)-2-((R)-Benzyloxy-phenyl-methyl)-5-vinyl-tetrahydro-furan-3,4-diol

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (2S,3S,4R,5R)-2-((R)-Benzyloxy-phenyl-methyl)-5-vinyl-tetrahydro-furan-3,4-diol

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Technology Process of (2S,3S,4R,5R)-2-((R)-Benzyloxy-phenyl-methyl)-5-vinyl-tetrahydro-furan-3,4-diol

There total 11 articles about (2S,3S,4R,5R)-2-((R)-Benzyloxy-phenyl-methyl)-5-vinyl-tetrahydro-furan-3,4-diol 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: 86.0%

: 201863-45-8
(3aR,4R,6R,6aS)-4-((R)-Benzyloxy-phenyl-methyl)-2,2-dimethyl-6-vinyl-tetrahydro-furo[3,4-d][1,3]dioxole

: 201863-48-1
(2S,3S,4R,5R)-2-((R)-Benzyloxy-phenyl-methyl)-5-vinyl-tetrahydro-furan-3,4-diol

Guidance literature:: With sulfuric acid; In 1,4-dioxane; for 2h; Heating;

Reference yield:

: 108-86-1,52753-63-6
bromobenzene

: 201863-48-1
(2S,3S,4R,5R)-2-((R)-Benzyloxy-phenyl-methyl)-5-vinyl-tetrahydro-furan-3,4-diol

Guidance literature:: Multi-step reaction with 8 steps

1: 1.) Mg / 1.) THF, 2.) 0 deg C, 3 h

2: 79 percent / PDC, 4 Angstroem molecular sieves / CH₂Cl₂ / 3 h / 50 °C

3: 80 percent / NaBH₄ / methanol / 0.5 h / -10 °C

4: 86 percent / NaH / dimethylformamide / 1 h / Ambient temperature

5: 85 percent / 60percent aq. AcOH / 8 h / Ambient temperature

6: 84 percent / TEA / CH₂Cl₂ / 0.5 h / 0 °C

7: 81 percent / NaI / butan-2-one / 8 h / Heating

8: 86 percent / aq.H₂SO₄ / dioxane / 2 h / Heating

With sodium tetrahydroborate; dipyridinium dichromate; 4 A molecular sieve; TEA; sulfuric acid; sodium hydride; magnesium; acetic acid; sodium iodide; In 1,4-dioxane; methanol; dichloromethane; N,N-dimethyl-formamide; butanone;

Reference yield:

: 7757-38-2,14131-84-1,23262-78-4,27108-13-0,33823-04-0,34685-42-2,57819-52-0,78039-08-4,78039-12-0,78964-16-6,94842-76-9,149342-31-4
2,3,5,6-di-O-isopropylidene-D-mannofuranose

: 201863-48-1
(2S,3S,4R,5R)-2-((R)-Benzyloxy-phenyl-methyl)-5-vinyl-tetrahydro-furan-3,4-diol

Guidance literature:: Multi-step reaction with 10 steps

1: 1.) t-BuOK / 1.) DMSO, 10 deg C, 30 min, 2.) DMSO, r.t., 30 min

2: 1.) oxalyl dichloride, DMSO, 2.) TEA / 1.) CH₂Cl₂, - 78 deg C, 45 min, 2.) -78 deg C to r.t.

3: 1.) Mg / 1.) THF, 2.) 0 deg C, 3 h

4: 79 percent / PDC, 4 Angstroem molecular sieves / CH₂Cl₂ / 3 h / 50 °C

5: 80 percent / NaBH₄ / methanol / 0.5 h / -10 °C

6: 86 percent / NaH / dimethylformamide / 1 h / Ambient temperature

7: 85 percent / 60percent aq. AcOH / 8 h / Ambient temperature

8: 84 percent / TEA / CH₂Cl₂ / 0.5 h / 0 °C

9: 81 percent / NaI / butan-2-one / 8 h / Heating

10: 86 percent / aq.H₂SO₄ / dioxane / 2 h / Heating

With sodium tetrahydroborate; dipyridinium dichromate; oxalyl dichloride; 4 A molecular sieve; TEA; sulfuric acid; potassium tert-butylate; sodium hydride; magnesium; acetic acid; dimethyl sulfoxide; sodium iodide; In 1,4-dioxane; methanol; dichloromethane; N,N-dimethyl-formamide; butanone;