(2R,3S,4R,5S)-3-Benzyloxy-5-fluoro-2-methoxy-2-methyl-tetrahydro-pyran-4-ol

Base Information

Chemical Name:(2R,3S,4R,5S)-3-Benzyloxy-5-fluoro-2-methoxy-2-methyl-tetrahydro-pyran-4-ol
CAS No.:141564-94-5
Molecular Formula:C₁₄H₁₉FO₄
Molecular Weight:270.301
Hs Code.:

Synonyms:(2R,3S,4R,5S)-3-Benzyloxy-5-fluoro-2-methoxy-2-methyl-tetrahydro-pyran-4-ol

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Chemical Property of (2R,3S,4R,5S)-3-Benzyloxy-5-fluoro-2-methoxy-2-methyl-tetrahydro-pyran-4-ol

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Technology Process of (2R,3S,4R,5S)-3-Benzyloxy-5-fluoro-2-methoxy-2-methyl-tetrahydro-pyran-4-ol

There total 9 articles about (2R,3S,4R,5S)-3-Benzyloxy-5-fluoro-2-methoxy-2-methyl-tetrahydro-pyran-4-ol 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: 80.0%

: 141564-93-4
(2S,3S,5S)-3-Benzyloxy-2-bromomethyl-5-fluoro-2-methoxy-tetrahydro-pyran-4-one

: 141564-94-5
(2R,3S,4R,5S)-3-Benzyloxy-5-fluoro-2-methoxy-2-methyl-tetrahydro-pyran-4-ol

Guidance literature:: With lithium aluminium tetrahydride; In tetrahydrofuran; for 5h; -78 deg C - r.t.;

Reference yield:

: 25018-67-1
1,2;4,5-di-O-isopropylidene-β-D-(-)-fructopyranose

: 141564-94-5
(2R,3S,4R,5S)-3-Benzyloxy-5-fluoro-2-methoxy-2-methyl-tetrahydro-pyran-4-ol

Guidance literature:: Multi-step reaction with 8 steps

1: NaH / dimethylformamide / 1 h / Ambient temperature

2: 80percent aq. HOAc / H₂O / 15 h / Ambient temperature

3: 59 percent / pyridine / 15 h / 80 °C

4: 62 percent / diethylaminosulfur trifluoride (DAST), pyridine / benzene / 5 h / 60 °C

5: 80 percent / Dowex 50W (H+) / 18 h / Ambient temperature

6: 56 percent / CBr₄, Ph₃P, pyridine / 8 h / 100 °C

7: 88 percent / DMSO, dicyclohexylcarbodiimide, pyridinium trifluoroacetate / benzene / 3 h / Ambient temperature

8: 80 percent / lithium aluminium hydride / tetrahydrofuran / 5 h / -78 deg C - r.t.

With pyridine; lithium aluminium tetrahydride; carbon tetrabromide; diethylamino-sulfur trifluoride; Dowex 50W (H+); pyridinium trifluroacetate; sodium hydride; acetic acid; dimethyl sulfoxide; dicyclohexyl-carbodiimide; triphenylphosphine; In tetrahydrofuran; water; N,N-dimethyl-formamide; benzene;

Reference yield:

: 100-39-0
benzyl bromide

: 141564-94-5
(2R,3S,4R,5S)-3-Benzyloxy-5-fluoro-2-methoxy-2-methyl-tetrahydro-pyran-4-ol

Guidance literature:: Multi-step reaction with 8 steps

1: NaH / dimethylformamide / 1 h / Ambient temperature

2: 80percent aq. HOAc / H₂O / 15 h / Ambient temperature

3: 59 percent / pyridine / 15 h / 80 °C

4: 62 percent / diethylaminosulfur trifluoride (DAST), pyridine / benzene / 5 h / 60 °C

5: 80 percent / Dowex 50W (H+) / 18 h / Ambient temperature

6: 56 percent / CBr₄, Ph₃P, pyridine / 8 h / 100 °C

7: 88 percent / DMSO, dicyclohexylcarbodiimide, pyridinium trifluoroacetate / benzene / 3 h / Ambient temperature

8: 80 percent / lithium aluminium hydride / tetrahydrofuran / 5 h / -78 deg C - r.t.

With pyridine; lithium aluminium tetrahydride; carbon tetrabromide; diethylamino-sulfur trifluoride; Dowex 50W (H+); pyridinium trifluroacetate; sodium hydride; acetic acid; dimethyl sulfoxide; dicyclohexyl-carbodiimide; triphenylphosphine; In tetrahydrofuran; water; N,N-dimethyl-formamide; benzene;