(R)-2-[(2S,3R,5R)-3-(2-Benzyloxy-ethyl)-5-methyl-6-oxo-tetrahydro-pyran-2-yl]-propionic acid

Base Information

Chemical Name:(R)-2-[(2S,3R,5R)-3-(2-Benzyloxy-ethyl)-5-methyl-6-oxo-tetrahydro-pyran-2-yl]-propionic acid
CAS No.:83005-65-6
Molecular Formula:C₁₈H₂₄O₅
Molecular Weight:320.386
Hs Code.:

Synonyms:(R)-2-[(2S,3R,5R)-3-(2-Benzyloxy-ethyl)-5-methyl-6-oxo-tetrahydro-pyran-2-yl]-propionic acid

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Chemical Property of (R)-2-[(2S,3R,5R)-3-(2-Benzyloxy-ethyl)-5-methyl-6-oxo-tetrahydro-pyran-2-yl]-propionic acid

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Technology Process of (R)-2-[(2S,3R,5R)-3-(2-Benzyloxy-ethyl)-5-methyl-6-oxo-tetrahydro-pyran-2-yl]-propionic acid

There total 9 articles about (R)-2-[(2S,3R,5R)-3-(2-Benzyloxy-ethyl)-5-methyl-6-oxo-tetrahydro-pyran-2-yl]-propionic acid 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:

: 10385-30-5
4-(benzyloxy)butanoic acid

: 83005-65-6
(R)-2-[(2S,3R,5R)-3-(2-Benzyloxy-ethyl)-5-methyl-6-oxo-tetrahydro-pyran-2-yl]-propionic acid

Guidance literature:: Multi-step reaction with 9 steps

1: 82 percent / lithium diisopropylamide, hexamethylphosphoramide / tetrahydrofuran; hexane / 1.5 h / 0 deg C -> room temperature

2: 98 percent / lithium aluminium hydride / tetrahydrofuran / 0.75 h / 0 deg C -> room temperature

3: 87 percent / CrO₃*2C₅H₅N / CH₂Cl₂ / 0.25 h / 0 °C

4: CH₂Cl₂ / 17 h / Ambient temperature

5: 100 percent / 2,6-lutidine / CH₂Cl₂ / 0.33 h / -10 deg C -> 0 deg C

6: 1.) (-)-bis(isopinocamphenyl)borane, 2.) m-chloroperoxybenzoic acid / 1.) THF, room temperature, 30 min, 2.) 0 deg C, 1 h

7: 70percent aq. HOAc / tetrahydrofuran / 3 h / 55 °C

8: 70 percent / Ag₂CO₃ on Celite / benzene / 0.75 h / Heating

9: 1.) conc. HF, 2.) NaIO₄ / 1.) CH₃CN, room temperature, 4 h, 2.) MeOH, H₂O, room temperature, 2.5 h

With 2,6-dimethylpyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium periodate; lithium aluminium tetrahydride; hydrogen fluoride; dipyridine chromium trioxide; acetic acid; 3-chloro-benzenecarboperoxoic acid; diisopinocampheylborane; silver carbonate; lithium diisopropyl amide; In tetrahydrofuran; hexane; dichloromethane; benzene;
DOI:10.1021/ja00384a061

Reference yield:

: 83005-57-6,83005-58-7
2-(2-Benzyloxy-ethyl)-4-methyl-pent-4-enal

: 83005-65-6
(R)-2-[(2S,3R,5R)-3-(2-Benzyloxy-ethyl)-5-methyl-6-oxo-tetrahydro-pyran-2-yl]-propionic acid

Guidance literature:: Multi-step reaction with 6 steps

1: CH₂Cl₂ / 17 h / Ambient temperature

2: 100 percent / 2,6-lutidine / CH₂Cl₂ / 0.33 h / -10 deg C -> 0 deg C

3: 1.) (-)-bis(isopinocamphenyl)borane, 2.) m-chloroperoxybenzoic acid / 1.) THF, room temperature, 30 min, 2.) 0 deg C, 1 h

4: 70percent aq. HOAc / tetrahydrofuran / 3 h / 55 °C

5: 70 percent / Ag₂CO₃ on Celite / benzene / 0.75 h / Heating

6: 1.) conc. HF, 2.) NaIO₄ / 1.) CH₃CN, room temperature, 4 h, 2.) MeOH, H₂O, room temperature, 2.5 h

With 2,6-dimethylpyridine; sodium periodate; hydrogen fluoride; acetic acid; 3-chloro-benzenecarboperoxoic acid; diisopinocampheylborane; silver carbonate; In tetrahydrofuran; dichloromethane; benzene;
DOI:10.1021/ja00384a061

Reference yield:

: 83005-55-4
2-(2-Benzyloxy-ethyl)-4-methyl-pent-4-enoic acid

: 83005-65-6
(R)-2-[(2S,3R,5R)-3-(2-Benzyloxy-ethyl)-5-methyl-6-oxo-tetrahydro-pyran-2-yl]-propionic acid

Guidance literature:: Multi-step reaction with 8 steps

1: 98 percent / lithium aluminium hydride / tetrahydrofuran / 0.75 h / 0 deg C -> room temperature

2: 87 percent / CrO₃*2C₅H₅N / CH₂Cl₂ / 0.25 h / 0 °C

3: CH₂Cl₂ / 17 h / Ambient temperature

4: 100 percent / 2,6-lutidine / CH₂Cl₂ / 0.33 h / -10 deg C -> 0 deg C

5: 1.) (-)-bis(isopinocamphenyl)borane, 2.) m-chloroperoxybenzoic acid / 1.) THF, room temperature, 30 min, 2.) 0 deg C, 1 h

6: 70percent aq. HOAc / tetrahydrofuran / 3 h / 55 °C

7: 70 percent / Ag₂CO₃ on Celite / benzene / 0.75 h / Heating

8: 1.) conc. HF, 2.) NaIO₄ / 1.) CH₃CN, room temperature, 4 h, 2.) MeOH, H₂O, room temperature, 2.5 h

With 2,6-dimethylpyridine; sodium periodate; lithium aluminium tetrahydride; hydrogen fluoride; dipyridine chromium trioxide; acetic acid; 3-chloro-benzenecarboperoxoic acid; diisopinocampheylborane; silver carbonate; In tetrahydrofuran; dichloromethane; benzene;
DOI:10.1021/ja00384a061