(2R,3S)-3-<(benzyloxycarbonyl)oxy>-2-fluorotetradecanoic acid

Base Information

Chemical Name:(2R,3S)-3-<(benzyloxycarbonyl)oxy>-2-fluorotetradecanoic acid
CAS No.:137432-72-5
Molecular Formula:C₂₂H₃₃FO₅
Molecular Weight:396.499
Hs Code.:

Synonyms:(2R,3S)-3-<(benzyloxycarbonyl)oxy>-2-fluorotetradecanoic acid

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Chemical Property of (2R,3S)-3-<(benzyloxycarbonyl)oxy>-2-fluorotetradecanoic acid

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Technology Process of (2R,3S)-3-<(benzyloxycarbonyl)oxy>-2-fluorotetradecanoic acid

There total 14 articles about (2R,3S)-3-<(benzyloxycarbonyl)oxy>-2-fluorotetradecanoic 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: 79.0%

: 137344-81-1
(2R,3S)-diphenylmethyl-3-<(benzyloxycarbonyl)oxy>-2-fluorotetradecanoate

: 137432-72-5
(2R,3S)-3-<(benzyloxycarbonyl)oxy>-2-fluorotetradecanoic acid

Guidance literature:: With trifluoroacetic acid; In dichloromethane; for 1h; Ambient temperature;
DOI:10.1016/S0040-4020(01)96156-3

Reference yield:

: 64526-50-7,137344-73-1
methyl 4-O-benzyl-2,3-dideoxy-α,β-D-erythro-hexopyranoside

: 137432-72-5
(2R,3S)-3-<(benzyloxycarbonyl)oxy>-2-fluorotetradecanoic acid

Guidance literature:: Multi-step reaction with 10 steps

1: 63 percent / Jones reagent / acetone / 1 h / 0 °C

2: ethyl acetate; diethyl ether / Ambient temperature

3: 0.5percent aq. H₂SO₄ / dioxane; H₂O / 3 h / 70 - 75 °C

4: 55 percent / tetrahydrofuran; hexane / 0.25 h / Ambient temperature

5: 34 percent / Et₂NSF₃ / CH₂Cl₂ / 2 h / Ambient temperature

6: 87 mg / 1 M NaOH / ethanol / 2 h / Ambient temperature

7: 71 mg / H₂ / 10percent Pd/C / acetic acid / 8 h / Ambient temperature

8: 60 mg / ethyl acetate / 1 h / Ambient temperature

9: 95 percent / DMAP / CH₂Cl₂ / 1) 30 min, 0 deg C, 2) 30 min, rt

10: 79 percent / CF₃COOH / CH₂Cl₂ / 1 h / Ambient temperature

With dmap; sodium hydroxide; jones reagent; diethylamino-sulfur trifluoride; sulfuric acid; hydrogen; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; diethyl ether; ethanol; hexane; dichloromethane; water; acetic acid; ethyl acetate; acetone;
DOI:10.1016/S0040-4020(01)96156-3

Reference yield:

: 137344-76-4,137344-77-5
methyl 4-O-benzyl-2,3-dideoxy-α,β-D-erythro-hexopyranuronate

: 137432-72-5
(2R,3S)-3-<(benzyloxycarbonyl)oxy>-2-fluorotetradecanoic acid

Guidance literature:: Multi-step reaction with 7 steps

1: 55 percent / tetrahydrofuran; hexane / 0.25 h / Ambient temperature

2: 34 percent / Et₂NSF₃ / CH₂Cl₂ / 2 h / Ambient temperature

3: 87 mg / 1 M NaOH / ethanol / 2 h / Ambient temperature

4: 71 mg / H₂ / 10percent Pd/C / acetic acid / 8 h / Ambient temperature

5: 60 mg / ethyl acetate / 1 h / Ambient temperature

6: 95 percent / DMAP / CH₂Cl₂ / 1) 30 min, 0 deg C, 2) 30 min, rt

7: 79 percent / CF₃COOH / CH₂Cl₂ / 1 h / Ambient temperature

With dmap; sodium hydroxide; diethylamino-sulfur trifluoride; hydrogen; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; ethanol; hexane; dichloromethane; acetic acid; ethyl acetate;
DOI:10.1016/S0040-4020(01)96156-3