Biphenyl-4-carboxylic acid (2S,3R)-3-(4-hydroxy-butyl)-oxiranylmethyl ester

Base Information

Chemical Name:Biphenyl-4-carboxylic acid (2S,3R)-3-(4-hydroxy-butyl)-oxiranylmethyl ester
CAS No.:183610-96-0
Molecular Formula:C₂₀H₂₂O₄
Molecular Weight:326.392
Hs Code.:

Synonyms:Biphenyl-4-carboxylic acid (2S,3R)-3-(4-hydroxy-butyl)-oxiranylmethyl ester

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Chemical Property of Biphenyl-4-carboxylic acid (2S,3R)-3-(4-hydroxy-butyl)-oxiranylmethyl ester

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Technology Process of Biphenyl-4-carboxylic acid (2S,3R)-3-(4-hydroxy-butyl)-oxiranylmethyl ester

There total 1 articles about Biphenyl-4-carboxylic acid (2S,3R)-3-(4-hydroxy-butyl)-oxiranylmethyl 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: 67.0%

: 183610-97-1
Biphenyl-4-carboxylic acid (2S,3R)-3-[4-(tert-butyl-dimethyl-silanyloxy)-butyl]-oxiranylmethyl ester

: 183610-96-0
Biphenyl-4-carboxylic acid (2S,3R)-3-(4-hydroxy-butyl)-oxiranylmethyl ester

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 3h; Ambient temperature;
DOI:10.3987/com-97-s(n)58

Reference yield: 90.0%

: 18162-48-6
tert-butyldimethylsilyl chloride

: 183610-96-0
Biphenyl-4-carboxylic acid (2S,3R)-3-(4-hydroxy-butyl)-oxiranylmethyl ester

: 183610-97-1
Biphenyl-4-carboxylic acid (2S,3R)-3-[4-(tert-butyl-dimethyl-silanyloxy)-butyl]-oxiranylmethyl ester

Guidance literature:: With N-ethyl-N,N-diisopropylamine; In 1,2-dichloro-ethane; for 3h; Ambient temperature;
DOI:10.3987/com-97-s(n)58

Reference yield:

: 183610-96-0
Biphenyl-4-carboxylic acid (2S,3R)-3-(4-hydroxy-butyl)-oxiranylmethyl ester

: 205808-92-0
(R)-5-(tert-Butyl-diphenyl-silanyloxy)-5-((1S,2R)-2-{(E)-2-[(4R,5S)-2,2-dimethyl-5-((Z)-oct-2-enyl)-[1,3]dioxolan-4-yl]-vinyl}-cyclopropyl)-pentan-1-ol

Guidance literature:: Multi-step reaction with 15 steps

1: 90 percent / i-Pr₂NEt / 1,2-dichloro-ethane / 3 h / Ambient temperature

2: 98 percent / K₂CO₃ / methanol / 0.5 h / Ambient temperature

3: 97 percent / DMAP / CH₂Cl₂ / 2 h / 0 °C

4: 83 percent / 1.) BuLi / tetrahydrofuran / 1.) -78 deg C, 30 min.; 2.) -78 deg C -> room temp. over 5 h, then 1 h

5: 96 percent / dimethylformamide / 4 h / Ambient temperature

6: 92 percent / SmI₂, HMPA / tetrahydrofuran / 0.5 h / Ambient temperature

7: O₃, Me₂S / CH₂Cl₂; methanol / -78 deg C, then -> room temp., 2 h, then room temp., 8 h

8: K₂CO₃ / methanol / 16 h / 50 °C

9: 92 percent / NaBH₄ / methanol / 0.5 h / 0 °C

10: 99 percent / Bu₃P, pyridine / 3 h / 0 °C

11: 99 percent / m-CPBA / CH₂Cl₂ / 1 h / 0 °C

12: 80 percent / 1.) BuLi / tetrahydrofuran; hexane / 1.) -78 deg C, 1 h; 2.) -78 deg C, 1 h then -> room temp., 1 h, then room temp., 1 h

13: 70 percent / pyridine / 12 h / Ambient temperature

14: 56 percent / Na₂HPO₄, 5percent Na-Hg / methanol; tetrahydrofuran / 1 h / 0 °C

15: 85 percent / AcOH / H₂O; tetrahydrofuran / 1 h / Ambient temperature

With pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; sodium tetrahydroborate; disodium hydrogenphosphate; n-butyllithium; samarium diiodide; sodium amalgam; dimethylsulfide; tributylphosphine; potassium carbonate; ozone; acetic acid; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; hexane; dichloromethane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide;
DOI:10.3987/com-97-s(n)58