5'-epiequisetin

Base Information

• Chemical Name: 5'-epiequisetin
• CAS No.: 255377-45-8
• Molecular Formula: C₂₂H₃₁NO₄
• Molecular Weight: 373.492
• Mol file: 255377-45-8.mol

Synonyms:

Chemical Property of 5'-epiequisetin

Chemical Property:

Purity/Quality:

>98% by HPLC ^*data from raw suppliers

Epiequisetin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Epiequisetin is a minor isomer of equisetin, a potent inhibitor of HIV-integrase produced by a number of species of Fusarium. Chemically, equisetin equilibrates with epiequisetin. Although found to have comparable phytotoxicity to equisetin, epiequisetin has not been extensively investigated. Epiequisetin is a phytotoxic isomer of equisetin and inhibitor of HIV-integrase.

Technology Process of 5'-epiequisetin

There total 24 articles about 5'-epiequisetin 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:

(R)-Citronellal (2385-77-5) → 5'-epiequisetin (255377-45-8)

Guidance literature:

Multi-step reaction with 23 steps

2: 86 percent / chromous chloride; LiI / tetrahydrofuran

3: 87 percent / Ph₃P; NaOH / Pd₂((dba)2*CHCl₃ / tetrahydrofuran; H₂O / Heating

4: 99 percent / DIBAL-H / tetrahydrofuran / -78 °C

5: 94 percent / i-Pr₂NEt; 4-DMAP / CH₂Cl₂

6: 98 percent / n-Bu₄NF / tetrahydrofuran

7: 91 percent / CH₂Cl₂ / -78 °C

8: 99 percent / benzene / Heating

9: 94 percent / DIBAL-H / tetrahydrofuran / -78 °C

10: 93 percent / CH₂Cl₂ / -78 °C

11: 75 percent / Me₃Al / CH₂Cl₂ / 4 h / 0 °C

12: NaBH₄ / ethanol / 0 °C

13: 92 percent / imidazole; 4-DMAP / CH₂Cl₂

14: 62 percent / bromotrimethylsilane / CH₂Cl₂

15: 95 percent / CH₂Cl₂

16: 93 percent / chromous chloride / tetrahydrofuran / 20 °C

17: 99 percent / n-Bu₄NF / dimethylformamide

18: 99 percent / CH₂Cl₂

19: 92 percent / Zn / benzene / Heating

20: 83 percent / Dess-Martin periodinane / CH₂Cl₂

21: 96 percent / toluene / Heating

22: 99 percent / HF / acetonitrile

23: NaH / CH₂Cl₂

With 1H-imidazole; chromium dichloride; dmap; sodium hydroxide; sodium tetrahydroborate; trimethylsilyl bromide; hydrogen fluoride; tetrabutyl ammonium fluoride; trimethylaluminum; sodium hydride; diisobutylaluminium hydride; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; triphenylphosphine; lithium iodide; zinc; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; In tetrahydrofuran; ethanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile; benzene; 3: Suzuki coupling / 7: Swern oxidation / 8: Wittig reaction / 10: Swern oxidation / 11: intramolecular Diels-Alder reaction / 15: Dess-Martin oxidation / 18: Swern oxidation / 19: Reformatsky reaction / 20: Dess-Martin oxidation;

DOI:10.1016/S0040-4039(01)00217-9

Reference yield:

(R)-6-(tert-Butyl-diphenyl-silanyloxy)-3-methyl-hexanal (342374-96-3) → 5'-epiequisetin (255377-45-8)

Guidance literature:

Multi-step reaction with 22 steps

1: 86 percent / chromous chloride; LiI / tetrahydrofuran

2: 87 percent / Ph₃P; NaOH / Pd₂((dba)2*CHCl₃ / tetrahydrofuran; H₂O / Heating

3: 99 percent / DIBAL-H / tetrahydrofuran / -78 °C

4: 94 percent / i-Pr₂NEt; 4-DMAP / CH₂Cl₂

5: 98 percent / n-Bu₄NF / tetrahydrofuran

6: 91 percent / CH₂Cl₂ / -78 °C

7: 99 percent / benzene / Heating

8: 94 percent / DIBAL-H / tetrahydrofuran / -78 °C

9: 93 percent / CH₂Cl₂ / -78 °C

10: 75 percent / Me₃Al / CH₂Cl₂ / 4 h / 0 °C

11: NaBH₄ / ethanol / 0 °C

12: 92 percent / imidazole; 4-DMAP / CH₂Cl₂

13: 62 percent / bromotrimethylsilane / CH₂Cl₂

14: 95 percent / CH₂Cl₂

15: 93 percent / chromous chloride / tetrahydrofuran / 20 °C

16: 99 percent / n-Bu₄NF / dimethylformamide

17: 99 percent / CH₂Cl₂

18: 92 percent / Zn / benzene / Heating

19: 83 percent / Dess-Martin periodinane / CH₂Cl₂

20: 96 percent / toluene / Heating

21: 99 percent / HF / acetonitrile

22: NaH / CH₂Cl₂

With 1H-imidazole; chromium dichloride; dmap; sodium hydroxide; sodium tetrahydroborate; trimethylsilyl bromide; hydrogen fluoride; tetrabutyl ammonium fluoride; trimethylaluminum; sodium hydride; diisobutylaluminium hydride; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; triphenylphosphine; lithium iodide; zinc; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; In tetrahydrofuran; ethanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile; benzene; 2: Suzuki coupling / 6: Swern oxidation / 7: Wittig reaction / 9: Swern oxidation / 10: intramolecular Diels-Alder reaction / 14: Dess-Martin oxidation / 17: Swern oxidation / 18: Reformatsky reaction / 19: Dess-Martin oxidation;

DOI:10.1016/S0040-4039(01)00217-9

Reference yield:

C30H47BO3Si → 5'-epiequisetin (255377-45-8)

Guidance literature:

Multi-step reaction with 21 steps

1: 87 percent / Ph₃P; NaOH / Pd₂((dba)2*CHCl₃ / tetrahydrofuran; H₂O / Heating

2: 99 percent / DIBAL-H / tetrahydrofuran / -78 °C

3: 94 percent / i-Pr₂NEt; 4-DMAP / CH₂Cl₂

4: 98 percent / n-Bu₄NF / tetrahydrofuran

5: 91 percent / CH₂Cl₂ / -78 °C

6: 99 percent / benzene / Heating

7: 94 percent / DIBAL-H / tetrahydrofuran / -78 °C

8: 93 percent / CH₂Cl₂ / -78 °C

9: 75 percent / Me₃Al / CH₂Cl₂ / 4 h / 0 °C

10: NaBH₄ / ethanol / 0 °C

11: 92 percent / imidazole; 4-DMAP / CH₂Cl₂

12: 62 percent / bromotrimethylsilane / CH₂Cl₂

13: 95 percent / CH₂Cl₂

14: 93 percent / chromous chloride / tetrahydrofuran / 20 °C

15: 99 percent / n-Bu₄NF / dimethylformamide

16: 99 percent / CH₂Cl₂

17: 92 percent / Zn / benzene / Heating

18: 83 percent / Dess-Martin periodinane / CH₂Cl₂

19: 96 percent / toluene / Heating

20: 99 percent / HF / acetonitrile

21: NaH / CH₂Cl₂

With 1H-imidazole; chromium dichloride; dmap; sodium hydroxide; sodium tetrahydroborate; trimethylsilyl bromide; hydrogen fluoride; tetrabutyl ammonium fluoride; trimethylaluminum; sodium hydride; diisobutylaluminium hydride; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; triphenylphosphine; zinc; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; In tetrahydrofuran; ethanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile; benzene; 1: Suzuki coupling / 5: Swern oxidation / 6: Wittig reaction / 8: Swern oxidation / 9: intramolecular Diels-Alder reaction / 13: Dess-Martin oxidation / 16: Swern oxidation / 17: Reformatsky reaction / 18: Dess-Martin oxidation;

DOI:10.1016/S0040-4039(01)00217-9

upstream raw materials:

(-)-equisetin

(R)-Citronellal

[(1S,2R,4aS,6R,8aR)-1,6-Dimethyl-2-((E)-propenyl)-1,2,4a,5,6,7,8,8a-octahydro-naphthalen-1-yl]-methanol

(1S,2R,4aS,6R,8aR)-1,6-dimethyl-2-[(1E)-prop-1-en-1-yl]-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-carbaldehyde

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