(R)-4-Hydroxy-N-(3-hydroxy-5-{(Z)-4-[(4R,5S,6S)-6-(2-hydroxy-ethyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-pent-3-enyl}-phenyl)-3-methoxy-N-(2,2,2-trichloro-ethoxymethyl)-butyramide

Base Information

• Chemical Name: (R)-4-Hydroxy-N-(3-hydroxy-5-{(Z)-4-[(4R,5S,6S)-6-(2-hydroxy-ethyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-pent-3-enyl}-phenyl)-3-methoxy-N-(2,2,2-trichloro-ethoxymethyl)-butyramide
• CAS No.: 171013-69-7
• Molecular Formula: C₂₈H₄₂Cl₃NO₈
• Molecular Weight: 627.002
• Mol file: 171013-69-7.mol

Synonyms:(R)-4-Hydroxy-N-(3-hydroxy-5-{(Z)-4-[(4R,5S,6S)-6-(2-hydroxy-ethyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-pent-3-enyl}-phenyl)-3-methoxy-N-(2,2,2-trichloro-ethoxymethyl)-butyramide

Chemical Property of (R)-4-Hydroxy-N-(3-hydroxy-5-{(Z)-4-[(4R,5S,6S)-6-(2-hydroxy-ethyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-pent-3-enyl}-phenyl)-3-methoxy-N-(2,2,2-trichloro-ethoxymethyl)-butyramide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-4-Hydroxy-N-(3-hydroxy-5-{(Z)-4-[(4R,5S,6S)-6-(2-hydroxy-ethyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-pent-3-enyl}-phenyl)-3-methoxy-N-(2,2,2-trichloro-ethoxymethyl)-butyramide

There total 30 articles about (R)-4-Hydroxy-N-(3-hydroxy-5-{(Z)-4-[(4R,5S,6S)-6-(2-hydroxy-ethyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-pent-3-enyl}-phenyl)-3-methoxy-N-(2,2,2-trichloro-ethoxymethyl)-butyramide 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: 94.0%

C56H88Cl3NO8Si3 (171013-68-6) → (R)-4-Hydroxy-N-(3-hydroxy-5-{(Z)-4-[(4R,5S,6S)-6-(2-hydroxy-ethyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-pent-3-enyl}-phenyl)-3-methoxy-N-(2,2,2-trichloro-ethoxymethyl)-butyramide (171013-69-7)

Guidance literature:

With tetrabutyl ammonium fluoride;

DOI:10.1021/ja00148a034

Reference yield:

3-hydroxy-5-nitrobenzoic acid (78238-14-9) → (R)-4-Hydroxy-N-(3-hydroxy-5-{(Z)-4-[(4R,5S,6S)-6-(2-hydroxy-ethyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-pent-3-enyl}-phenyl)-3-methoxy-N-(2,2,2-trichloro-ethoxymethyl)-butyramide (171013-69-7)

Guidance literature:

Multi-step reaction with 11 steps

1: 60 percent / BH₃*THF / tetrahydrofuran / 15 h / Ambient temperature

2: 85 percent / CBr₄, Ph₃P / tetrahydrofuran / 2 h / 0 - 20 °C

3: 75 percent / dimethylformamide / 15 h / 60 °C

4: 95 percent / imidazole / dimethylformamide / 24 h / Ambient temperature

5: 100 percent / H₂ / 5percent Pd/C / methanol / 10 h

6: 1.) Me₃Al / 1.) C₆H₆, hexane, RT, 20 min, 2.) C₆H₆, hexane, RT, 21 h

7: 94 percent / imidazole / CH₂Cl₂ / 0.33 h / Ambient temperature

8: 1.) sodium bis(trimethylsilyl)amide / 1.) THF, -78 deg C 10 min, 2.) THF, -78 deg C, 10 min

9: 94 percent / Na(Hg), Na₂HPO₄, MeOH / 0.25 h / -20 °C

10: 1.) KH / 1.) THF, 0 deg C, 5 min, 2.) THF, RT, 20 min

11: 94 percent / TBAF / tetrahydrofuran / 3 h / Ambient temperature

With 1H-imidazole; methanol; disodium hydrogenphosphate; sodium amalgam; borane-THF; carbon tetrabromide; tetrabutyl ammonium fluoride; hydrogen; trimethylaluminum; sodium hexamethyldisilazane; potassium hydride; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ja961401a

Reference yield:

3-Benzenesulfonylmethyl-5-nitro-phenol (180628-76-6) → (R)-4-Hydroxy-N-(3-hydroxy-5-{(Z)-4-[(4R,5S,6S)-6-(2-hydroxy-ethyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-pent-3-enyl}-phenyl)-3-methoxy-N-(2,2,2-trichloro-ethoxymethyl)-butyramide (171013-69-7)

Guidance literature:

Multi-step reaction with 8 steps

1: 95 percent / imidazole / dimethylformamide / 24 h / Ambient temperature

2: 100 percent / H₂ / 5percent Pd/C / methanol / 10 h

3: 1.) Me₃Al / 1.) C₆H₆, hexane, RT, 20 min, 2.) C₆H₆, hexane, RT, 21 h

4: 94 percent / imidazole / CH₂Cl₂ / 0.33 h / Ambient temperature

5: 1.) sodium bis(trimethylsilyl)amide / 1.) THF, -78 deg C 10 min, 2.) THF, -78 deg C, 10 min

6: 94 percent / Na(Hg), Na₂HPO₄, MeOH / 0.25 h / -20 °C

7: 1.) KH / 1.) THF, 0 deg C, 5 min, 2.) THF, RT, 20 min

8: 94 percent / TBAF / tetrahydrofuran / 3 h / Ambient temperature

With 1H-imidazole; methanol; disodium hydrogenphosphate; sodium amalgam; tetrabutyl ammonium fluoride; hydrogen; trimethylaluminum; sodium hexamethyldisilazane; potassium hydride; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ja961401a

upstream raw materials:

C₅₆H₈₈Cl₃NO₈Si₃

3-hydroxy-5-nitrobenzoic acid

(2R,3R)-3-(tert-butyldimethylsilyloxy)-2,4-dimethylpent-4-enal

3-hydroxy-5-nitrobenzyl alcohol

Downstream raw materials:

(R)-N-(3-Hydroxy-5-{(Z)-4-[(4R,5S,6S)-2,2,5-trimethyl-6-(2-oxo-ethyl)-[1,3]dioxan-4-yl]-pent-3-enyl}-phenyl)-3-methoxy-4-oxo-N-(2,2,2-trichloro-ethoxymethyl)-butyramide