[(S)-2-(4-Benzyloxy-phenyl)-1-((Z)-4-hydroxy-but-2-enyloxymethyl)-ethyl]-carbamic acid 9H-fluoren-9-ylmethyl ester

Base Information

• Chemical Name: [(S)-2-(4-Benzyloxy-phenyl)-1-((Z)-4-hydroxy-but-2-enyloxymethyl)-ethyl]-carbamic acid 9H-fluoren-9-ylmethyl ester
• CAS No.: 183794-26-5
• Molecular Formula: C₃₅H₃₅NO₅
• Molecular Weight: 549.667

Synonyms:[(S)-2-(4-Benzyloxy-phenyl)-1-((Z)-4-hydroxy-but-2-enyloxymethyl)-ethyl]-carbamic acid 9H-fluoren-9-ylmethyl ester

Chemical Property of [(S)-2-(4-Benzyloxy-phenyl)-1-((Z)-4-hydroxy-but-2-enyloxymethyl)-ethyl]-carbamic acid 9H-fluoren-9-ylmethyl ester

Chemical Property:

Purity/Quality:

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Technology Process of [(S)-2-(4-Benzyloxy-phenyl)-1-((Z)-4-hydroxy-but-2-enyloxymethyl)-ethyl]-carbamic acid 9H-fluoren-9-ylmethyl ester

There total 1 articles about [(S)-2-(4-Benzyloxy-phenyl)-1-((Z)-4-hydroxy-but-2-enyloxymethyl)-ethyl]-carbamic acid 9H-fluoren-9-ylmethyl 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: 92.0%

{(S)-2-(4-Benzyloxy-phenyl)-1-[(Z)-4-(tert-butyl-dimethyl-silanyloxy)-but-2-enyloxymethyl]-ethyl}-carbamic acid 9H-fluoren-9-ylmethyl ester (183794-25-4) → [(S)-2-(4-Benzyloxy-phenyl)-1-((Z)-4-hydroxy-but-2-enyloxymethyl)-ethyl]-carbamic acid 9H-fluoren-9-ylmethyl ester (183794-26-5)

Guidance literature:

With hydrogen fluoride; In acetonitrile; for 0.333333h;

DOI:10.1021/jo961114p

Reference yield: 100.0%

[(S)-2-(4-Benzyloxy-phenyl)-1-((Z)-4-hydroxy-but-2-enyloxymethyl)-ethyl]-carbamic acid 9H-fluoren-9-ylmethyl ester (183794-26-5) → [(S)-2-(4-Benzyloxy-phenyl)-1-((2S,3R)-3-hydroxymethyl-oxiranylmethoxymethyl)-ethyl]-carbamic acid 9H-fluoren-9-ylmethyl ester (183794-27-6)

Guidance literature:

With titanium(IV) isopropylate; tert.-butylhydroperoxide; D-(-)-diisopropyl tartrate; In dichloromethane; at -15 ℃; for 37h;

DOI:10.1021/jo961114p

Reference yield:

[(S)-2-(4-Benzyloxy-phenyl)-1-((Z)-4-hydroxy-but-2-enyloxymethyl)-ethyl]-carbamic acid 9H-fluoren-9-ylmethyl ester (183794-26-5) → (3S,6S,8R,12S,14S)-3-(3-Amino-propyl)-12-(4-hydroxy-benzyl)-6-(1H-indol-3-ylmethyl)-10-oxa-1,4,7-triaza-tricyclo[6.4.2.04,14]tetradecane-2,5-dione (183794-49-2)

Guidance literature:

Multi-step reaction with 16 steps

1: 100 percent / D-(-)-diisopropyl tartrate, titanium(IV) isopropoxide, t-BuOOH / CH₂Cl₂ / 37 h / -15 °C

2: 100 percent / DBU / CH₂Cl₂ / 1.5 h

3: 72 percent / dioxane / 9 h / Heating

4: 80 percent / triethylamine / CH₂Cl₂ / 1.17 h

5: 99 percent / collidine / CH₂Cl₂ / 1.25 h

6: 79 percent / triethylamine / acetonitrile / 10 h / Heating

7: 66 percent / PCl₅ / tetrahydrofuran / 1.75 h / 0 °C

8: 82 percent / Bu₄NF / tetrahydrofuran / 0.5 h

9: 94 percent / triethylamine / CH₂Cl₂ / 1.5 h / Ambient temperature

10: NaH / dimethylsulfoxide / 2 h

11: NaBH₄ / methanol

12: NaI / acetone / Heating

13: 1.) NaHCO₃ / 1.) H₂O, 2.) CH₃CN, room temp., 41 h

14: 100 percent / aq. LiOH / tetrahydrofuran / 3 h

15: 19 percent / diphenylphosphoryl azide, NaHCO₃ / dimethylformamide / 15 h / 0 °C

16: 55 percent / H₂, HOAc / Pd(OH)2/C / ethanol; H₂O; methanol / 1.67 h

With titanium(IV) isopropylate; 2,3,5-trimethyl-pyridine; tert.-butylhydroperoxide; lithium hydroxide; sodium tetrahydroborate; phosphorus pentachloride; diphenylphosphoranyl azide; tetrabutyl ammonium fluoride; hydrogen; sodium hydride; sodium hydrogencarbonate; D-(-)-diisopropyl tartrate; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; sodium iodide; palladium dihydroxide; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; acetonitrile;

DOI:10.1021/jo961114p

upstream raw materials:

{(S)-2-(4-Benzyloxy-phenyl)-1-[(Z)-4-(tert-butyl-dimethyl-silanyloxy)-but-2-enyloxymethyl]-ethyl}-carbamic acid 9H-fluoren-9-ylmethyl ester

Downstream raw materials:

[(S)-2-(4-Benzyloxy-phenyl)-1-((2S,3R)-3-hydroxymethyl-oxiranylmethoxymethyl)-ethyl]-carbamic acid 9H-fluoren-9-ylmethyl ester

{(2R,3S)-3-[(S)-2-Amino-3-(4-benzyloxy-phenyl)-propoxymethyl]-oxiranyl}-methanol

(S)-1-[(3R,5S)-5-(4-Benzyloxy-benzyl)-morpholin-3-yl]-ethane-1,2-diol

(2S,6R,7R)-2-(4-Benzyloxy-benzyl)-7-(tert-butyl-dimethyl-silanyloxy)-4-oxa-1-aza-bicyclo[4.2.0]octane

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