pentafluorophenyl 2(S)-methyl-9(S)-<(benzyloxycarbonyl)amino>-3-(tert-butyloxycarbonyl)-3-aza-7,11,13-trioxatetradecanoate

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Chemical Name:pentafluorophenyl 2(S)-methyl-9(S)-<(benzyloxycarbonyl)amino>-3-(tert-butyloxycarbonyl)-3-aza-7,11,13-trioxatetradecanoate
CAS No.:111437-63-9
Molecular Formula:C₃₀H₃₇F₅N₂O₉
Molecular Weight:664.624
Hs Code.:

Synonyms:pentafluorophenyl 2(S)-methyl-9(S)-<(benzyloxycarbonyl)amino>-3-(tert-butyloxycarbonyl)-3-aza-7,11,13-trioxatetradecanoate

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Chemical Property of pentafluorophenyl 2(S)-methyl-9(S)-<(benzyloxycarbonyl)amino>-3-(tert-butyloxycarbonyl)-3-aza-7,11,13-trioxatetradecanoate

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Technology Process of pentafluorophenyl 2(S)-methyl-9(S)-<(benzyloxycarbonyl)amino>-3-(tert-butyloxycarbonyl)-3-aza-7,11,13-trioxatetradecanoate

There total 10 articles about pentafluorophenyl 2(S)-methyl-9(S)-<(benzyloxycarbonyl)amino>-3-(tert-butyloxycarbonyl)-3-aza-7,11,13-trioxatetradecanoate 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: 97.0%

: 771-61-9
2,3,4,5,6-pentafluorophenol

: (S)-2-{[3-((S)-2-Benzyloxycarbonylamino-3-methoxymethoxy-propoxy)-propyl]-tert-butoxycarbonyl-amino}-propionic acid

: 111437-63-9
pentafluorophenyl 2(S)-methyl-9(S)-<(benzyloxycarbonyl)amino>-3-(tert-butyloxycarbonyl)-3-aza-7,11,13-trioxatetradecanoate

Guidance literature:: With dicyclohexyl-carbodiimide; In ethyl acetate; at 0 ℃; for 0.5h;
DOI:10.1021/jm00397a003

Reference yield:

: 24424-99-5
di-tert-butyl dicarbonate

: 111437-63-9
pentafluorophenyl 2(S)-methyl-9(S)-<(benzyloxycarbonyl)amino>-3-(tert-butyloxycarbonyl)-3-aza-7,11,13-trioxatetradecanoate

Guidance literature:: Multi-step reaction with 3 steps

1: 72 percent / CHCl₃ / 12 h / Ambient temperature

2: 100 percent / aq. LiOH / dioxane / 2 h / Ambient temperature

3: 97 percent / dicyclohexylcarbodiimide / ethyl acetate / 0.5 h / 0 °C

With lithium hydroxide; dicyclohexyl-carbodiimide; In 1,4-dioxane; chloroform; ethyl acetate;
DOI:10.1021/jm00397a003

Reference yield:

: 1145-80-8
N-(benzyloxycarbonyl)-L-serine

: 111437-63-9
pentafluorophenyl 2(S)-methyl-9(S)-<(benzyloxycarbonyl)amino>-3-(tert-butyloxycarbonyl)-3-aza-7,11,13-trioxatetradecanoate

Guidance literature:: Multi-step reaction with 9 steps

1: 1.) NaH / 1.) DMF, 0 deg C, 5 min, room temperature, 2.5 h, 2.) 1 h

2: 82 percent / DIBAH / tetrahydrofuran; hexane / 0.33 h / 0 °C

3: 91 percent / (iPr)2NEt / CH₂Cl₂ / 1.) 0 deg C, 10 min, 2.) 0 deg C to room temperature

4: 91 percent / 9-BBN / tetrahydrofuran / 1.) 0 deg C to room temperature, 2.) room temperature, 5 h

5: 75 percent / dimethyl sulfoxide, oxalyl chloride / CH₂Cl₂ / 0.5 h

6: 1.) sodium acetate, 2.) sodium cyanoborohydride / 1.) 0 deg C, 30 min, 2.) -20 deg C to room temperature

7: 72 percent / CHCl₃ / 12 h / Ambient temperature

8: 100 percent / aq. LiOH / dioxane / 2 h / Ambient temperature

9: 97 percent / dicyclohexylcarbodiimide / ethyl acetate / 0.5 h / 0 °C

With lithium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; oxalyl dichloride; sodium acetate; sodium hydride; diisobutylaluminium hydride; sodium cyanoborohydride; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; 1,4-dioxane; hexane; dichloromethane; chloroform; ethyl acetate;
DOI:10.1021/jm00397a003