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

Base Information

Chemical Name:methyl 2(S)-methyl-9(S)-<(benzyloxycarbonyl)amino>-3-(tert-butyloxycarbonyl)-3-aza-7,11,13-trioxatetradecanoate
CAS No.:111437-62-8
Molecular Formula:C₂₅H₄₀N₂O₉
Molecular Weight:512.601
Hs Code.:

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

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

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

There total 7 articles about methyl 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: 72.0%

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

: 111437-61-7
methyl 2(S)-methyl-9(S)-<(benzyloxycarbonyl)amino>-3-aza-7,11,13-trioxatetradecanoate

: 111437-62-8
methyl 2(S)-methyl-9(S)-<(benzyloxycarbonyl)amino>-3-(tert-butyloxycarbonyl)-3-aza-7,11,13-trioxatetradecanoate

Guidance literature:: In chloroform; for 12h; Ambient temperature;
DOI:10.1021/jm00397a003

Reference yield:

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

: 111437-62-8
methyl 2(S)-methyl-9(S)-<(benzyloxycarbonyl)amino>-3-(tert-butyloxycarbonyl)-3-aza-7,11,13-trioxatetradecanoate

Guidance literature:: Multi-step reaction with 7 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

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

Reference yield:

: 111437-57-1
N-(benzyloxycarbonyl)-O-allyl-L-serinol

: 111437-62-8
methyl 2(S)-methyl-9(S)-<(benzyloxycarbonyl)amino>-3-(tert-butyloxycarbonyl)-3-aza-7,11,13-trioxatetradecanoate

Guidance literature:: Multi-step reaction with 5 steps

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

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

3: 75 percent / dimethyl sulfoxide, oxalyl chloride / CH₂Cl₂ / 0.5 h

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

5: 72 percent / CHCl₃ / 12 h / Ambient temperature

With 9-borabicyclo[3.3.1]nonane dimer; oxalyl dichloride; sodium acetate; sodium cyanoborohydride; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; chloroform;
DOI:10.1021/jm00397a003