(4S,5RS)-N,N-dimethyl-4-(tert-butyloxycarbonylamino)-6-(benzyloxycarbonylamino)-5-hydroxyhexanamide

Base Information

Chemical Name:(4S,5RS)-N,N-dimethyl-4-(tert-butyloxycarbonylamino)-6-(benzyloxycarbonylamino)-5-hydroxyhexanamide
CAS No.:387338-10-5
Molecular Formula:C₂₁H₃₃N₃O₆
Molecular Weight:423.51
Hs Code.:

Synonyms:(4S,5RS)-N,N-dimethyl-4-(tert-butyloxycarbonylamino)-6-(benzyloxycarbonylamino)-5-hydroxyhexanamide

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Chemical Property of (4S,5RS)-N,N-dimethyl-4-(tert-butyloxycarbonylamino)-6-(benzyloxycarbonylamino)-5-hydroxyhexanamide

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Technology Process of (4S,5RS)-N,N-dimethyl-4-(tert-butyloxycarbonylamino)-6-(benzyloxycarbonylamino)-5-hydroxyhexanamide

There total 7 articles about (4S,5RS)-N,N-dimethyl-4-(tert-butyloxycarbonylamino)-6-(benzyloxycarbonylamino)-5-hydroxyhexanamide 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: 85.0%

: 501-53-1,94274-21-2
benzyl chloroformate

: [3-amino-1-(2-dimethylcarbamoyl-ethyl)-2-hydroxy-propyl]-carbamic acid tert-butyl ester; compound with acetic acid

: 387338-10-5
(4S,5RS)-N,N-dimethyl-4-(tert-butyloxycarbonylamino)-6-(benzyloxycarbonylamino)-5-hydroxyhexanamide

Guidance literature:: [3-amino-1-(2-dimethylcarbamoyl-ethyl)-2-hydroxy-propyl]-carbamic acid tert-butyl ester; compound with acetic acid; With sodium hydrogencarbonate; In tetrahydrofuran; water;

benzyl chloroformate; In tetrahydrofuran; water; at 20 ℃; Further stages.;
DOI:10.1021/jo0157831

Reference yield:

: 72468-46-3
N²-(tert-butyloxycarbonyl)-N⁵,N⁵-dimethylglutamine benzyl ester

: 387338-10-5
(4S,5RS)-N,N-dimethyl-4-(tert-butyloxycarbonylamino)-6-(benzyloxycarbonylamino)-5-hydroxyhexanamide

Guidance literature:: Multi-step reaction with 6 steps

1.1: 90 percent / H₂ / 10percent Pd/C / methanol / 6 h

2.1: ClCOOEt₃; Et₃N / CH₂Cl₂ / 0.25 h / 0 °C

2.2: 78 percent / DMAP / CH₂Cl₂ / 2 h / 0 °C

3.1: 91 percent / triethylsilane / 10percent Pd/C / dimethylformamide / 2 h / 0 °C

4.1: 70 percent / AcOH / methanol / 18 h / 20 °C

5.1: 43 percent / H₂ / PtO₂ / propan-2-ol / 24 h / 2585.81 Torr

6.1: NaHCO₃ / H₂O; tetrahydrofuran

6.2: 85 percent / H₂O; tetrahydrofuran / 20 °C

With triethylsilane; hydrogen; sodium hydrogencarbonate; acetic acid; triethylamine; platinum(IV) oxide; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; isopropyl alcohol;
DOI:10.1021/jo0157831

Reference yield:

: 30924-93-7
Boc-Glu-OBn

: 387338-10-5
(4S,5RS)-N,N-dimethyl-4-(tert-butyloxycarbonylamino)-6-(benzyloxycarbonylamino)-5-hydroxyhexanamide

Guidance literature:: Multi-step reaction with 7 steps

1.1: ClCOOEt; Et₃N / CH₂Cl₂ / 0.08 h / 0 °C

1.2: 85 percent / Et₃N / CH₂Cl₂

2.1: 90 percent / H₂ / 10percent Pd/C / methanol / 6 h

3.1: ClCOOEt₃; Et₃N / CH₂Cl₂ / 0.25 h / 0 °C

3.2: 78 percent / DMAP / CH₂Cl₂ / 2 h / 0 °C

4.1: 91 percent / triethylsilane / 10percent Pd/C / dimethylformamide / 2 h / 0 °C

5.1: 70 percent / AcOH / methanol / 18 h / 20 °C

6.1: 43 percent / H₂ / PtO₂ / propan-2-ol / 24 h / 2585.81 Torr

7.1: NaHCO₃ / H₂O; tetrahydrofuran

7.2: 85 percent / H₂O; tetrahydrofuran / 20 °C

With triethylsilane; hydrogen; chloroformic acid ethyl ester; sodium hydrogencarbonate; acetic acid; triethylamine; platinum(IV) oxide; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; isopropyl alcohol;
DOI:10.1021/jo0157831