N-Cbz-D-Ser[N-Cbz-D-Ser(N-Me-Boc-L-Val)-L-Pip-Gly-Sar-N-Me-L-Val]-L-Pip-Gly-Sar allyl ester

Base Information

Chemical Name:N-Cbz-D-Ser[N-Cbz-D-Ser(N-Me-Boc-L-Val)-L-Pip-Gly-Sar-N-Me-L-Val]-L-Pip-Gly-Sar allyl ester
CAS No.:1515605-92-1
Molecular Formula:C₆₄H₉₂N₁₀O₁₉
Molecular Weight:1305.49
Hs Code.:

Synonyms:N-Cbz-D-Ser[N-Cbz-D-Ser(N-Me-Boc-L-Val)-L-Pip-Gly-Sar-N-Me-L-Val]-L-Pip-Gly-Sar allyl ester

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Chemical Property of N-Cbz-D-Ser[N-Cbz-D-Ser(N-Me-Boc-L-Val)-L-Pip-Gly-Sar-N-Me-L-Val]-L-Pip-Gly-Sar allyl ester

Chemical Property:

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Technology Process of N-Cbz-D-Ser[N-Cbz-D-Ser(N-Me-Boc-L-Val)-L-Pip-Gly-Sar-N-Me-L-Val]-L-Pip-Gly-Sar allyl ester

There total 19 articles about N-Cbz-D-Ser[N-Cbz-D-Ser(N-Me-Boc-L-Val)-L-Pip-Gly-Sar-N-Me-L-Val]-L-Pip-Gly-Sar allyl 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:

: 1515605-90-9
N-Cbz-D-Ser[N-Me-Boc-Val]-L-Pip-Gly-Sar-OH

: 1515605-87-4
C₃₁H₄₅N₅O₉*ClH

: 1515605-92-1
N-Cbz-D-Ser[N-Cbz-D-Ser(N-Me-Boc-L-Val)-L-Pip-Gly-Sar-N-Me-L-Val]-L-Pip-Gly-Sar allyl ester

Guidance literature:: With sodium hydrogencarbonate; 3-[(diethoxyphosphinyl)oxy]-1,2,3-benzotriazin-4(3H)-one; In dichloromethane; N,N-dimethyl-formamide; at 0 - 20 ℃; for 24h; Inert atmosphere;
DOI:10.1021/ol403319m

Reference yield:

: 29816-01-1
Glycylsarcosine

: 1515605-92-1
N-Cbz-D-Ser[N-Cbz-D-Ser(N-Me-Boc-L-Val)-L-Pip-Gly-Sar-N-Me-L-Val]-L-Pip-Gly-Sar allyl ester

Guidance literature:: Multi-step reaction with 10 steps

1.1: sodium hydrogencarbonate / tetrahydrofuran; water / 6 h / 0 - 20 °C

2.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / 3 h / 0 - 20 °C / Inert atmosphere

3.1: hydrogenchloride / ethyl acetate / 0.5 h / 20 °C / Inert atmosphere

4.1: acetic anhydride / 1 h / 55 °C / Inert atmosphere

4.2: 0.5 h / 0 - 20 °C / Inert atmosphere

5.1: triethylamine; bis(trichloromethyl) carbonate / dichloromethane / 0.5 h / -78 °C / Inert atmosphere

6.1: triethylphosphine / toluene / 48 h / 70 °C / Inert atmosphere

7.1: dmap; triethylamine / acetonitrile / 12 h / 20 °C / Inert atmosphere

8.1: tri-n-butyl-tin hydride; 2,2'-azobis(isobutyronitrile) / 2,2,2-trifluoroethanol / 1 h / 78 °C / Inert atmosphere

9.1: morpholine; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere

10.1: sodium hydrogencarbonate; 3-[(diethoxyphosphinyl)oxy]-1,2,3-benzotriazin-4(3H)-one / N,N-dimethyl-formamide; dichloromethane / 24 h / 0 - 20 °C / Inert atmosphere

With morpholine; hydrogenchloride; dmap; tetrakis(triphenylphosphine) palladium⁽⁰⁾; 2,2'-azobis(isobutyronitrile); bis(trichloromethyl) carbonate; tri-n-butyl-tin hydride; acetic anhydride; sodium hydrogencarbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; 3-[(diethoxyphosphinyl)oxy]-1,2,3-benzotriazin-4(3H)-one; triethylphosphine; In tetrahydrofuran; dichloromethane; 2,2,2-trifluoroethanol; water; ethyl acetate; N,N-dimethyl-formamide; toluene; acetonitrile; 6.1: |Ugi Condensation;
DOI:10.1021/ol403319m

Reference yield:

: 1515606-17-3
C₈H₁₄N₂O₃*ClH

: 1515605-92-1
N-Cbz-D-Ser[N-Cbz-D-Ser(N-Me-Boc-L-Val)-L-Pip-Gly-Sar-N-Me-L-Val]-L-Pip-Gly-Sar allyl ester

Guidance literature:: Multi-step reaction with 7 steps

1.1: acetic anhydride / 1 h / 55 °C / Inert atmosphere

1.2: 0.5 h / 0 - 20 °C / Inert atmosphere

2.1: triethylamine; bis(trichloromethyl) carbonate / dichloromethane / 0.5 h / -78 °C / Inert atmosphere

3.1: triethylphosphine / toluene / 48 h / 70 °C / Inert atmosphere

4.1: dmap; triethylamine / acetonitrile / 12 h / 20 °C / Inert atmosphere

5.1: tri-n-butyl-tin hydride; 2,2'-azobis(isobutyronitrile) / 2,2,2-trifluoroethanol / 1 h / 78 °C / Inert atmosphere

6.1: morpholine; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere

7.1: sodium hydrogencarbonate; 3-[(diethoxyphosphinyl)oxy]-1,2,3-benzotriazin-4(3H)-one / N,N-dimethyl-formamide; dichloromethane / 24 h / 0 - 20 °C / Inert atmosphere

With morpholine; dmap; tetrakis(triphenylphosphine) palladium⁽⁰⁾; 2,2'-azobis(isobutyronitrile); bis(trichloromethyl) carbonate; tri-n-butyl-tin hydride; acetic anhydride; sodium hydrogencarbonate; triethylamine; 3-[(diethoxyphosphinyl)oxy]-1,2,3-benzotriazin-4(3H)-one; triethylphosphine; In tetrahydrofuran; dichloromethane; 2,2,2-trifluoroethanol; N,N-dimethyl-formamide; toluene; acetonitrile; 3.1: |Ugi Condensation;
DOI:10.1021/ol403319m