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

Base Information

• Chemical Name: N-Cbz-D-Ser[N-Me-Boc-Val]-(S)-β-L-hydroxy-Pip-Gly-Sar allyl ester
• CAS No.: 1515605-80-7
• Molecular Formula: C₃₆H₅₃N₅O₁₂
• Molecular Weight: 747.843
• Mol file: 1515605-80-7.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 16 articles about N-Cbz-D-Ser[N-Me-Boc-Val]-(S)-β-L-hydroxy-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: 87.0%

N-Cbz-D-Ser[N-Me-Boc-Val]-(S)-β-L-triisopropylsilyloxy-Pip-Gly-Sar allyl ester (1515605-42-1) → N-Cbz-D-Ser[N-Me-Boc-Val]-(S)-β-L-hydroxy-Pip-Gly-Sar allyl ester (1515605-80-7)

Guidance literature:

With triethylamine tris(hydrogen fluoride); In acetonitrile; at 50 ℃; for 19h; Inert atmosphere;

DOI:10.1021/ol403319m

Reference yield:

(S)-5-azido-2-triisopropylsilyloxy-1-pentanol (1515605-77-2) → N-Cbz-D-Ser[N-Me-Boc-Val]-(S)-β-L-hydroxy-Pip-Gly-Sar allyl ester (1515605-80-7)

Guidance literature:

Multi-step reaction with 4 steps

1: triethylamine; sulfur trioxide pyridine complex; dimethyl sulfoxide / 0.5 h / 20 °C / Inert atmosphere

2: triethylphosphine / toluene; tetrahydrofuran / 30 h / 0 - 20 °C / Inert atmosphere

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

4: triethylamine tris(hydrogen fluoride) / acetonitrile / 19 h / 50 °C / Inert atmosphere

With sulfur trioxide pyridine complex; dimethyl sulfoxide; triethylamine tris(hydrogen fluoride); triethylamine; triethylphosphine; In tetrahydrofuran; toluene; acetonitrile; 3: |Ugi Condensation;

DOI:10.1021/ol403319m

Reference yield:

Glycylsarcosine (29816-01-1) → N-Cbz-D-Ser[N-Me-Boc-Val]-(S)-β-L-hydroxy-Pip-Gly-Sar allyl ester (1515605-80-7)

Guidance literature:

Multi-step reaction with 7 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: triethylamine tris(hydrogen fluoride) / acetonitrile / 19 h / 50 °C / Inert atmosphere

With hydrogenchloride; dmap; bis(trichloromethyl) carbonate; acetic anhydride; sodium hydrogencarbonate; triethylamine tris(hydrogen fluoride); 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; triethylphosphine; In tetrahydrofuran; dichloromethane; water; ethyl acetate; toluene; acetonitrile; 6.1: |Ugi Condensation;

DOI:10.1021/ol403319m

upstream raw materials:

(S)-5-azido-2-triisopropylsilyloxy-1-pentanol

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

t-BuOCO-Gly-Sar-OH

Glycylsarcosine

Refernces