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

Base Information

• Chemical Name: N-Cbz-D-Ser[N-Me-Boc-Val]-(S)-β-L-triisopropylsilyloxy-Pip-Gly-Sar allyl ester
• CAS No.: 1515605-42-1
• Molecular Formula: C₄₅H₇₃N₅O₁₂Si
• Molecular Weight: 904.186

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

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

Chemical Property:

Purity/Quality:

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

There total 17 articles about N-Cbz-D-Ser[N-Me-Boc-Val]-(S)-β-L-triisopropylsilyloxy-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: 59.0%

2-propenyl 2-(2-isocyano-N-methylacetamido)acetate (1515605-46-5) + C14H29NOSi (1515605-49-8) + N-Cbz-D-Ser(N-Boc-N-Me-Val)-OH (1515605-47-6) → N-Cbz-D-Ser[N-Me-Boc-Val]-(S)-β-L-triisopropylsilyloxy-Pip-Gly-Sar allyl ester (1515605-42-1) + C45H73N5O12Si (1515606-22-0)

Guidance literature:

With triethylphosphine; In toluene; at 70 ℃; for 48h; Overall yield = 68 %; Overall yield = 550 mg; diastereoselective reaction; Inert atmosphere;

DOI:10.1021/ol403319m

Reference yield:

triisopropylsilyl trifluoromethanesulfonate (80522-42-5) → N-Cbz-D-Ser[N-Me-Boc-Val]-(S)-β-L-triisopropylsilyloxy-Pip-Gly-Sar allyl ester (1515605-42-1) + C45H73N5O12Si (1515606-22-0)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 2,6-dimethylpyridine / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere

2.1: borane-THF / tetrahydrofuran / 4 h / 0 - 20 °C / Inert atmosphere

2.2: 12 h / 0 - 20 °C

3.1: triethylamine; trimethylamine hydrochloride / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere

4.1: tetra-(n-butyl)ammonium iodide; sodium azide / N,N-dimethyl-formamide / 12 h / 0 - 20 °C / Inert atmosphere

5.1: zinc dibromide / methanol; dichloromethane / 30 h / 0 - 20 °C / Inert atmosphere

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

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

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

With 2,6-dimethylpyridine; sodium azide; borane-THF; sulfur trioxide pyridine complex; trimethylamine hydrochloride; tetra-(n-butyl)ammonium iodide; dimethyl sulfoxide; triethylamine; zinc dibromide; triethylphosphine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene; 8.1: |Ugi Condensation;

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-triisopropylsilyloxy-Pip-Gly-Sar allyl ester (1515605-42-1) + C45H73N5O12Si (1515606-22-0)

Guidance literature:

Multi-step reaction with 3 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

With sulfur trioxide pyridine complex; dimethyl sulfoxide; triethylamine; triethylphosphine; In tetrahydrofuran; toluene; 3: |Ugi Condensation;

DOI:10.1021/ol403319m

upstream raw materials:

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

t-BuOCO-Gly-Sar-OH

Glycylsarcosine

N-Boc-Gly-Sar allyl ester

Downstream raw materials:

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

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

N-Cbz-D-Ser[N-Me-Boc-Val]-L-Pip-Gly-Sar-OH

sandramycin

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