(S)-triisopropyl[1-(triphenylmethoxy)pent-4-en-2-yloxy]silane

Base Information

• Chemical Name: (S)-triisopropyl[1-(triphenylmethoxy)pent-4-en-2-yloxy]silane
• CAS No.: 1515605-70-5
• Molecular Formula: C₃₃H₄₄O₂Si
• Molecular Weight: 500.797
• Mol file: 1515605-70-5.mol

Synonyms:(S)-triisopropyl[1-(triphenylmethoxy)pent-4-en-2-yloxy]silane

Chemical Property of (S)-triisopropyl[1-(triphenylmethoxy)pent-4-en-2-yloxy]silane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-triisopropyl[1-(triphenylmethoxy)pent-4-en-2-yloxy]silane

There total 1 articles about (S)-triisopropyl[1-(triphenylmethoxy)pent-4-en-2-yloxy]silane 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: 91.0%

triisopropylsilyl trifluoromethanesulfonate (80522-42-5) + (2S)-1-triphenylmethoxy-4-pentene-2-ol (170277-82-4) → (S)-triisopropyl[1-(triphenylmethoxy)pent-4-en-2-yloxy]silane (1515605-70-5)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; at 0 - 20 ℃; for 2h; Inert atmosphere;

DOI:10.1021/ol403319m

Reference yield: 79.0%

(S)-triisopropyl[1-(triphenylmethoxy)pent-4-en-2-yloxy]silane (1515605-70-5) → 4(S)-triisopropylsilyloxy-5-triphenylmethoxy-1-pentanol (1515605-73-8)

Guidance literature:

(S)-triisopropyl[1-(triphenylmethoxy)pent-4-en-2-yloxy]silane; With borane-THF; In tetrahydrofuran; at 0 - 20 ℃; for 4h; Inert atmosphere;

With dihydrogen peroxide; sodium hydroxide; In tetrahydrofuran; water; at 0 - 20 ℃; for 12h;

DOI:10.1021/ol403319m

Reference yield:

(S)-triisopropyl[1-(triphenylmethoxy)pent-4-en-2-yloxy]silane (1515605-70-5) → C61H88N10O19 (1574776-16-1)

Guidance literature:

Multi-step reaction with 12 steps

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

1.2: 12 h / 0 - 20 °C

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

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

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

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

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

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

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

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

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

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

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

With morpholine; dmap; tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium azide; borane-THF; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; sulfur trioxide pyridine complex; trimethylamine hydrochloride; tetra-(n-butyl)ammonium iodide; sodium hydrogencarbonate; dimethyl sulfoxide; triethylamine; 3-[(diethoxyphosphinyl)oxy]-1,2,3-benzotriazin-4(3H)-one; zinc dibromide; triethylphosphine; In tetrahydrofuran; methanol; dichloromethane; 2,2,2-trifluoroethanol; N,N-dimethyl-formamide; toluene; acetonitrile; 7.1: |Ugi Condensation;

DOI:10.1021/ol403319m

upstream raw materials:

triisopropylsilyl trifluoromethanesulfonate

(2S)-1-triphenylmethoxy-4-pentene-2-ol

Downstream raw materials:

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

C₄₅H₇₃N₅O₁₂Si

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