(S)-2-((2S,4R,5R)-4-acetoxy-5-((R)-5-((2R,6R)-6-((E)-5-((tertbutyldiphenylsilyl)oxy)pent-1-en-1-yl)-2-methoxy-3,6-dihydro-2H-pyran-2-yl)-2-methyl-3-oxopent-4-yn-1-yl)tetrahydrofuran-2-yl)-2-((triisopropylsilyl)oxy)ethylpivalate

Base Information

Chemical Name:(S)-2-((2S,4R,5R)-4-acetoxy-5-((R)-5-((2R,6R)-6-((E)-5-((tertbutyldiphenylsilyl)oxy)pent-1-en-1-yl)-2-methoxy-3,6-dihydro-2H-pyran-2-yl)-2-methyl-3-oxopent-4-yn-1-yl)tetrahydrofuran-2-yl)-2-((triisopropylsilyl)oxy)ethylpivalate
CAS No.:1431879-97-8
Molecular Formula:C₅₅H₈₂O₁₀Si₂
Molecular Weight:959.421
Hs Code.:

(S)-2-((2S,4R,5R)-4-acetoxy-5-((R)-5-((2R,6R)-6-((E)-5-((tertbutyldiphenylsilyl)oxy)pent-1-en-1-yl)-2-methoxy-3,6-dihydro-2H-pyran-2-yl)-2-methyl-3-oxopent-4-yn-1-yl)tetrahydrofuran-2-yl)-2-((triisopropylsilyl)oxy)ethylpivalate

Synonyms:(S)-2-((2S,4R,5R)-4-acetoxy-5-((R)-5-((2R,6R)-6-((E)-5-((tertbutyldiphenylsilyl)oxy)pent-1-en-1-yl)-2-methoxy-3,6-dihydro-2H-pyran-2-yl)-2-methyl-3-oxopent-4-yn-1-yl)tetrahydrofuran-2-yl)-2-((triisopropylsilyl)oxy)ethylpivalate

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Chemical Property of (S)-2-((2S,4R,5R)-4-acetoxy-5-((R)-5-((2R,6R)-6-((E)-5-((tertbutyldiphenylsilyl)oxy)pent-1-en-1-yl)-2-methoxy-3,6-dihydro-2H-pyran-2-yl)-2-methyl-3-oxopent-4-yn-1-yl)tetrahydrofuran-2-yl)-2-((triisopropylsilyl)oxy)ethylpivalate

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Technology Process of (S)-2-((2S,4R,5R)-4-acetoxy-5-((R)-5-((2R,6R)-6-((E)-5-((tertbutyldiphenylsilyl)oxy)pent-1-en-1-yl)-2-methoxy-3,6-dihydro-2H-pyran-2-yl)-2-methyl-3-oxopent-4-yn-1-yl)tetrahydrofuran-2-yl)-2-((triisopropylsilyl)oxy)ethylpivalate

There total 29 articles about (S)-2-((2S,4R,5R)-4-acetoxy-5-((R)-5-((2R,6R)-6-((E)-5-((tertbutyldiphenylsilyl)oxy)pent-1-en-1-yl)-2-methoxy-3,6-dihydro-2H-pyran-2-yl)-2-methyl-3-oxopent-4-yn-1-yl)tetrahydrofuran-2-yl)-2-((triisopropylsilyl)oxy)ethylpivalate 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: 77.0%

: 1431879-83-2
C₅₅H₈₄O₁₀Si₂

: 1431879-97-8
(S)-2-((2S,4R,5R)-4-acetoxy-5-((R)-5-((2R,6R)-6-((E)-5-((tertbutyldiphenylsilyl)oxy)pent-1-en-1-yl)-2-methoxy-3,6-dihydro-2H-pyran-2-yl)-2-methyl-3-oxopent-4-yn-1-yl)tetrahydrofuran-2-yl)-2-((triisopropylsilyl)oxy)ethylpivalate

Guidance literature:: With sulfur trioxide pyridine complex; N-ethyl-N,N-diisopropylamine; In dichloromethane; dimethyl sulfoxide; at 20 ℃; for 0.0833333h;
DOI:10.1021/ol400487e

Reference yield:

: 1431879-67-2
tert-butyl(((E)-5-((2R,6R)-6-(iodoethynyl)-6-methoxy-5,6-dihydro-2H-pyran-2-yl)pent-4-en-1-yl)oxy)diphenylsilane

: 1431879-97-8
(S)-2-((2S,4R,5R)-4-acetoxy-5-((R)-5-((2R,6R)-6-((E)-5-((tertbutyldiphenylsilyl)oxy)pent-1-en-1-yl)-2-methoxy-3,6-dihydro-2H-pyran-2-yl)-2-methyl-3-oxopent-4-yn-1-yl)tetrahydrofuran-2-yl)-2-((triisopropylsilyl)oxy)ethylpivalate

Guidance literature:: Multi-step reaction with 2 steps

1: chromium dichloride; nickel dichloride / tetrahydrofuran / 12 h / 20 °C / Inert atmosphere

2: N-ethyl-N,N-diisopropylamine; sulfur trioxide pyridine complex / dichloromethane; dimethyl sulfoxide / 0.08 h / 20 °C

With chromium dichloride; sulfur trioxide pyridine complex; N-ethyl-N,N-diisopropylamine; nickel dichloride; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide;
DOI:10.1021/ol400487e

Reference yield:

: 1431879-91-2
(2R,3S)-ethyl 3-hydroxy-2-((triisopropylsilyl)oxy)butanoate

: 1431879-97-8
(S)-2-((2S,4R,5R)-4-acetoxy-5-((R)-5-((2R,6R)-6-((E)-5-((tertbutyldiphenylsilyl)oxy)pent-1-en-1-yl)-2-methoxy-3,6-dihydro-2H-pyran-2-yl)-2-methyl-3-oxopent-4-yn-1-yl)tetrahydrofuran-2-yl)-2-((triisopropylsilyl)oxy)ethylpivalate

Guidance literature:: Multi-step reaction with 11 steps

1.1: diisobutylaluminium hydride / dichloromethane; toluene / 0.5 h / 0 - 20 °C / Inert atmosphere

2.1: dmap; pyridine / dichloromethane / 12 h / 20 °C / Inert atmosphere

3.1: N-ethyl-N,N-diisopropylamine; sulfur trioxide pyridine complex / dichloromethane; dimethyl sulfoxide / 0.33 h / 0 °C / Inert atmosphere

4.1: triethylamine / dichloromethane / 0.5 h / 20 °C / Inert atmosphere

5.1: tin(IV) chloride / dichloromethane / 0.17 h / -78 °C / Inert atmosphere

5.2: 0.42 h / -78 °C / Inert atmosphere

6.1: dmap; pyridine / dichloromethane / 0.08 h / 20 °C / Inert atmosphere

7.1: Pd(OH)2/C; hydrogen / ethyl acetate / 0.25 h / 20 °C

8.1: tin(IV) chloride; triethylsilane / dichloromethane / 1 h / -78 - -30 °C / Inert atmosphere

9.1: N-ethyl-N,N-diisopropylamine; sulfur trioxide pyridine complex / dichloromethane; dimethyl sulfoxide / 0.08 h / 0 °C / Inert atmosphere

10.1: chromium dichloride; nickel dichloride / tetrahydrofuran / 12 h / 20 °C / Inert atmosphere

11.1: N-ethyl-N,N-diisopropylamine; sulfur trioxide pyridine complex / dichloromethane; dimethyl sulfoxide / 0.08 h / 20 °C

With pyridine; chromium dichloride; triethylsilane; dmap; Pd(OH)2/C; hydrogen; sulfur trioxide pyridine complex; tin(IV) chloride; diisobutylaluminium hydride; triethylamine; N-ethyl-N,N-diisopropylamine; nickel dichloride; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; ethyl acetate; toluene; 4.1: |Sharpless Dihydroxylation / 5.1: |Mukaiyama Aldol Addition / 9.1: |Parikh-Doering Oxidation;
DOI:10.1021/ol400487e