(2S,5R,6R,8R)-6-(benzyloxy)-9-((tert-butyldimethylsilyl)oxy)-5-hydroxy-8-methyl-3-oxo-2-((triisopropylsilyl)oxy)nonyl pivalate

Base Information

• Chemical Name: (2S,5R,6R,8R)-6-(benzyloxy)-9-((tert-butyldimethylsilyl)oxy)-5-hydroxy-8-methyl-3-oxo-2-((triisopropylsilyl)oxy)nonyl pivalate
• CAS No.: 1431879-81-0
• Molecular Formula: C₃₇H₆₈O₇Si₂
• Molecular Weight: 681.114

Synonyms:(2S,5R,6R,8R)-6-(benzyloxy)-9-((tert-butyldimethylsilyl)oxy)-5-hydroxy-8-methyl-3-oxo-2-((triisopropylsilyl)oxy)nonyl pivalate

Chemical Property of (2S,5R,6R,8R)-6-(benzyloxy)-9-((tert-butyldimethylsilyl)oxy)-5-hydroxy-8-methyl-3-oxo-2-((triisopropylsilyl)oxy)nonyl pivalate

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of (2S,5R,6R,8R)-6-(benzyloxy)-9-((tert-butyldimethylsilyl)oxy)-5-hydroxy-8-methyl-3-oxo-2-((triisopropylsilyl)oxy)nonyl pivalate

There total 9 articles about (2S,5R,6R,8R)-6-(benzyloxy)-9-((tert-butyldimethylsilyl)oxy)-5-hydroxy-8-methyl-3-oxo-2-((triisopropylsilyl)oxy)nonyl pivalate 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: 76.0%

(2R,4R)-2-(benzyloxy)-5-((tert-butyldimethylsilyl)oxy)-4-methylpentanal (1431879-78-5) + (S)-2-((triisopropylsilyl)oxy)-3-((trimethylsilyl)oxy)but-3-en-1-yl pivalate (1431879-80-9) → (2S,5R,6R,8R)-6-(benzyloxy)-9-((tert-butyldimethylsilyl)oxy)-5-hydroxy-8-methyl-3-oxo-2-((triisopropylsilyl)oxy)nonyl pivalate (1431879-81-0) + (2S,6R,8R)-6-(benzyloxy)-9-((tert-butyldimethylsilyl)oxy)-5-hydroxy-8-methyl-3-oxo-2-((triisopropylsilyl)oxy)nonyl pivalate

Guidance literature:

(2R,4R)-2-(benzyloxy)-5-((tert-butyldimethylsilyl)oxy)-4-methylpentanal; With tin(IV) chloride; In dichloromethane; at -78 ℃; for 0.166667h; Inert atmosphere;

(S)-2-((triisopropylsilyl)oxy)-3-((trimethylsilyl)oxy)but-3-en-1-yl pivalate; In dichloromethane; at -78 ℃; for 0.416667h; Inert atmosphere;

DOI:10.1021/ol400487e

Reference yield:

(2R,4R)-2-(benzyloxy)-5-((tert-butyldimethylsilyl)oxy)-4-methylpentan-1-ol (1431879-89-8) → (2S,5R,6R,8R)-6-(benzyloxy)-9-((tert-butyldimethylsilyl)oxy)-5-hydroxy-8-methyl-3-oxo-2-((triisopropylsilyl)oxy)nonyl pivalate (1431879-81-0) + (2S,6R,8R)-6-(benzyloxy)-9-((tert-butyldimethylsilyl)oxy)-5-hydroxy-8-methyl-3-oxo-2-((triisopropylsilyl)oxy)nonyl pivalate

Guidance literature:

Multi-step reaction with 2 steps

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

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

2.2: 0.42 h / -78 °C / Inert atmosphere

With sulfur trioxide pyridine complex; tin(IV) chloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; dimethyl sulfoxide; 2.1: |Mukaiyama Aldol Addition;

DOI:10.1021/ol400487e

Reference yield:

(2R,3S)-ethyl 3-hydroxy-2-((triisopropylsilyl)oxy)butanoate (1431879-91-2) → (2S,5R,6R,8R)-6-(benzyloxy)-9-((tert-butyldimethylsilyl)oxy)-5-hydroxy-8-methyl-3-oxo-2-((triisopropylsilyl)oxy)nonyl pivalate (1431879-81-0) + (2S,6R,8R)-6-(benzyloxy)-9-((tert-butyldimethylsilyl)oxy)-5-hydroxy-8-methyl-3-oxo-2-((triisopropylsilyl)oxy)nonyl pivalate

Guidance literature:

Multi-step reaction with 5 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

With pyridine; dmap; sulfur trioxide pyridine complex; tin(IV) chloride; diisobutylaluminium hydride; triethylamine; N-ethyl-N,N-diisopropylamine; In dichloromethane; dimethyl sulfoxide; toluene; 4.1: |Sharpless Dihydroxylation / 5.1: |Mukaiyama Aldol Addition;

DOI:10.1021/ol400487e

upstream raw materials:

(2R,4R)-2-(benzyloxy)-5-((tert-butyldimethylsilyl)oxy)-4-methylpentan-1-ol

(2R,4R)-2-(benzyloxy)-5-((tert-butyldimethylsilyl)oxy)-4-methylpentanal

(S)-2-((triisopropylsilyl)oxy)-3-((trimethylsilyl)oxy)but-3-en-1-yl pivalate

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

Downstream raw materials:

(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

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

(2S)-2-[(2R,3R,4aR,5'R,6S,6''R,7aR)-6''[(1E)-5-[(tert-butyldiphenylsilyl)oxy]pent-1-en-1-yl]-3-methyl-3,3''4,4a,6,6'',7,7a-octahydrodispiro[furo[3,2-b]pyran-2,2'-oxolane-5',2''-pyran]-6-yl]-2-((triisopropylsilyl)oxy)ethyl pivalate

C₅₅H₈₄O₁₀Si₂

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