(1R,3S)-3-[(2S,5S,6S)-6-((1S)-2-hydroxy-1-methylethyl)-5-methyltetrahydro-2H-pyran-2-yl]-1-methyl-2-oxobutyl benzoate

Base Information

• Chemical Name: (1R,3S)-3-[(2S,5S,6S)-6-((1S)-2-hydroxy-1-methylethyl)-5-methyltetrahydro-2H-pyran-2-yl]-1-methyl-2-oxobutyl benzoate
• CAS No.: 460997-50-6
• Molecular Formula: C₂₁H₃₀O₅
• Molecular Weight: 362.466
• Mol file: 460997-50-6.mol

Synonyms:(1R,3S)-3-[(2S,5S,6S)-6-((1S)-2-hydroxy-1-methylethyl)-5-methyltetrahydro-2H-pyran-2-yl]-1-methyl-2-oxobutyl benzoate

Chemical Property of (1R,3S)-3-[(2S,5S,6S)-6-((1S)-2-hydroxy-1-methylethyl)-5-methyltetrahydro-2H-pyran-2-yl]-1-methyl-2-oxobutyl benzoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,3S)-3-[(2S,5S,6S)-6-((1S)-2-hydroxy-1-methylethyl)-5-methyltetrahydro-2H-pyran-2-yl]-1-methyl-2-oxobutyl benzoate

There total 6 articles about (1R,3S)-3-[(2S,5S,6S)-6-((1S)-2-hydroxy-1-methylethyl)-5-methyltetrahydro-2H-pyran-2-yl]-1-methyl-2-oxobutyl benzoate 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:

C21H29BrHgO5 → (1R,3S)-3-[(2S,5S,6S)-6-((1S)-2-hydroxy-1-methylethyl)-5-methyltetrahydro-2H-pyran-2-yl]-1-methyl-2-oxobutyl benzoate (460997-50-6)

Guidance literature:

With tri-n-butyl-tin hydride; In tetrahydrofuran; toluene; at 20 - 60 ℃;

DOI:10.1002/1521-3773(20020617)41:12<2144::AID-ANIE2144>3.0.CO;2-E

Reference yield:

ethyl (E),(4R)-4-((1R,2R)-2-{[(tert-butyldiphenylsilyl)oxy]methyl}cyclopropyl)pent-2-enoate (460997-44-8) → (1R,3S)-3-[(2S,5S,6S)-6-((1S)-2-hydroxy-1-methylethyl)-5-methyltetrahydro-2H-pyran-2-yl]-1-methyl-2-oxobutyl benzoate (460997-50-6)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 97 percent / H₂ / PtO₂ / ethyl acetate / 6 h

2.1: 97 percent / Dibal-H / toluene; hexane / 1 h / -78 °C

3.1: (c-Hex)2BCl; EtNMe₂ / diethyl ether / 2 h / 0 °C

3.2: diethyl ether / 20 h / -78 - -23 °C

3.3: 83 percent / phosphate buffer; aq. H₂O₂ / diethyl ether; methanol / 1 h / 0 °C

4.1: 86 percent / HF*pyridine / tetrahydrofuran / 2 h / 20 °C

5.1: Hg(OCOCF₃)2 / CH₂Cl₂ / 0.5 h / 20 °C

5.2: KBr / CH₂Cl₂; H₂O / 0.33 h

5.3: AIBN; n-Bu₃SnH / tetrahydrofuran; toluene / 2 h / 20 - 55 °C

With N,N-dimethyl-ethanamine; dicyclohexylboron chloride; hydrogen; mercury(II) trifluoroacetate; diisobutylaluminium hydride; pyridine hydrogenfluoride; platinum(IV) oxide; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; ethyl acetate; toluene;

DOI:10.1021/jo0496042

Reference yield:

(1S,3S,4S,7S)-4-hydroxy-7-[(1R,2R)-2-(hydroxymethyl)cyclopropyl]-1,3-dimethyl-2-oxooctyl benzoate (460997-49-3) → (1R,3S)-3-[(2S,5S,6S)-6-((1S)-2-hydroxy-1-methylethyl)-5-methyltetrahydro-2H-pyran-2-yl]-1-methyl-2-oxobutyl benzoate (460997-50-6) + (1R,3S)-3-[(2S,5S,6R)-6-((1S)-2-hydroxy-1-methylethyl)-5-methyltetrahydro-2H-pyran-2-yl]-1-methyl-2-oxobutyl benzoate

Guidance literature:

(1S,3S,4S,7S)-4-hydroxy-7-[(1R,2R)-2-(hydroxymethyl)cyclopropyl]-1,3-dimethyl-2-oxooctyl benzoate; With mercury(II) trifluoroacetate; In dichloromethane; at 20 ℃; for 0.5h;

With potassium bromide; In dichloromethane; water; for 0.333333h;

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In tetrahydrofuran; toluene; at 20 - 55 ℃; for 2h; Title compound not separated from byproducts;

DOI:10.1021/jo0496042

upstream raw materials:

(1S,3S,4S,7S)-4-hydroxy-7-[(1R,2R)-2-(hydroxymethyl)cyclopropyl]-1,3-dimethyl-2-oxooctyl benzoate

(4S)-4-((1R,2R)-2-{[(tert-butyldiphenylsilyl)oxy]methyl}cyclopropyl)pentanal

ethyl (E),(4R)-4-((1R,2R)-2-{[(tert-butyldiphenylsilyl)oxy]methyl}cyclopropyl)pent-2-enoate

ethyl (4S)-4-((1R,2R)-2-{[(tert-butyldiphenylsilyl)oxy]methyl}cyclopropyl)pentanoate

Downstream raw materials:

methyl (2S)-2-((2S,5S,6S)-6-[(1S)-2-[(tert-butyldiphenylsilyl)oxy]-1-methylethyl]-5-methyltetrahydro-2H-pyran-2-yl)propanoate

(2S)-2-((2S,5S,6S)-6-[(1S)-2-[(tert-butyldiphenylsilyl)oxy]-1-methylethyl]-5-methyltetrahydro-2H-pyran-2-yl)propanoic acid

(S)-2-{(2S,5S,6S)-6-[(S)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-5-methyl-tetrahydro-pyran-2-yl}-propionaldehyde

(1R,3S)-3-[(2S,5S,6S)-6-{(1S)-2-[(tert-butyldiphenylsilyl)oxy]-1-methylethyl}-5-methyltetrahydro-2H-pyran-2-yl]-1-methyl-2-oxobutyl benzoate