(1S,2R,5S,6R)-5-(3'-(benzyloxy)propyl)-1,2-dimethyl-3,9-dioxabicyclo<4.2.1>nonan-4-one

Base Information

• Chemical Name: (1S,2R,5S,6R)-5-(3'-(benzyloxy)propyl)-1,2-dimethyl-3,9-dioxabicyclo<4.2.1>nonan-4-one
• CAS No.: 128440-50-6
• Molecular Formula: C₁₉H₂₆O₄
• Molecular Weight: 318.413
• Mol file: 128440-50-6.mol

Synonyms:(1S,2R,5S,6R)-5-(3'-(benzyloxy)propyl)-1,2-dimethyl-3,9-dioxabicyclo<4.2.1>nonan-4-one

Chemical Property of (1S,2R,5S,6R)-5-(3'-(benzyloxy)propyl)-1,2-dimethyl-3,9-dioxabicyclo<4.2.1>nonan-4-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2R,5S,6R)-5-(3'-(benzyloxy)propyl)-1,2-dimethyl-3,9-dioxabicyclo<4.2.1>nonan-4-one

There total 1 articles about (1S,2R,5S,6R)-5-(3'-(benzyloxy)propyl)-1,2-dimethyl-3,9-dioxabicyclo<4.2.1>nonan-4-one 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:

(+)-(4S)-3-<5-(benzyloxy)-(2S)-<(2R,5S)-5-methyl-5-<(1R)-1-hydroxyethyl>tetrahydrofuranyl>pentanoyl>-4-isopropyl-1,3-oxazolidin-2-one (128329-75-9) → (1S,2R,5S,6R)-5-(3'-(benzyloxy)propyl)-1,2-dimethyl-3,9-dioxabicyclo<4.2.1>nonan-4-one (128440-50-6)

Guidance literature:

With phenylmagnesium bromide; lithium bromide; Yield given. Multistep reaction; 1.) THF, -78 deg C, 2 h, 2.) 20 deg C, 24 h;

DOI:10.1021/ja00169a042

Reference yield: 94.0%

(1S,2R,5S,6R)-5-(3'-(benzyloxy)propyl)-1,2-dimethyl-3,9-dioxabicyclo<4.2.1>nonan-4-one (128440-50-6) → (1S,2R,5S,6R)-5-(3'-(benzyloxy)propyl)-1,2-dimethyl-4-methylene-3,9-dioxabicyclo<4.2.1>nonane (128329-76-0)

Guidance literature:

With pyridine; In tetrahydrofuran; toluene; 1.) -45 deg C, 40 min, 2.) 20 deg C, 45 min;

DOI:10.1021/ja00169a042

Reference yield:

(1S,2R,5S,6R)-5-(3'-(benzyloxy)propyl)-1,2-dimethyl-3,9-dioxabicyclo<4.2.1>nonan-4-one (128440-50-6) → (Z)-(S)-6-[(4S,5S,6R)-6-((R)-2-Benzyloxy-1-methyl-ethyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-2-[(2R,5S)-5-((R)-1-hydroxy-ethyl)-5-methyl-tetrahydro-furan-2-yl]-hex-5-en-2-ol (128329-84-0)

Guidance literature:

Multi-step reaction with 11 steps

1: 94 percent / pyridine / tetrahydrofuran; toluene / 1.) -45 deg C, 40 min, 2.) 20 deg C, 45 min

2: 100 percent / pyridinium tosylate / CH₂Cl₂ / 6 h / 20 °C

3: 1.) ozone, 2.) dimethyl sulfide / 1.) CH₂Cl₂, -78 deg C, 2a.) -78 deg C, 1 h, 2b.) 20 deg C, 1 h

4: 55 percent / CH₂Cl₂; diethyl ether / 1.) -78 deg C, 8 h, 2.) 20 deg C, 2 h

5: 94 percent / triethylamine / CH₂Cl₂ / 2 h / 0 °C

6: 100 percent / H₂ / 10percent Pd/C / ethyl acetate / 19 h / 20 °C / 3040 Torr

7: 1.88 g / triethylamine / CH₂Cl₂ / 3 h / 0 °C

8: 1.84 g / NaI, NaHCO₃, diisopropylethylamine / acetone / 18 h / 20 °C

9: 78 percent / diisopropylethylamine / toluene; acetonitrile / 54 h / 75 °C

10: 1.) sodium bis(trimethylsilyl)amide / 1.) toluene, 20 deg C, 15 min, 2a.) -78 deg C, 15 min, 2b.) 20 deg C, 30 min

11: 94 percent / Bu₄NF / tetrahydrofuran / 36 h / 80 °C

With pyridine; dimethylsulfide; tetrabutyl ammonium fluoride; hydrogen; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; ozone; triethylamine; N-ethyl-N,N-diisopropylamine; sodium iodide; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; dichloromethane; ethyl acetate; acetone; toluene; acetonitrile;

DOI:10.1021/ja00169a042

upstream raw materials:

(+)-(4S)-3-<5-(benzyloxy)-(2S)-<(2R,5S)-5-methyl-5-<(1R)-1-hydroxyethyl>tetrahydrofuranyl>pentanoyl>-4-isopropyl-1,3-oxazolidin-2-one

Downstream raw materials:

(1S,2R,5S,6R)-5-(3'-(benzyloxy)propyl)-1,2-dimethyl-4-methylene-3,9-dioxabicyclo<4.2.1>nonane

(1S,2R,6R,4Z)-5-(3'-(benzyloxy)propyl)-1,2,4-trimethyl-3,9-dioxabicyclo<4.2.1>non-4-ene

(1'R,2R,5S)-5-(1'-acetoxyethyl)-5-methyl-2-(1''-oxo-4''-(benzyloxy)butyl)tetrahydrofuran

(Z)-(S)-6-[(4S,5S,6R)-6-((R)-2-Benzyloxy-1-methyl-ethyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-2-[(2R,5S)-5-((R)-1-hydroxy-ethyl)-5-methyl-tetrahydro-furan-2-yl]-hex-5-en-2-ol