(R)-6-[(2S,4S)-2,4-Bis-(4-methoxy-benzyloxy)-8-phenyl-octyl]-5,6-dihydro-pyran-2-one

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Chemical Name:(R)-6-[(2S,4S)-2,4-Bis-(4-methoxy-benzyloxy)-8-phenyl-octyl]-5,6-dihydro-pyran-2-one
CAS No.:868566-30-7
Molecular Formula:C₃₅H₄₂O₆
Molecular Weight:558.715
Hs Code.:

Synonyms:(R)-6-[(2S,4S)-2,4-Bis-(4-methoxy-benzyloxy)-8-phenyl-octyl]-5,6-dihydro-pyran-2-one

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Chemical Property of (R)-6-[(2S,4S)-2,4-Bis-(4-methoxy-benzyloxy)-8-phenyl-octyl]-5,6-dihydro-pyran-2-one

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Technology Process of (R)-6-[(2S,4S)-2,4-Bis-(4-methoxy-benzyloxy)-8-phenyl-octyl]-5,6-dihydro-pyran-2-one

There total 17 articles about (R)-6-[(2S,4S)-2,4-Bis-(4-methoxy-benzyloxy)-8-phenyl-octyl]-5,6-dihydro-pyran-2-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: 95.0%

: 868566-37-4
(Z)-(5R,7R,9S)-5-Hydroxy-7,9-bis-(4-methoxy-benzyloxy)-13-phenyl-tridec-2-enoic acid methyl ester

: 868566-30-7
(R)-6-[(2S,4S)-2,4-Bis-(4-methoxy-benzyloxy)-8-phenyl-octyl]-5,6-dihydro-pyran-2-one

Guidance literature:: With pyridinium p-toluenesulfonate; In chloroform; for 6h; Heating;
DOI:10.1021/jo050972v

Reference yield:

: 868566-22-7
2-O-benzyl-3,5-dideoxy-6,7-O-isopropylidene-D-xyloheptoic-γ-lactone

: 868566-30-7
(R)-6-[(2S,4S)-2,4-Bis-(4-methoxy-benzyloxy)-8-phenyl-octyl]-5,6-dihydro-pyran-2-one

Guidance literature:: Multi-step reaction with 12 steps

1.1: 97 percent / DIBAL-H / CH₂Cl₂; toluene / 0.5 h / -78 °C

2.1: n-BuLi / tetrahydrofuran; hexane / 1 h / 20 °C

2.2: 96 percent / tetrahydrofuran; hexane / 12 h / 20 °C

3.1: 69 percent / diethyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 2 h / 0 °C

4.1: 96 percent / H₂ / Raney nickel / ethanol / 12 h / 1034.3 Torr

5.1: 95 percent / Na / methanol / 2 h / 20 °C

6.1: 91 percent / NaH / dimethylformamide / 6 h / 20 °C

7.1: 94 percent / pyridinium p-toluenesulfonate / methanol / 24 h / 20 °C

8.1: triethylamine; 4-dimethylaminopyridine / CH₂Cl₂ / 1 h / 20 °C

9.1: 375 mg / K₂CO₃ / methanol / 0.5 h

10.1: n-BuLi / tetrahydrofuran; hexane / 0.25 h / -78 °C

10.2: BF₃*Et₂O / tetrahydrofuran; hexane / 0.25 h / -78 °C

10.3: 93 percent / tetrahydrofuran; hexane / 0.5 h / -78 °C

11.1: 72 percent / H₂; quinoline / Pd/CaCO₃ / benzene

12.1: 95 percent / pyridinium p-toluenesulfonate / CHCl₃ / 6 h / Heating

With quinoline; dmap; n-butyllithium; hydrogen; sodium; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; potassium carbonate; triethylamine; triphenylphosphine; diethylazodicarboxylate; Lindlar's catalyst; nickel; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; chloroform; N,N-dimethyl-formamide; toluene; benzene; 2.2: Wittig olefination reaction / 3.1: Mitsunobu reaction;
DOI:10.1021/jo050972v

Reference yield:

: (3R,5S)-3-Benzyloxy-5-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-tetrahydro-furan-2-ol

: 868566-30-7
(R)-6-[(2S,4S)-2,4-Bis-(4-methoxy-benzyloxy)-8-phenyl-octyl]-5,6-dihydro-pyran-2-one

Guidance literature:: Multi-step reaction with 11 steps

1.1: n-BuLi / tetrahydrofuran; hexane / 1 h / 20 °C

1.2: 96 percent / tetrahydrofuran; hexane / 12 h / 20 °C

2.1: 69 percent / diethyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 2 h / 0 °C

3.1: 96 percent / H₂ / Raney nickel / ethanol / 12 h / 1034.3 Torr

4.1: 95 percent / Na / methanol / 2 h / 20 °C

5.1: 91 percent / NaH / dimethylformamide / 6 h / 20 °C

6.1: 94 percent / pyridinium p-toluenesulfonate / methanol / 24 h / 20 °C

7.1: triethylamine; 4-dimethylaminopyridine / CH₂Cl₂ / 1 h / 20 °C

8.1: 375 mg / K₂CO₃ / methanol / 0.5 h

9.1: n-BuLi / tetrahydrofuran; hexane / 0.25 h / -78 °C

9.2: BF₃*Et₂O / tetrahydrofuran; hexane / 0.25 h / -78 °C

9.3: 93 percent / tetrahydrofuran; hexane / 0.5 h / -78 °C

10.1: 72 percent / H₂; quinoline / Pd/CaCO₃ / benzene

11.1: 95 percent / pyridinium p-toluenesulfonate / CHCl₃ / 6 h / Heating

With quinoline; dmap; n-butyllithium; hydrogen; sodium; pyridinium p-toluenesulfonate; sodium hydride; potassium carbonate; triethylamine; triphenylphosphine; diethylazodicarboxylate; Lindlar's catalyst; nickel; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; chloroform; N,N-dimethyl-formamide; benzene; 1.2: Wittig olefination reaction / 2.1: Mitsunobu reaction;
DOI:10.1021/jo050972v