(2S,6S)-2-((2S,4S,6S)-6-(benzyloxy)-4-methoxy-2-methylnonyl)-6-(2-(benzyloxy)ethyl)dihydro-2H-pyran-4(3H)-one

Base Information

• Chemical Name: (2S,6S)-2-((2S,4S,6S)-6-(benzyloxy)-4-methoxy-2-methylnonyl)-6-(2-(benzyloxy)ethyl)dihydro-2H-pyran-4(3H)-one
• CAS No.: 1403354-29-9
• Molecular Formula: C₃₂H₄₆O₅
• Molecular Weight: 510.714
• Mol file: 1403354-29-9.mol

Synonyms:(2S,6S)-2-((2S,4S,6S)-6-(benzyloxy)-4-methoxy-2-methylnonyl)-6-(2-(benzyloxy)ethyl)dihydro-2H-pyran-4(3H)-one

Chemical Property of (2S,6S)-2-((2S,4S,6S)-6-(benzyloxy)-4-methoxy-2-methylnonyl)-6-(2-(benzyloxy)ethyl)dihydro-2H-pyran-4(3H)-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,6S)-2-((2S,4S,6S)-6-(benzyloxy)-4-methoxy-2-methylnonyl)-6-(2-(benzyloxy)ethyl)dihydro-2H-pyran-4(3H)-one

There total 20 articles about (2S,6S)-2-((2S,4S,6S)-6-(benzyloxy)-4-methoxy-2-methylnonyl)-6-(2-(benzyloxy)ethyl)dihydro-2H-pyran-4(3H)-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: 48.0%

(3S,9R,11S,13S,E)-1,13-bis(benzyloxy)-3-hydroxy-11-methoxy-9-methylhexadec-6-en-5-one (1403354-18-6) → (2R,6S)-2-((2S,4S,6S)-6-(benzyloxy)-4-methoxy-2-methylnonyl)-6-(2-(benzyloxy)ethyl)dihydro-2H-pyran-4(3H)-one (1403354-26-6) + (2S,6S)-2-((2S,4S,6S)-6-(benzyloxy)-4-methoxy-2-methylnonyl)-6-(2-(benzyloxy)ethyl)dihydro-2H-pyran-4(3H)-one (1403354-29-9)

Guidance literature:

With tetrakis(acetonitrile)palladium(II) bis(tetrafluoroborate); In dichloromethane; at 20 ℃; for 12h; Inert atmosphere;

DOI:10.1021/jo301425c

Reference yield:

(S)-(-)-2-methyl-4-penten-1-ol (5673-98-3,63501-27-9,88080-30-2,63501-26-8) → (2R,6S)-2-((2S,4S,6S)-6-(benzyloxy)-4-methoxy-2-methylnonyl)-6-(2-(benzyloxy)ethyl)dihydro-2H-pyran-4(3H)-one (1403354-26-6) + (2S,6S)-2-((2S,4S,6S)-6-(benzyloxy)-4-methoxy-2-methylnonyl)-6-(2-(benzyloxy)ethyl)dihydro-2H-pyran-4(3H)-one (1403354-29-9)

Guidance literature:

Multi-step reaction with 15 steps

1.1: triethylamine; dmap / dichloromethane / 12 h / 0 - 20 °C

2.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 10 h / 0 - 20 °C

3.1: (S,S)-[N,N-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexane-diamino]cobalt(III) acetate; acetic acid; water / toluene / 24 h / 20 °C / Cooling with ice

4.1: copper(l) iodide / tetrahydrofuran / 0.08 h / -20 °C / Inert atmosphere

4.2: 1 h / -40 - -20 °C / Inert atmosphere

5.1: potassium hydride / tetrahydrofuran / 0.5 h / 0 - 20 °C

6.1: (R,R)-Jacobsen catalyst; acetic acid; water / toluene / 24 h / 20 °C / Cooling with ice

7.1: copper(l) iodide / tetrahydrofuran / 1 h / -40 - 20 °C

8.1: trifluorormethanesulfonic acid / dichloromethane; cyclohexane / 2 h / 0 - 20 °C

9.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 3 h / 0 - 20 °C

10.1: triethylamine; dmap / dichloromethane / 3 h / 0 - 20 °C

11.1: sodium iodide / dimethyl sulfoxide / 1 h / 90 °C

12.1: diisobutylaluminium hydride / dichloromethane / 1 h / -78 - 0 °C

12.2: 1 h / 0 °C

13.1: lithium chloride; N-ethyl-N,N-diisopropylamine / acetonitrile / 0.5 h / 20 °C

13.2: 12 h / Inert atmosphere

14.1: pyridine hydrogenfluoride / acetonitrile / 18 h / 0 - 20 °C

15.1: tetrakis(acetonitrile)palladium(II) bis(tetrafluoroborate) / dichloromethane / 12 h / 20 °C / Inert atmosphere

With dmap; tetrakis(acetonitrile)palladium(II) bis(tetrafluoroborate); copper(l) iodide; (S,S)-[N,N-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexane-diamino]cobalt(III) acetate; (R,R)-Jacobsen catalyst; trifluorormethanesulfonic acid; tetrabutyl ammonium fluoride; water; potassium hydride; diisobutylaluminium hydride; pyridine hydrogenfluoride; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; sodium iodide; lithium chloride; In tetrahydrofuran; dichloromethane; cyclohexane; dimethyl sulfoxide; toluene; acetonitrile; 13.1: |Horner-Wadsworth-Emmons Olefination / 13.2: |Horner-Wadsworth-Emmons Olefination / 15.1: |Michael Addition;

DOI:10.1021/jo301425c

Reference yield:

tert-butyl((S)-2-methyl-3-(oxiran-2-yl)propoxy)diphenylsilane → (2R,6S)-2-((2S,4S,6S)-6-(benzyloxy)-4-methoxy-2-methylnonyl)-6-(2-(benzyloxy)ethyl)dihydro-2H-pyran-4(3H)-one (1403354-26-6) + (2S,6S)-2-((2S,4S,6S)-6-(benzyloxy)-4-methoxy-2-methylnonyl)-6-(2-(benzyloxy)ethyl)dihydro-2H-pyran-4(3H)-one (1403354-29-9)

Guidance literature:

Multi-step reaction with 13 steps

1.1: (S,S)-[N,N-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexane-diamino]cobalt(III) acetate; acetic acid; water / toluene / 24 h / 20 °C / Cooling with ice

2.1: copper(l) iodide / tetrahydrofuran / 0.08 h / -20 °C / Inert atmosphere

2.2: 1 h / -40 - -20 °C / Inert atmosphere

3.1: potassium hydride / tetrahydrofuran / 0.5 h / 0 - 20 °C

4.1: (R,R)-Jacobsen catalyst; acetic acid; water / toluene / 24 h / 20 °C / Cooling with ice

5.1: copper(l) iodide / tetrahydrofuran / 1 h / -40 - 20 °C

6.1: trifluorormethanesulfonic acid / dichloromethane; cyclohexane / 2 h / 0 - 20 °C

7.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 3 h / 0 - 20 °C

8.1: triethylamine; dmap / dichloromethane / 3 h / 0 - 20 °C

9.1: sodium iodide / dimethyl sulfoxide / 1 h / 90 °C

10.1: diisobutylaluminium hydride / dichloromethane / 1 h / -78 - 0 °C

10.2: 1 h / 0 °C

11.1: lithium chloride; N-ethyl-N,N-diisopropylamine / acetonitrile / 0.5 h / 20 °C

11.2: 12 h / Inert atmosphere

12.1: pyridine hydrogenfluoride / acetonitrile / 18 h / 0 - 20 °C

13.1: tetrakis(acetonitrile)palladium(II) bis(tetrafluoroborate) / dichloromethane / 12 h / 20 °C / Inert atmosphere

With dmap; tetrakis(acetonitrile)palladium(II) bis(tetrafluoroborate); copper(l) iodide; (S,S)-[N,N-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexane-diamino]cobalt(III) acetate; (R,R)-Jacobsen catalyst; trifluorormethanesulfonic acid; tetrabutyl ammonium fluoride; water; potassium hydride; diisobutylaluminium hydride; pyridine hydrogenfluoride; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; sodium iodide; lithium chloride; In tetrahydrofuran; dichloromethane; cyclohexane; dimethyl sulfoxide; toluene; acetonitrile; 11.1: |Horner-Wadsworth-Emmons Olefination / 11.2: |Horner-Wadsworth-Emmons Olefination / 13.1: |Michael Addition;

DOI:10.1021/jo301425c

upstream raw materials:

((2S,4S,6S)-6-(benzyloxy)-4-methoxy-2-methylnonyloxy)(tert-butyl)diphenylsilane

(2S,4S,6S)-6-(benzyloxy)-4-methoxy-2-methylnonan-1-ol

(3R,5S,7S)-7-(benzyloxy)-5-methoxy-3-methyldecanenitrile

(3S)-5-benzyloxy-3-(tert-butyldimethylsilyl)oxypentanal