2-{(4S,5S)-5-[(E)-(3S,5R)-5-(4-Methoxy-benzyloxy)-3-methoxymethoxy-hex-1-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-ethanol

Base Information

• Chemical Name: 2-{(4S,5S)-5-[(E)-(3S,5R)-5-(4-Methoxy-benzyloxy)-3-methoxymethoxy-hex-1-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-ethanol
• CAS No.: 929118-00-3
• Molecular Formula: C₂₃H₃₆O₇
• Molecular Weight: 424.535
• Mol file: 929118-00-3.mol

Synonyms:2-{(4S,5S)-5-[(E)-(3S,5R)-5-(4-Methoxy-benzyloxy)-3-methoxymethoxy-hex-1-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-ethanol

Chemical Property of 2-{(4S,5S)-5-[(E)-(3S,5R)-5-(4-Methoxy-benzyloxy)-3-methoxymethoxy-hex-1-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-ethanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-{(4S,5S)-5-[(E)-(3S,5R)-5-(4-Methoxy-benzyloxy)-3-methoxymethoxy-hex-1-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-ethanol

There total 21 articles about 2-{(4S,5S)-5-[(E)-(3S,5R)-5-(4-Methoxy-benzyloxy)-3-methoxymethoxy-hex-1-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-ethanol 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: 86.0%

(3S,4S,5E,7S,9R)-1-(tert-butyldiphenylsilyloxy)-3.4-(dimethylmethylenedioxy)-9-(4-methoxybenzyloxy)-7-(methoxymethoxy)-5-decene (929117-81-7) → 2-{(4S,5S)-5-[(E)-(3S,5R)-5-(4-Methoxy-benzyloxy)-3-methoxymethoxy-hex-1-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-ethanol (929118-00-3)

Guidance literature:

With tetrabutyl ammonium fluoride;

DOI:10.1021/ol050148t

Reference yield:

(1E)-5-[(tert-butyldiphenylsilyl)oxy]-1-trimethylsilyl-1-penten-3-ol (851278-45-0) → 2-{(4S,5S)-5-[(E)-(3S,5R)-5-(4-Methoxy-benzyloxy)-3-methoxymethoxy-hex-1-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-ethanol (929118-00-3)

Guidance literature:

Multi-step reaction with 10 steps

1.1: 43 percent / t-BuOOH; D-(-)-DIPT; Ti(O-i-Pr)4 / CH₂Cl₂ / 13 h / -20 °C

2.1: Br₂ / CH₂Cl₂ / 0.25 h / cooling

3.1: 1.47 g / Bu₄NF / tetrahydrofuran / 0.25 h / cooling

4.1: MeLi / NiCl₂(dppf) / diethyl ether; tetrahydrofuran / 0.25 h / 0 °C

4.2: 76 percent / diethyl ether; tetrahydrofuran / 20 °C

5.1: 70 percent / NaHCO₃; m-CPBA / CH₂Cl₂ / 0.83 h / 0 °C

6.1: 68 percent / Pd(PPh₃)4 / tetrahydrofuran / 0.5 h / 8 - 11 °C

7.1: PPTS / CH₂Cl₂ / 20 °C

8.1: LiOH / methanol; tetrahydrofuran / 0.5 h / 20 °C

9.1: 134 mg / ethyldiisopropylamine / CH₂Cl₂ / 20 °C

10.1: 86 percent / Bu₄NF / tetrahydrofuran / 2 h / 40 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; lithium hydroxide; tetrabutyl ammonium fluoride; methyllithium; bromine; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; D-(-)-diisopropyl tartrate; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; tetrakis(triphenylphosphine) palladium⁽⁰⁾; [1,1'-bis(diphenylphosphino)ferrocene]nickel(II) chloride; potassium iodide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; 1.1: Sharpless epoxidation;

DOI:10.1021/jo0623890

Reference yield:

(S)-1-chloro-2-hydroxy-5-trimethylsilyl-4-pentyne (148516-13-6) → 2-{(4S,5S)-5-[(E)-(3S,5R)-5-(4-Methoxy-benzyloxy)-3-methoxymethoxy-hex-1-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-ethanol (929118-00-3)

Guidance literature:

Multi-step reaction with 12 steps

1.1: 85 percent / LiAlH₄ / tetrahydrofuran / 4 h / 20 °C

2.1: NaH; NaI / tetrahydrofuran; H₂O; various solvent(s) / 0.5 h / 55 °C

3.1: tetrahydrofuran / 2.5 h / -35 - 20 °C

4.1: tetrahydrofuran / Heating

5.1: 422 mg / tetrahydrofuran / 48 h / 20 °C

6.1: MeLi / NiCl₂(dppf) / diethyl ether; tetrahydrofuran / 0.25 h / 0 °C

6.2: 76 percent / diethyl ether; tetrahydrofuran / 20 °C

7.1: 70 percent / NaHCO₃; m-CPBA / CH₂Cl₂ / 0.83 h / 0 °C

8.1: 68 percent / Pd(PPh₃)4 / tetrahydrofuran / 0.5 h / 8 - 11 °C

9.1: PPTS / CH₂Cl₂ / 20 °C

10.1: LiOH / methanol; tetrahydrofuran / 0.5 h / 20 °C

11.1: 134 mg / ethyldiisopropylamine / CH₂Cl₂ / 20 °C

12.1: 86 percent / Bu₄NF / tetrahydrofuran / 2 h / 40 °C

With lithium hydroxide; lithium aluminium tetrahydride; tetrabutyl ammonium fluoride; methyllithium; pyridinium p-toluenesulfonate; sodium hydride; sodium hydrogencarbonate; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; sodium iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; [1,1'-bis(diphenylphosphino)ferrocene]nickel(II) chloride; potassium iodide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water;

DOI:10.1021/jo0623890

upstream raw materials:

(3S,4S,5E,7S,9R)-1-(tert-butyldiphenylsilyloxy)-3.4-(dimethylmethylenedioxy)-9-(4-methoxybenzyloxy)-7-(methoxymethoxy)-5-decene

(R)-1-methoxy-4-((pent-4-yn-2-yloxy)methyl)benzene

(1'E,4'R)-2-[4'-(4-methoxybenzyloxy)-1'-pentenyl]-5,5-dimethyl-1,3,2-dioxaborinane

(1Z,3S)-1-bromo-5-[(tert-butyldiphenylsilyl)oxy]-1-penten-3-ol

Downstream raw materials:

(3S,4S,5E,7S,9R)-3.4-(dimethylmethylenedioxy)-9-(4-methoxybenzyloxy)-7-(methoxymethoxy)-5-decenal