(E)-5-(cyclohexylmethyl)-6-hydroxy-5-(hydroxymethyl)hex-2-en-1-yl methyl carbonate

Base Information

• Chemical Name: (E)-5-(cyclohexylmethyl)-6-hydroxy-5-(hydroxymethyl)hex-2-en-1-yl methyl carbonate
• CAS No.: 944164-06-1
• Molecular Formula: C₁₆H₂₈O₅
• Molecular Weight: 300.395
• Mol file: 944164-06-1.mol

Synonyms:(E)-5-(cyclohexylmethyl)-6-hydroxy-5-(hydroxymethyl)hex-2-en-1-yl methyl carbonate

Chemical Property of (E)-5-(cyclohexylmethyl)-6-hydroxy-5-(hydroxymethyl)hex-2-en-1-yl methyl carbonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-5-(cyclohexylmethyl)-6-hydroxy-5-(hydroxymethyl)hex-2-en-1-yl methyl carbonate

There total 4 articles about (E)-5-(cyclohexylmethyl)-6-hydroxy-5-(hydroxymethyl)hex-2-en-1-yl methyl carbonate 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: 56.0%

(E)-5-(cyclohexylmethyl)-5-(hydroxymethyl)hex-2-ene-1,6-diol (944163-88-6) + methyl chloroformate (79-22-1) → (E)-5-(cyclohexylmethyl)-6-hydroxy-5-(hydroxymethyl)hex-2-en-1-yl methyl carbonate (944164-06-1)

Guidance literature:

With pyridine; In dichloromethane; at 0 - 20 ℃;

DOI:10.1002/ejoc.200601019

Reference yield:

2-cyclohexylmethyl-malonic acid dimethyl ester (217654-79-0) → (E)-5-(cyclohexylmethyl)-6-hydroxy-5-(hydroxymethyl)hex-2-en-1-yl methyl carbonate (944164-06-1)

Guidance literature:

Multi-step reaction with 4 steps

1.1: dppb; NaH / Pd₂(dba)3 / tetrahydrofuran / 20 °C

1.2: 77 percent / tetrahydrofuran / 24 h / 20 °C

2.1: 75 percent / LiAlH₄ / diethyl ether / 0.5 h / 20 °C

3.1: 96 percent / Bu₄NF*3H₂O / tetrahydrofuran / 15 h / 20 °C

4.1: 56 percent / pyridine / CH₂Cl₂ / 0 - 20 °C

With pyridine; lithium aluminium tetrahydride; tetrabutyl ammonium fluoride; sodium hydride; 1,4-di(diphenylphosphino)-butane; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; In tetrahydrofuran; diethyl ether; dichloromethane;

DOI:10.1002/ejoc.200601019

Reference yield:

dimethyl {(E)-4-[(tert-butyldimethylsilyl)oxy]but-2-en-1-yl}(cyclohexylmethyl)malonate (944163-58-0) → (E)-5-(cyclohexylmethyl)-6-hydroxy-5-(hydroxymethyl)hex-2-en-1-yl methyl carbonate (944164-06-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 75 percent / LiAlH₄ / diethyl ether / 0.5 h / 20 °C

2: 96 percent / Bu₄NF*3H₂O / tetrahydrofuran / 15 h / 20 °C

3: 56 percent / pyridine / CH₂Cl₂ / 0 - 20 °C

With pyridine; lithium aluminium tetrahydride; tetrabutyl ammonium fluoride; In tetrahydrofuran; diethyl ether; dichloromethane;

DOI:10.1002/ejoc.200601019

upstream raw materials:

(E)-5-(cyclohexylmethyl)-5-(hydroxymethyl)hex-2-ene-1,6-diol

methyl chloroformate

dimethyl {(E)-4-[(tert-butyldimethylsilyl)oxy]but-2-en-1-yl}(cyclohexylmethyl)malonate

2-{(E)-4-[(tert-butyldimethylsilyl)oxy]but-2-en-1-yl}-2-(cyclohexylmethyl)propane-1,3-diol