(2R,5S)-5-((4-methoxybenzyl)oxy)hexane-1,2-diol

Base Information

• Chemical Name: (2R,5S)-5-((4-methoxybenzyl)oxy)hexane-1,2-diol
• CAS No.: 1039357-63-5
• Molecular Formula: C₁₄H₂₂O₄
• Molecular Weight: 254.326
• Mol file: 1039357-63-5.mol

Synonyms:(2R,5S)-5-((4-methoxybenzyl)oxy)hexane-1,2-diol

Chemical Property of (2R,5S)-5-((4-methoxybenzyl)oxy)hexane-1,2-diol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,5S)-5-((4-methoxybenzyl)oxy)hexane-1,2-diol

There total 3 articles about (2R,5S)-5-((4-methoxybenzyl)oxy)hexane-1,2-diol 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: 87.0%

(S)-1-((hex-5-en-2-yloxy)methyl)-4-methoxybenzene (1039357-62-4) → (2R,5S)-5-((4-methoxybenzyl)oxy)hexane-1,2-diol (1039357-63-5)

Guidance literature:

With AD-mix-β; In water; tert-butyl alcohol; at 0 ℃; for 48h;

DOI:10.1016/j.tetasy.2008.03.024

Reference yield:

(S)-1-((hex-5-en-2-yloxy)methyl)-4-methoxybenzene (1039357-62-4) → (2R,5S)-5-((4-methoxybenzyl)oxy)hexane-1,2-diol (1039357-63-5) + 5-((4-methoxybenzyl)oxy)hexane-1,2-diol

Guidance literature:

With potassium hexachloroosmate(IV); potassium carbonate; potassium hexacyanoferrate(III); hydroquinidine (anthraquinone-1,4-diyl) diether; In water; tert-butyl alcohol; at 0 ℃; for 12h; Overall yield = 95 %; Overall yield = 241.5 mg; Optical yield = 80 %de; Inert atmosphere;

DOI:10.1021/jacs.9b02318

Reference yield:

(S)-5-hexen-2-ol (626-94-8) + p-methoxybenzyl chloride (824-94-2) → (2R,5S)-5-((4-methoxybenzyl)oxy)hexane-1,2-diol (1039357-63-5) + 5-((4-methoxybenzyl)oxy)hexane-1,2-diol

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium hydride / tetrahydrofuran / 0.5 h / 22 °C / Inert atmosphere

1.2: 12 h / 60 °C / Inert atmosphere

2.1: potassium hexacyanoferrate(III); potassium hexachloroosmate(IV); potassium carbonate; hydroquinidine (anthraquinone-1,4-diyl) diether / water; tert-butyl alcohol / 12 h / 0 °C / Inert atmosphere

With potassium hexachloroosmate(IV); sodium hydride; potassium carbonate; potassium hexacyanoferrate(III); hydroquinidine (anthraquinone-1,4-diyl) diether; In tetrahydrofuran; water; tert-butyl alcohol;

DOI:10.1021/jacs.9b02318

upstream raw materials:

(S)-1-((hex-5-en-2-yloxy)methyl)-4-methoxybenzene

(S)-5-hexen-2-ol

p-methoxybenzyl chloride

Downstream raw materials:

C₁₄H₂₀O₃

Refernces

• 1、 Liu, Jian,Zhang, Ling,He, Jinmei,He, Liuer,Ma, Bowen,Pan, Xinfu,She, Xuegong. "Facile total synthesis of the antimalarial nonenolide". . p. 906 - 911. Retrieved 2008/09/21.