(1R,2R,3R)-2-(hydroxymethyl)-1-methyl-3-(prop-1-en-2-yl)cyclopentanol

Base Information

• Chemical Name: (1R,2R,3R)-2-(hydroxymethyl)-1-methyl-3-(prop-1-en-2-yl)cyclopentanol
• CAS No.: 1280572-66-8
• Molecular Formula: C₁₀H₁₈O₂
• Molecular Weight: 170.252
• Mol file: 1280572-66-8.mol

Synonyms:(1R,2R,3R)-2-(hydroxymethyl)-1-methyl-3-(prop-1-en-2-yl)cyclopentanol

Chemical Property of (1R,2R,3R)-2-(hydroxymethyl)-1-methyl-3-(prop-1-en-2-yl)cyclopentanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,2R,3R)-2-(hydroxymethyl)-1-methyl-3-(prop-1-en-2-yl)cyclopentanol

There total 1 articles about (1R,2R,3R)-2-(hydroxymethyl)-1-methyl-3-(prop-1-en-2-yl)cyclopentanol 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: 5.0%

(3R)-(-)-3,7-dimethyl-1,2-epoxy-6-octen-3-ol (443361-64-6) → (3aR,4R,6aS)-1,1,4-trimethylhexahydro-1H-cyclopenta[c]furan-4-ol (1280572-74-8) + (3aS,4R,6aR)-1,1,4-trimethylhexahydro-1H-cyclopenta[c]furan-4-ol (1280572-75-9) + (1R,2R,3S)-2-(hydroxymethyl)-3-isopropyl-1-methylcyclopentanol (1280572-71-5) + (1R,2S,3R)-2-(hydroxymethyl)-3-isopropyl-1-methylcyclopentanol (1280572-72-6) + (1R,2R,3R)-2-(hydroxymethyl)-1-methyl-3-(prop-1-en-2-yl)cyclopentanol (1280572-66-8) + (1R,2S,4S)-1-methyl-4-(prop-1-en-2-yl)cyclohexane-1,2-diol (39903-99-6)

Guidance literature:

With 2,4,6-trimethyl-pyridine; bis(cyclopentadienyl)titanium dichloride; manganese; chloro-trimethyl-silane; In tetrahydrofuran; for 1.5h; Inert atmosphere;

DOI:10.1021/jo102280n

Reference yield: 83.0%

p-Anisaldehyde dimethyl acetal (2186-92-7) + (1R,2R,3R)-2-(hydroxymethyl)-1-methyl-3-(prop-1-en-2-yl)cyclopentanol (1280572-66-8) → (4aR,5R,7aR)-2-(4-methoxyphenyl)-7a-methyl-5-(prop-1-en-2-yl)hexahydrocyclopenta[d][1,3]dioxine

Guidance literature:

With pyridinium p-toluenesulfonate; In dichloromethane; at 0 - 20 ℃; for 4h; Inert atmosphere; Schlenk technique;

DOI:10.1021/acs.orglett.6b00814

Reference yield:

(1R,2R,3R)-2-(hydroxymethyl)-1-methyl-3-(prop-1-en-2-yl)cyclopentanol (1280572-66-8) → 4-((1S,2R,5R)-2-((4-methoxybenzyl)oxy)-2-methyl-5-(prop-1-en-2-yl)cyclopentyl)-3,3-dimethylbutanal

Guidance literature:

Multi-step reaction with 7 steps

1.1: pyridinium p-toluenesulfonate / dichloromethane / 4 h / 0 - 20 °C / Inert atmosphere; Schlenk technique

2.1: diisobutylaluminium hydride / dichloromethane / 1 h / -78 - 0 °C / Inert atmosphere; Schlenk technique

3.1: pyridine / 18 h / 20 °C / Inert atmosphere; Schlenk technique

4.1: tetrahydrofuran / 0.5 h / Inert atmosphere; Schlenk technique; Alkaline conditions

4.2: 0 - 20 °C / Inert atmosphere; Schlenk technique

5.1: diisobutylaluminium hydride / dichloromethane / 1 h / -78 - 0 °C / Inert atmosphere; Schlenk technique

5.2: 0.5 h / Schlenk technique

6.1: potassium hexamethylsilazane / tetrahydrofuran / 0.5 h / Inert atmosphere; Schlenk technique

6.2: 16 h / Inert atmosphere; Schlenk technique

7.1: hydrogenchloride / tetrahydrofuran; water / 2 h / Inert atmosphere; Schlenk technique

With pyridine; hydrogenchloride; pyridinium p-toluenesulfonate; potassium hexamethylsilazane; diisobutylaluminium hydride; In tetrahydrofuran; dichloromethane; water; 6.1: |Horner-Wadsworth-Emmons Olefination / 6.2: |Horner-Wadsworth-Emmons Olefination;

DOI:10.1021/acs.orglett.6b00814

upstream raw materials:

(3R)-(-)-3,7-dimethyl-1,2-epoxy-6-octen-3-ol

Downstream raw materials:

C₂₉H₃₂Br₂O₄

cyclonerodiol