(+)-4-[(3S)-methyl-(5R)-(3-phenyl-prop-2-ynyl)tetrahydrofuran-(2S)-yl]butan-1-ol

Base Information

• Chemical Name: (+)-4-[(3S)-methyl-(5R)-(3-phenyl-prop-2-ynyl)tetrahydrofuran-(2S)-yl]butan-1-ol
• CAS No.: 662168-53-8
• Molecular Formula: C₁₈H₂₄O₂
• Molecular Weight: 272.387
• Mol file: 662168-53-8.mol

Synonyms:(+)-4-[(3S)-methyl-(5R)-(3-phenyl-prop-2-ynyl)tetrahydrofuran-(2S)-yl]butan-1-ol

Chemical Property of (+)-4-[(3S)-methyl-(5R)-(3-phenyl-prop-2-ynyl)tetrahydrofuran-(2S)-yl]butan-1-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+)-4-[(3S)-methyl-(5R)-(3-phenyl-prop-2-ynyl)tetrahydrofuran-(2S)-yl]butan-1-ol

There total 1 articles about (+)-4-[(3S)-methyl-(5R)-(3-phenyl-prop-2-ynyl)tetrahydrofuran-(2S)-yl]butan-1-ol 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: 41.0%

trimethyl(phenyl)(1-phenyl-1,2-propadienyl)silane (71321-00-1) + (5S)-[4-(tert-butyldimethylsilanyloxy)butyl]-(4S)-methyltetrahydrofuran-2-ol (662168-52-7) → (+)-4-[(3S)-methyl-(5R)-(3-phenyl-prop-2-ynyl)tetrahydrofuran-(2S)-yl]butan-1-ol (662168-53-8)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at -78 - 23 ℃; for 16h;

DOI:10.1021/ja042733f

Reference yield: 73.0%

(+)-4-[(3S)-methyl-(5R)-(3-phenyl-prop-2-ynyl)tetrahydrofuran-(2S)-yl]butan-1-ol (662168-53-8) → (+)-(2S)-(4-iodobutyl)-(3S)-methyl-(5R)-(3-phenylprop-2-ynyl)tetrahydrofuran (662168-61-8)

Guidance literature:

With 1H-imidazole; iodine; triphenylphosphine; In diethyl ether; acetonitrile; at 0 ℃; for 3.5h;

DOI:10.1021/ja042733f

Reference yield:

(+)-4-[(3S)-methyl-(5R)-(3-phenyl-prop-2-ynyl)tetrahydrofuran-(2S)-yl]butan-1-ol (662168-53-8) → (+)-(2S)-methyl-6-[(3S)-methyl-(5R)-(3-phenylprop-2-ynyl)tetrahydrofuran-(2S)-yl]hexanoic acid (662168-54-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 73 percent / imidazole; PPh₃; iodine / acetonitrile; diethyl ether / 3.5 h / 0 °C

2.1: LiCl; LDA / tetrahydrofuran; hexane / 1.33 h / -78 - 20 °C

2.2: tetrahydrofuran; hexane / 5 h / 0 °C

3.1: 298 mg / aq. NaOH / 2-methyl-propan-2-ol; methanol / 48 h / Heating

With 1H-imidazole; sodium hydroxide; iodine; triphenylphosphine; lithium chloride; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; hexane; acetonitrile; tert-butyl alcohol;

DOI:10.1021/ja042733f

upstream raw materials:

trimethyl(phenyl)(1-phenyl-1,2-propadienyl)silane

(5S)-[4-(tert-butyldimethylsilanyloxy)butyl]-(4S)-methyltetrahydrofuran-2-ol

Downstream raw materials:

(+)-(2S)-(4-iodobutyl)-(3S)-methyl-(5R)-(3-phenylprop-2-ynyl)tetrahydrofuran

(-)-(2S)-methyl-6-[(3S)-methyl-(5R)-(3-phenylprop-2-ynyl)tetrahydrofuran-(2S)-yl]hexanoic acid 3-benzylidene-(5S)-methyl-6-oxo-(1R)-propylhexyl ester

(-)-(2S)-methyl-6-[(3S)-methyl-(5R)-(3-phenylprop-2-ynyl)tetrahydrofuran-(2S)-yl]hexanoic acid 3-benzylidene-6-hydroxy-(5S)-methyl-(1R)-propylhexyl ester

(-)-11,15-dibenzylidene-(14S)-hydroxy-(6S,13R,19R)-trimethyl-(9R)-propyl-8,20-dioxabicyclo[15.2.1]icosan-7-one