(3R,4S,5R)-3-Benzyloxymethyl-5-((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyloxy)-4-methyl-dihydro-furan-2-one

Base Information

• Chemical Name: (3R,4S,5R)-3-Benzyloxymethyl-5-((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyloxy)-4-methyl-dihydro-furan-2-one
• CAS No.: 198277-31-5
• Molecular Formula: C₂₃H₃₄O₄
• Molecular Weight: 374.521
• Mol file: 198277-31-5.mol

Synonyms:(3R,4S,5R)-3-Benzyloxymethyl-5-((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyloxy)-4-methyl-dihydro-furan-2-one

Chemical Property of (3R,4S,5R)-3-Benzyloxymethyl-5-((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyloxy)-4-methyl-dihydro-furan-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,4S,5R)-3-Benzyloxymethyl-5-((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyloxy)-4-methyl-dihydro-furan-2-one

There total 1 articles about (3R,4S,5R)-3-Benzyloxymethyl-5-((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyloxy)-4-methyl-dihydro-furan-2-one 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: 95.0%

Benzyloxymethyl chloride (3587-60-8) + (4S,5R)-5-((1R,2S,5R)-2-Isopropyl-5-methyl-cyclohexyloxy)-4-methyl-dihydro-furan-2-one (120263-02-7) → (3R,4S,5R)-3-Benzyloxymethyl-5-((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyloxy)-4-methyl-dihydro-furan-2-one (198277-31-5)

Guidance literature:

With lithium diisopropyl amide; In tetrahydrofuran; for 12h; -78 deg C up to RT;

DOI:10.1055/s-1997-979

Reference yield: 82.0%

(3R,4S,5R)-3-Benzyloxymethyl-5-((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyloxy)-4-methyl-dihydro-furan-2-one (198277-31-5) → (2S,3S)-2-Benzyloxymethyl-3-methyl-butane-1,4-diol (198277-34-8)

Guidance literature:

With diisobutylaluminium hydride; In tetrahydrofuran; for 12h; Ambient temperature;

DOI:10.1055/s-1997-979

Reference yield:

(3R,4S,5R)-3-Benzyloxymethyl-5-((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyloxy)-4-methyl-dihydro-furan-2-one (198277-31-5) → Toluene-4-sulfonic acid (2S,3R)-6-[1,3]dioxolan-2-yl-3-methyl-2-vinyl-hexyl ester

Guidance literature:

Multi-step reaction with 11 steps

1: 82 percent / DIBAL / tetrahydrofuran / 12 h / Ambient temperature

2: 82 percent / SAM II lipase / 12 h / Ambient temperature

3: imidazole, Et₃N / CH₂Cl₂ / 14 h / Ambient temperature

4: K₂CO₃ / methanol / 4 h / Ambient temperature

5: SO₃*pyridine, DMSO, Et₃N / CH₂Cl₂ / 5 h / -5 °C

6: n-BuLi / tetrahydrofuran / 2.5 h / -78 deg C up to RT

7: 94 percent / H₂ / Raney-Ni / ethanol / 80 °C

8: tetrapropyl ammoniumperruthenate, N-methylmorpholine N-oxide / CH₂Cl₂; acetonitrile / 12 h / Ambient temperature; 4 Angstroem molecular sieves

9: tetrahydrofuran / 12 h / -78 deg C up to RT

10: TBAF / tetrahydrofuran / 4 h / Ambient temperature

11: Et₃N, DMAP / CH₂Cl₂ / 12 h / Ambient temperature

With 1H-imidazole; dmap; n-butyllithium; tetrapropylammonium perruthennate; pyridine-SO₃ complex; SAM II lipase; tetrabutyl ammonium fluoride; hydrogen; diisobutylaluminium hydride; potassium carbonate; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; nickel; In tetrahydrofuran; methanol; ethanol; dichloromethane; acetonitrile;

DOI:10.1055/s-1997-979

upstream raw materials:

Benzyloxymethyl chloride

(4S,5R)-5-((1R,2S,5R)-2-Isopropyl-5-methyl-cyclohexyloxy)-4-methyl-dihydro-furan-2-one

Downstream raw materials:

(2S,3S)-2-Benzyloxymethyl-3-methyl-butane-1,4-diol

(2S,3R)-3-Benzyloxymethyl-4-(tert-butyl-dimethyl-silanyloxy)-2-methyl-butan-1-ol

Acetic acid (2S,3S)-4-benzyloxy-3-hydroxymethyl-2-methyl-butyl ester

((Z)-(2R,3R)-2-Benzyloxymethyl-6-[1,3]dioxolan-2-yl-3-methyl-hex-4-enyloxy)-tert-butyl-dimethyl-silane