(2R,3S)-2-[(S)-1-benzyloxypropan-2-yl]-6-methoxy-3-methyl-3,6-dihydro-2H-pyran

Base Information

• Chemical Name: (2R,3S)-2-[(S)-1-benzyloxypropan-2-yl]-6-methoxy-3-methyl-3,6-dihydro-2H-pyran
• CAS No.: 876954-50-6
• Molecular Formula: C₁₇H₂₄O₃
• Molecular Weight: 276.376
• Mol file: 876954-50-6.mol

Synonyms:(2R,3S)-2-[(S)-1-benzyloxypropan-2-yl]-6-methoxy-3-methyl-3,6-dihydro-2H-pyran

Chemical Property of (2R,3S)-2-[(S)-1-benzyloxypropan-2-yl]-6-methoxy-3-methyl-3,6-dihydro-2H-pyran

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S)-2-[(S)-1-benzyloxypropan-2-yl]-6-methoxy-3-methyl-3,6-dihydro-2H-pyran

There total 4 articles about (2R,3S)-2-[(S)-1-benzyloxypropan-2-yl]-6-methoxy-3-methyl-3,6-dihydro-2H-pyran 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:

(5S,6R)-6-[(1S)-2-benzyloxy-1-methyl-ethyl]-5-methyl-5,6-dihydro-pyran-2-one (876954-53-9) → (2R,3S)-2-[(S)-1-benzyloxypropan-2-yl]-6-methoxy-3-methyl-3,6-dihydro-2H-pyran (876954-50-6)

Guidance literature:

Multi-step reaction with 2 steps

1: DIBALH / hexane; CH₂Cl₂ / 0.83 h / -78 °C

2: PPTS / 2 h / 20 °C

With pyridinium p-toluenesulfonate; diisobutylaluminium hydride; In hexane; dichloromethane;

DOI:10.1021/ol052900w

Reference yield:

(S)-N-[(2R,3S,4S)-5-benzyloxy-3-tert-butyldimethylsilyloxy-2,4-dimethylpentanoyl]-4-isopropyl-1,3-thiazolidine-2-thione (876954-51-7) → (2R,3S)-2-[(S)-1-benzyloxypropan-2-yl]-6-methoxy-3-methyl-3,6-dihydro-2H-pyran (876954-50-6)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 93 percent / DIBALH / hexane; CH₂Cl₂ / 0.17 h / -78 °C

2.1: 18-crown-6; K₂CO₃ / toluene / 4 h / -20 - 0 °C

2.2: 176 mg / aq. HCl / methanol / 15 h / 20 °C

3.1: DIBALH / hexane; CH₂Cl₂ / 0.83 h / -78 °C

4.1: PPTS / 2 h / 20 °C

With 18-crown-6 ether; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; potassium carbonate; In hexane; dichloromethane; toluene;

DOI:10.1021/ol052900w

Reference yield:

(2S,3R,4S)-5-benzyloxy-3-(tert-butyldimethylsilyloxy)-2,4-dimethyl-pentanal (444109-42-6) → (2R,3S)-2-[(S)-1-benzyloxypropan-2-yl]-6-methoxy-3-methyl-3,6-dihydro-2H-pyran (876954-50-6)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 18-crown-6; K₂CO₃ / toluene / 4 h / -20 - 0 °C

1.2: 176 mg / aq. HCl / methanol / 15 h / 20 °C

2.1: DIBALH / hexane; CH₂Cl₂ / 0.83 h / -78 °C

3.1: PPTS / 2 h / 20 °C

With 18-crown-6 ether; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; potassium carbonate; In hexane; dichloromethane; toluene;

DOI:10.1021/ol052900w

upstream raw materials:

(5S,6R)-6-((S)-2-Benzyloxy-1-methyl-ethyl)-5-methyl-5,6-dihydro-2H-pyran-2-ol

methanol

(5S,6R)-6-[(1S)-2-benzyloxy-1-methyl-ethyl]-5-methyl-5,6-dihydro-pyran-2-one

(S)-N-[(2R,3S,4S)-5-benzyloxy-3-tert-butyldimethylsilyloxy-2,4-dimethylpentanoyl]-4-isopropyl-1,3-thiazolidine-2-thione

Downstream raw materials:

(R)-2-[(2R,5S,6R)-6-((S)-2-Benzyloxy-1-methyl-ethyl)-5-methyl-5,6-dihydro-2H-pyran-2-yl]-1-((S)-4-isopropyl-2-thioxo-thiazolidin-3-yl)-butan-1-one

(R)-methyl 2-[(2R,5S,6R)-6-[(S)-1-benzyloxypropan-2-yl]-5-methyl-5,6-dihydro-2H-pyran-2-yl]butanoate