Phenyl-carbamic acid (2R,3S,4S,5S)-5-isopropyl-2-methoxy-4-methyl-tetrahydro-furan-3-yl ester

Base Information

• Chemical Name: Phenyl-carbamic acid (2R,3S,4S,5S)-5-isopropyl-2-methoxy-4-methyl-tetrahydro-furan-3-yl ester
• CAS No.: 107465-21-4
• Molecular Formula: C₁₆H₂₃NO₄
• Molecular Weight: 293.363

Synonyms:Phenyl-carbamic acid (2R,3S,4S,5S)-5-isopropyl-2-methoxy-4-methyl-tetrahydro-furan-3-yl ester

Chemical Property of Phenyl-carbamic acid (2R,3S,4S,5S)-5-isopropyl-2-methoxy-4-methyl-tetrahydro-furan-3-yl ester

Chemical Property:

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Technology Process of Phenyl-carbamic acid (2R,3S,4S,5S)-5-isopropyl-2-methoxy-4-methyl-tetrahydro-furan-3-yl ester

There total 2 articles about Phenyl-carbamic acid (2R,3S,4S,5S)-5-isopropyl-2-methoxy-4-methyl-tetrahydro-furan-3-yl ester 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: 92.0%

p-chlorphenylisocyanate (104-12-1) + (2R,3S,4R,5S)-5-Isopropyl-2-methoxy-4-methyl-tetrahydro-furan-3-ol (107465-04-3) → Phenyl-carbamic acid (2R,3S,4S,5S)-5-isopropyl-2-methoxy-4-methyl-tetrahydro-furan-3-yl ester (107465-21-4)

Guidance literature:

With pyridine; In dichloromethane; for 48h; Heating;

DOI:10.1016/S0040-4039(00)84858-3

Reference yield:

Diisopropyl-carbamic acid (2S,3R)-3-((1R,2R)-2-hydroxy-1,3-dimethyl-butyl)-oxiranyl ester (107467-85-6,107537-58-6) → Phenyl-carbamic acid (2R,3S,4S,5S)-5-isopropyl-2-methoxy-4-methyl-tetrahydro-furan-3-yl ester (107465-21-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 83 percent / methane sulfonic acid / CH₂Cl₂; methanol / 15 h / -78 °C

2: 92 percent / pyridine / CH₂Cl₂ / 48 h / Heating

With pyridine; methanesulfonic acid; In methanol; dichloromethane;

DOI:10.1016/S0040-4039(00)84858-3

Reference yield: 84.0%

Phenyl-carbamic acid (2R,3S,4S,5S)-5-isopropyl-2-methoxy-4-methyl-tetrahydro-furan-3-yl ester (107465-21-4) → Phenyl-carbamic acid (3S,4S,5S)-5-isopropyl-4-methyl-2-oxo-tetrahydro-furan-3-yl ester (107465-09-8)

Guidance literature:

With boron trifluoride diethyl etherate; 3-chlorobenzoate;

DOI:10.1016/S0040-4039(00)84858-3

upstream raw materials:

p-chlorphenylisocyanate

(2R,3S,4R,5S)-5-Isopropyl-2-methoxy-4-methyl-tetrahydro-furan-3-ol

Diisopropyl-carbamic acid (2S,3R)-3-((1R,2R)-2-hydroxy-1,3-dimethyl-butyl)-oxiranyl ester

Downstream raw materials:

Phenyl-carbamic acid (3S,4S,5S)-5-isopropyl-4-methyl-2-oxo-tetrahydro-furan-3-yl ester

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