(1R,2S,5R)-5-methyl-2-(propan-2-yl)cyclohexyl (1S,2S)-2-(hydroxymethyl)cyclopropane-1-carboxylate

Base Information

• Chemical Name: (1R,2S,5R)-5-methyl-2-(propan-2-yl)cyclohexyl (1S,2S)-2-(hydroxymethyl)cyclopropane-1-carboxylate
• CAS No.: 329025-40-3
• Molecular Formula: C₁₅H₂₆O₃
• Molecular Weight: 254.37

Synonyms:(1R,2S,5R)-5-methyl-2-(propan-2-yl)cyclohexyl (1S,2S)-2-(hydroxymethyl)cyclopropane-1-carboxylate

Chemical Property of (1R,2S,5R)-5-methyl-2-(propan-2-yl)cyclohexyl (1S,2S)-2-(hydroxymethyl)cyclopropane-1-carboxylate

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Technology Process of (1R,2S,5R)-5-methyl-2-(propan-2-yl)cyclohexyl (1S,2S)-2-(hydroxymethyl)cyclopropane-1-carboxylate

There total 5 articles about (1R,2S,5R)-5-methyl-2-(propan-2-yl)cyclohexyl (1S,2S)-2-(hydroxymethyl)cyclopropane-1-carboxylate 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: 81.0%

(1S,2S)-cyclopropane-1,2-dicarboxylic acid mono-(1R,2S,5R)-(5-isopropyl-2-methyl-cyclohexyl) ester (175221-03-1) → (1R,2S,5R)-5-methyl-2-(propan-2-yl)cyclohexyl (1S,2S)-2-(hydroxymethyl)cyclopropane-1-carboxylate (329025-40-3)

Guidance literature:

With borane-THF; In tetrahydrofuran; at -78 - 20 ℃;

DOI:10.1016/S0957-4166(00)00434-1

Reference yield:

C15H24O4 → (1R,2S,5R)‐2‐isopropyl‐5‐methylcyclohexyl (1R,2R)‐2‐(hydroxymethyl)cyclopropane‐1‐carboxylate + (1R,2S,5R)-5-methyl-2-(propan-2-yl)cyclohexyl (1S,2S)-2-(hydroxymethyl)cyclopropane-1-carboxylate (329025-40-3)

Guidance literature:

With borane-THF; In tetrahydrofuran; at 20 ℃; for 5h; Overall yield = 23.9 mg;

DOI:10.1246/bcsj.20190168

Reference yield:

C17H26O6 → (1R,2S,5R)‐2‐isopropyl‐5‐methylcyclohexyl (1R,2R)‐2‐(hydroxymethyl)cyclopropane‐1‐carboxylate + (1R,2S,5R)-5-methyl-2-(propan-2-yl)cyclohexyl (1S,2S)-2-(hydroxymethyl)cyclopropane-1-carboxylate (329025-40-3)

Guidance literature:

With sodium tetrahydroborate; In methanol; at -78 ℃; for 2h; Overall yield = 66.6 mg;

DOI:10.1246/bcsj.20190168

upstream raw materials:

(1S,2S)-cyclopropane-1,2-dicarboxylic acid mono-(1R,2S,5R)-(5-isopropyl-2-methyl-cyclohexyl) ester

(1S,2S)-cyclopropane-1,2-dicarboxylic acid bis-(1R,2S,5R)-(5-isopropyl-2-methyl-cyclohexyl) ester

bis(1R,2S,5R)-5-methyl-2-(propan-2-yl)cyclohexyl butanedioate

Downstream raw materials:

2-carbomenthyloxy (1S,2S)-cyclopropane-1-carboxaldehyde

(2S,1'S,2'S)-α-(2-carboxycyclopropyl)glycine

(2S,1'S,2'S)-N-[(R)-α-phenylglycinol]-[2'-carbomenthyloxycyclopropyl]-glycinonitrile

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