2-((1S,2R,5S)-2-isopropyl-5-methylcyclohexyl) 3-methyl (1R,2S,3S,4S,7R)-7-(tertbutoxycarbonylamino)-7-(hydroxymethyl)bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylate

Base Information

• Chemical Name: 2-((1S,2R,5S)-2-isopropyl-5-methylcyclohexyl) 3-methyl (1R,2S,3S,4S,7R)-7-(tertbutoxycarbonylamino)-7-(hydroxymethyl)bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylate
• CAS No.: 1259807-08-3
• Molecular Formula: C₂₆H₄₁NO₇
• Molecular Weight: 479.614
• Mol file: 1259807-08-3.mol

Synonyms:2-((1S,2R,5S)-2-isopropyl-5-methylcyclohexyl) 3-methyl (1R,2S,3S,4S,7R)-7-(tertbutoxycarbonylamino)-7-(hydroxymethyl)bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylate

Chemical Property of 2-((1S,2R,5S)-2-isopropyl-5-methylcyclohexyl) 3-methyl (1R,2S,3S,4S,7R)-7-(tertbutoxycarbonylamino)-7-(hydroxymethyl)bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-((1S,2R,5S)-2-isopropyl-5-methylcyclohexyl) 3-methyl (1R,2S,3S,4S,7R)-7-(tertbutoxycarbonylamino)-7-(hydroxymethyl)bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylate

There total 1 articles about 2-((1S,2R,5S)-2-isopropyl-5-methylcyclohexyl) 3-methyl (1R,2S,3S,4S,7R)-7-(tertbutoxycarbonylamino)-7-(hydroxymethyl)bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylate 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: 87.0%

C32H42N4O7 → 2-((1S,2R,5S)-2-isopropyl-5-methylcyclohexyl) 3-methyl (1R,2S,3S,4S,7R)-7-(tertbutoxycarbonylamino)-7-(hydroxymethyl)bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylate (1259807-08-3)

Guidance literature:

C₃₂H₄₂N₄O₇; With sodium tetrahydroborate; In methanol; at 20 ℃; for 4h; Inert atmosphere;

With ammonium chloride; In methanol; water; Saturated solution;

DOI:10.1021/ol102577q

Reference yield: 94.0%

2-((1S,2R,5S)-2-isopropyl-5-methylcyclohexyl) 3-methyl (1R,2S,3S,4S,7R)-7-(tertbutoxycarbonylamino)-7-(hydroxymethyl)bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylate (1259807-08-3) + t-butyldimethylsiyl triflate (69739-34-0) → 2-((1R,2S,5R)-2-isopropyl-5-methylcyclohexyl) 3-methyl (1R,2S,3S,4S,7R)-7-(tertbutoxycarbonylamino)-7-((tert-butyldimethylsilyloxy)methyl)bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylate (1259807-09-4)

Guidance literature:

With 1-methyl-1H-imidazole; In dichloromethane; at 0 ℃; for 1h; Inert atmosphere;

DOI:10.1021/ol102577q

Reference yield:

2-((1S,2R,5S)-2-isopropyl-5-methylcyclohexyl) 3-methyl (1R,2S,3S,4S,7R)-7-(tertbutoxycarbonylamino)-7-(hydroxymethyl)bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylate (1259807-08-3) → tert-butyl 5,6-bis(benzyloxymethyl)-7-((tert-butyldimethylsilyloxy)methyl)bicyclo[2.2.1]hept-2-en-7-ylcarbamate (1259807-12-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 1-methyl-1H-imidazole / dichloromethane / 1 h / 0 °C / Inert atmosphere

2: lithium borohydride / tetrahydrofuran / 20 - 40 °C / Inert atmosphere

3: magnesium oxide / α,α,α-trifluorotoluene / 24 h / 80 °C / Inert atmosphere

With 1-methyl-1H-imidazole; lithium borohydride; magnesium oxide; In tetrahydrofuran; dichloromethane; α,α,α-trifluorotoluene;

DOI:10.1021/ol102577q

Downstream raw materials:

tert-butyl 5,6-bis(benzyloxymethyl)-7-((tert-butyldimethylsilyloxy)methyl)bicyclo[2.2.1]hept-2-en-7-ylcarbamate

2-((1R,2S,5R)-2-isopropyl-5-methylcyclohexyl) 3-methyl (1R,2S,3S,4S,7R)-7-(tertbutoxycarbonylamino)-7-((tert-butyldimethylsilyloxy)methyl)bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylate