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

Base Information

• Chemical Name: tert-butyl 5,6-bis(benzyloxymethyl)-7-((tert-butyldimethylsilyloxy)methyl)bicyclo[2.2.1]hept-2-en-7-ylcarbamate
• CAS No.: 1259807-12-9
• Molecular Formula: C₃₅H₅₁NO₅Si
• Molecular Weight: 593.879
• Mol file: 1259807-12-9.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 4 articles about tert-butyl 5,6-bis(benzyloxymethyl)-7-((tert-butyldimethylsilyloxy)methyl)bicyclo[2.2.1]hept-2-en-7-ylcarbamate 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:

2-benzyloxy-1-methylpyridinium triflate (882980-43-0) + tert-butyl 5,6-bis(hydroxymethyl)-7-((tert-butyldi-methylsilyloxy)methyl)bicyclo[2.2.1]hept-2-en-7-ylcarbamate (1259807-29-8) → tert-butyl 5,6-bis(benzyloxymethyl)-7-((tert-butyldimethylsilyloxy)methyl)bicyclo[2.2.1]hept-2-en-7-ylcarbamate (1259807-12-9)

Guidance literature:

With magnesium oxide; In α,α,α-trifluorotoluene; at 80 ℃; for 24h; Inert atmosphere;

DOI:10.1021/ol102577q

Reference yield:

t-butyldimethylsiyl triflate (69739-34-0) → 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

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

upstream raw materials:

2-benzyloxy-1-methylpyridinium triflate

tert-butyl 5,6-bis(hydroxymethyl)-7-((tert-butyldi-methylsilyloxy)methyl)bicyclo[2.2.1]hept-2-en-7-ylcarbamate

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

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