3-O-(5-tert-butoxycarbonylaminopent-1-en-2-yl)-1,5-anhydro-4,6-O-benzylidene-2-deoxy-D-ribo-hex-1-enitol

Base Information

• Chemical Name: 3-O-(5-tert-butoxycarbonylaminopent-1-en-2-yl)-1,5-anhydro-4,6-O-benzylidene-2-deoxy-D-ribo-hex-1-enitol
• CAS No.: 578713-83-4
• Molecular Formula: C₂₃H₃₁NO₆
• Molecular Weight: 417.502

Synonyms:3-O-(5-tert-butoxycarbonylaminopent-1-en-2-yl)-1,5-anhydro-4,6-O-benzylidene-2-deoxy-D-ribo-hex-1-enitol

Chemical Property of 3-O-(5-tert-butoxycarbonylaminopent-1-en-2-yl)-1,5-anhydro-4,6-O-benzylidene-2-deoxy-D-ribo-hex-1-enitol

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Technology Process of 3-O-(5-tert-butoxycarbonylaminopent-1-en-2-yl)-1,5-anhydro-4,6-O-benzylidene-2-deoxy-D-ribo-hex-1-enitol

There total 3 articles about 3-O-(5-tert-butoxycarbonylaminopent-1-en-2-yl)-1,5-anhydro-4,6-O-benzylidene-2-deoxy-D-ribo-hex-1-enitol 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: 93.0%

3-O-(4-butoxycarbonylaminobutanoyl)-1,5-anhydro-4,6-O-benzylidene-2-deoxy-D-ribo-hex-1-enitol (578713-79-8) → 3-O-(5-tert-butoxycarbonylaminopent-1-en-2-yl)-1,5-anhydro-4,6-O-benzylidene-2-deoxy-D-ribo-hex-1-enitol (578713-83-4)

Guidance literature:

With pyridine; In tetrahydrofuran; at -40 ℃; for 1.5h;

DOI:10.1039/b306675b

Reference yield: 93.0%

3-O-(4-butoxycarbonylaminobutanoyl)-1,5-anhydro-4,6-O-benzylidene-2-deoxy-D-ribo-hex-1-enitol (578713-79-8) → 3-O-(5-tert-butoxycarbonylaminopent-1-en-2-yl)-1,5-anhydro-4,6-O-benzylidene-2-deoxy-D-ribo-hex-1-enitol (578713-83-4)

Guidance literature:

With pyridine; In tetrahydrofuran; at -40 ℃;

DOI:10.1016/S0040-4039(03)00710-X

Reference yield:

N-(tert-butoxycarbonyl)-4-aminobutanoic acid (57294-38-9) → 3-O-(5-tert-butoxycarbonylaminopent-1-en-2-yl)-1,5-anhydro-4,6-O-benzylidene-2-deoxy-D-ribo-hex-1-enitol (578713-83-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 92 percent / dicyclohexylcarbodiimide; DMAP / CH₂Cl₂ / 15 h / 20 °C

2: 93 percent / pyridine / tetrahydrofuran / 1.5 h / -40 °C

With pyridine; dmap; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane; 2: Tebbe methylenation;

DOI:10.1039/b306675b

upstream raw materials:

3-O-(4-butoxycarbonylaminobutanoyl)-1,5-anhydro-4,6-O-benzylidene-2-deoxy-D-ribo-hex-1-enitol

N-(tert-butoxycarbonyl)-4-aminobutanoic acid

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