N^γ-(5-triisopropylsilyl-2,3-di-O-benzyl-α-D-ribosyl)-N^α-benzyloxycarbonylasparagine benzyl ester

Base Information

• Chemical Name: N^γ-(5-triisopropylsilyl-2,3-di-O-benzyl-α-D-ribosyl)-N^α-benzyloxycarbonylasparagine benzyl ester
• CAS No.: 1430197-60-6
• Molecular Formula: C₄₇H₆₀N₂O₉Si
• Molecular Weight: 825.087
• Mol file: 1430197-60-6.mol

Synonyms:N^γ-(5-triisopropylsilyl-2,3-di-O-benzyl-α-D-ribosyl)-N^α-benzyloxycarbonylasparagine benzyl ester

Chemical Property of N^γ-(5-triisopropylsilyl-2,3-di-O-benzyl-α-D-ribosyl)-N^α-benzyloxycarbonylasparagine benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N^γ-(5-triisopropylsilyl-2,3-di-O-benzyl-α-D-ribosyl)-N^α-benzyloxycarbonylasparagine benzyl ester

There total 3 articles about N^γ-(5-triisopropylsilyl-2,3-di-O-benzyl-α-D-ribosyl)-N^α-benzyloxycarbonylasparagine benzyl 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: 68.0%

benzyl Nα-benzyloxycarbonyl-L-asparaginate (4668-39-7) + (N-phenyl)-2,2,2-trifluoroacetimido-5-triisopropylsilyl-2,3-O-benzyl-α,β-D-ribofuranose → Nγ-(5-triisopropylsilyl-2,3-di-O-benzyl-α-D-ribosyl)-Nα-benzyloxycarbonylasparagine benzyl ester (1430197-60-6)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -20 - 20 ℃; stereoselective reaction; Molecular sieve; Inert atmosphere;

DOI:10.1021/ol400929c

Reference yield:

5-triisopropylsilyl-2,3-O-benzyl-D-ribose → Nγ-(5-triisopropylsilyl-2,3-di-O-benzyl-α-D-ribosyl)-Nα-benzyloxycarbonylasparagine benzyl ester (1430197-60-6)

Guidance literature:

Multi-step reaction with 2 steps

1: caesium carbonate / acetone; water / 16 h / 20 °C

2: trimethylsilyl trifluoromethanesulfonate / dichloromethane / -20 - 20 °C / Molecular sieve; Inert atmosphere

With trimethylsilyl trifluoromethanesulfonate; caesium carbonate; In dichloromethane; water; acetone;

DOI:10.1021/ol400929c

Reference yield:

allyl 5-triisopropylsilyl-2,3-bis-O-benzyl-α,β-D-ribofuranoside → Nγ-(5-triisopropylsilyl-2,3-di-O-benzyl-α-D-ribosyl)-Nα-benzyloxycarbonylasparagine benzyl ester (1430197-60-6)

Guidance literature:

Multi-step reaction with 3 steps

1: (1,5-cyclooctadiene)[bis(methyldiphenylphosphine)]iridium(I) hexafluorophosphate; hydrogen / tetrahydrofuran / 1 h / 20 °C / Molecular sieve; Inert atmosphere

2: caesium carbonate / acetone; water / 16 h / 20 °C

3: trimethylsilyl trifluoromethanesulfonate / dichloromethane / -20 - 20 °C / Molecular sieve; Inert atmosphere

With (1,5-cyclooctadiene)[bis(methyldiphenylphosphine)]iridium(I) hexafluorophosphate; trimethylsilyl trifluoromethanesulfonate; hydrogen; caesium carbonate; In tetrahydrofuran; dichloromethane; water; acetone;

DOI:10.1021/ol400929c

upstream raw materials:

benzyl N^α-benzyloxycarbonyl-L-asparaginate

Refernces