N^δ-(5-tert-butyl-diphenylsilyl-2,3-di-O-benzyl-β-D-ribosyl)-N^α-fluorenylmethoxycarbonylglutamine (4-methoxybenzyl) ester

Base Information

• Chemical Name: N^δ-(5-tert-butyl-diphenylsilyl-2,3-di-O-benzyl-β-D-ribosyl)-N^α-fluorenylmethoxycarbonylglutamine (4-methoxybenzyl) ester
• CAS No.: 1430197-86-6
• Molecular Formula: C₆₃H₆₆N₂O₁₀Si
• Molecular Weight: 1039.31
• Mol file: 1430197-86-6.mol

Synonyms:

Chemical Property of N^δ-(5-tert-butyl-diphenylsilyl-2,3-di-O-benzyl-β-D-ribosyl)-N^α-fluorenylmethoxycarbonylglutamine (4-methoxybenzyl) ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N^δ-(5-tert-butyl-diphenylsilyl-2,3-di-O-benzyl-β-D-ribosyl)-N^α-fluorenylmethoxycarbonylglutamine (4-methoxybenzyl) ester

There total 2 articles about N^δ-(5-tert-butyl-diphenylsilyl-2,3-di-O-benzyl-β-D-ribosyl)-N^α-fluorenylmethoxycarbonylglutamine (4-methoxybenzyl) 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:

(N-phenyl)-2,2,2-trifluoroacetimido-5-tert-butyldiphenylsilyl-2,3-O-benzyl-α,β-D-ribofuranose + (S)-Nα-(Fluoren-9-ylmethoxycarbonyl)glutamine 4-methoxybenzyl ester (313944-86-4) → Nδ-(5-tert-butyl-diphenylsilyl-2,3-di-O-benzyl-α-D-ribosyl)-Nα-fluorenylmethoxycarbonylglutamine (4-methoxybenzyl) ester (1430197-64-0) + Nδ-(5-tert-butyl-diphenylsilyl-2,3-di-O-benzyl-β-D-ribosyl)-Nα-fluorenylmethoxycarbonylglutamine (4-methoxybenzyl) ester (1430197-86-6)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In 1,4-dioxane; dichloromethane; at 0 - 20 ℃; Overall yield = 49 %; Overall yield = 95 mg; stereoselective reaction; Molecular sieve; Inert atmosphere;

DOI:10.1021/ol400929c

Reference yield:

5-tert-butyldiphenylsilyl-2,3-O-benzyl-D-ribose → Nδ-(5-tert-butyl-diphenylsilyl-2,3-di-O-benzyl-α-D-ribosyl)-Nα-fluorenylmethoxycarbonylglutamine (4-methoxybenzyl) ester (1430197-64-0) + Nδ-(5-tert-butyl-diphenylsilyl-2,3-di-O-benzyl-β-D-ribosyl)-Nα-fluorenylmethoxycarbonylglutamine (4-methoxybenzyl) ester (1430197-86-6)

Guidance literature:

Multi-step reaction with 2 steps

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

2: trimethylsilyl trifluoromethanesulfonate / dichloromethane; 1,4-dioxane / 0 - 20 °C / Molecular sieve; Inert atmosphere

With trimethylsilyl trifluoromethanesulfonate; caesium carbonate; In 1,4-dioxane; dichloromethane; water; acetone;

DOI:10.1021/ol400929c

upstream raw materials:

(S)-N^α-(Fluoren-9-ylmethoxycarbonyl)glutamine 4-methoxybenzyl ester