O-(3,4,6-tri-O-benzyl-α-D-glucopyranosyl)-N-(tert-butoxycarbonyl)-L-serine benzyl ester

Base Information

• Chemical Name: O-(3,4,6-tri-O-benzyl-α-D-glucopyranosyl)-N-(tert-butoxycarbonyl)-L-serine benzyl ester
• CAS No.: 1432621-82-3
• Molecular Formula: C₄₉H₅₅NO₁₀
• Molecular Weight: 817.976
• Mol file: 1432621-82-3.mol

Synonyms:O-(3,4,6-tri-O-benzyl-α-D-glucopyranosyl)-N-(tert-butoxycarbonyl)-L-serine benzyl ester

Chemical Property of O-(3,4,6-tri-O-benzyl-α-D-glucopyranosyl)-N-(tert-butoxycarbonyl)-L-serine benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of O-(3,4,6-tri-O-benzyl-α-D-glucopyranosyl)-N-(tert-butoxycarbonyl)-L-serine benzyl ester

There total 3 articles about O-(3,4,6-tri-O-benzyl-α-D-glucopyranosyl)-N-(tert-butoxycarbonyl)-L-serine 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:

phenyl 2,3,4,5-tetra-O-benzyl-1-thio-β-D-glucopyranoside (38184-10-0) + N-tert-butoxycarbonyl-L-serine benzyl ester (59524-02-6) → O-(3,4,6-tri-O-benzyl-α-D-glucopyranosyl)-N-(tert-butoxycarbonyl)-L-serine benzyl ester (1432621-82-3) + O-(3,4,6-tri-O-benzyl-β-D-glucopyranosyl)-N-(tert-butoxycarbonyl)-L-serine benzyl ester (1432621-83-4)

Guidance literature:

phenyl 2,3,4,5-tetra-O-benzyl-1-thio-β-D-glucopyranoside; With N-methylmaleimide; trifluoromethylsulfonic anhydride; 1,1'-sulfinylbisbenzene; 2,4,6-tri-tert-butylpyrimidine; In dichloromethane; at -78 ℃; for 0.0833333h; Molecular sieve; Inert atmosphere;

With tetra-(n-butyl)ammonium iodide; In dichloromethane; at -78 ℃; for 0.166667h;

N-tert-butoxycarbonyl-L-serine benzyl ester; In 1,4-dioxane; dichloromethane; at -78 - 20 ℃; for 18h; Overall yield = 57 %; Overall yield = 34.9 mg;

Reference yield:

Trifluoro-methanesulfonic acid (3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl ester (59964-41-9) → O-(3,4,6-tri-O-benzyl-α-D-glucopyranosyl)-N-(tert-butoxycarbonyl)-L-serine benzyl ester (1432621-82-3) + O-(3,4,6-tri-O-benzyl-β-D-glucopyranosyl)-N-(tert-butoxycarbonyl)-L-serine benzyl ester (1432621-83-4)

Guidance literature:

Multi-step reaction with 2 steps

1: tetra-(n-butyl)ammonium iodide / dichloromethane / 0.17 h / -78 °C / Inert atmosphere

2: dichloromethane; 1,4-dioxane / 18 h / -78 - 20 °C / Inert atmosphere

With tetra-(n-butyl)ammonium iodide; In 1,4-dioxane; dichloromethane;

DOI:10.1021/ol401095k

Reference yield:

phenyl 2,3,4,5-tetra-O-benzyl-1-thio-β-D-glucopyranoside (38184-10-0) → O-(3,4,6-tri-O-benzyl-α-D-glucopyranosyl)-N-(tert-butoxycarbonyl)-L-serine benzyl ester (1432621-82-3) + O-(3,4,6-tri-O-benzyl-β-D-glucopyranosyl)-N-(tert-butoxycarbonyl)-L-serine benzyl ester (1432621-83-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 2,4,6-tri-tert-butylpyrimidine; N-methylmaleimide / dichloromethane / 0.08 h / -78 °C / Inert atmosphere; Molecular sieve

2: tetra-(n-butyl)ammonium iodide / dichloromethane / 0.17 h / -78 °C / Inert atmosphere

3: dichloromethane; 1,4-dioxane / 18 h / -78 - 20 °C / Inert atmosphere

With N-methylmaleimide; tetra-(n-butyl)ammonium iodide; 2,4,6-tri-tert-butylpyrimidine; In 1,4-dioxane; dichloromethane;

DOI:10.1021/ol401095k

upstream raw materials:

phenyl 2,3,4,5-tetra-O-benzyl-1-thio-β-D-glucopyranoside

Trifluoro-methanesulfonic acid (3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl ester

N-tert-butoxycarbonyl-L-serine benzyl ester