N-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-2-[(5S)-4-oxo-2,2-bis(trifluoromethyl)-1,3-dioxolan-5-yl]acetamide

Base Information

• Chemical Name: N-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-2-[(5S)-4-oxo-2,2-bis(trifluoromethyl)-1,3-dioxolan-5-yl]acetamide
• CAS No.: 511309-77-6
• Molecular Formula: C₄₁H₃₉F₆NO₉
• Molecular Weight: 803.752
• Mol file: 511309-77-6.mol

Synonyms:N-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-2-[(5S)-4-oxo-2,2-bis(trifluoromethyl)-1,3-dioxolan-5-yl]acetamide

Chemical Property of N-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-2-[(5S)-4-oxo-2,2-bis(trifluoromethyl)-1,3-dioxolan-5-yl]acetamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-2-[(5S)-4-oxo-2,2-bis(trifluoromethyl)-1,3-dioxolan-5-yl]acetamide

There total 3 articles about N-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-2-[(5S)-4-oxo-2,2-bis(trifluoromethyl)-1,3-dioxolan-5-yl]acetamide 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: 79.0%

1-amino-2,3,4,6-tetra-O-benzyl-1-deoxy-β-D-glucopyranose (4132-27-8,85917-83-5,150370-50-6) + ((5S)-2,2-bis-(trifluoromethyl)-4-oxo-1,3-dioxolan-5-yl)-acetyl chloride (172540-28-2) → N-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-2-[(5S)-4-oxo-2,2-bis(trifluoromethyl)-1,3-dioxolan-5-yl]acetamide (511309-77-6)

Guidance literature:

With pyridine; In dichloromethane; at 0 ℃; for 1.5h;

DOI:10.1007/s00706-004-0187-5

Reference yield:

1-amino-2,3,4,6-tetra-O-benzyl-1-deoxy-β-D-glucopyranose (4132-27-8,85917-83-5,150370-50-6) + ((S)-5-Oxo-2,2-bis-trifluoromethyl-[1,3]dioxolan-4-yl)-acetyl fluoride (511309-73-2) → N-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-2-[(5S)-4-oxo-2,2-bis(trifluoromethyl)-1,3-dioxolan-5-yl]acetamide (511309-77-6)

Guidance literature:

With pyridine; In dichloromethane; at 0 ℃;

DOI:10.1016/S0040-4039(02)02285-2

Reference yield:

[(5S)-2,2-Bis(trifluoromethyl)-4-oxo-1,3-dioxolan-5-yl] acetic acid (172540-27-1) → N-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-2-[(5S)-4-oxo-2,2-bis(trifluoromethyl)-1,3-dioxolan-5-yl]acetamide (511309-77-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 75 percent / DAST / CH₂Cl₂ / 0 °C

2: pyridine / CH₂Cl₂ / 0 °C

With pyridine; 4,4'-diaminostilbene-2,2'-disulfonic acid; In dichloromethane;

DOI:10.1016/S0040-4039(02)02285-2

upstream raw materials:

1-amino-2,3,4,6-tetra-O-benzyl-1-deoxy-β-D-glucopyranose

((S)-5-Oxo-2,2-bis-trifluoromethyl-[1,3]dioxolan-4-yl)-acetyl fluoride

((5S)-2,2-bis-(trifluoromethyl)-4-oxo-1,3-dioxolan-5-yl)-acetyl chloride

[(5S)-2,2-Bis(trifluoromethyl)-4-oxo-1,3-dioxolan-5-yl] acetic acid