3,4,6-Tri-O-benzyl-2-deoxy-α-D-glucopyranosyl trichloroacetamidate

Base Information

• Chemical Name: 3,4,6-Tri-O-benzyl-2-deoxy-α-D-glucopyranosyl trichloroacetamidate
• CAS No.: 220284-26-4
• Molecular Formula: C₂₉H₃₀Cl₃NO₅
• Molecular Weight: 578.92
• Mol file: 220284-26-4.mol

Synonyms:3,4,6-Tri-O-benzyl-2-deoxy-α-D-glucopyranosyl trichloroacetamidate

Chemical Property of 3,4,6-Tri-O-benzyl-2-deoxy-α-D-glucopyranosyl trichloroacetamidate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3,4,6-Tri-O-benzyl-2-deoxy-α-D-glucopyranosyl trichloroacetamidate

There total 2 articles about 3,4,6-Tri-O-benzyl-2-deoxy-α-D-glucopyranosyl trichloroacetamidate 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: 97.0%

3,4,6-tri-O-benzyl-2-deoxy-D-glucopyranose (160549-11-1) + trichloroacetonitrile (545-06-2) → 3,4,6-Tri-O-benzyl-2-deoxy-α-D-glucopyranosyl trichloroacetamidate (220284-26-4)

Guidance literature:

With sodium hydride; In dichloromethane; at 20 ℃; for 1h; Inert atmosphere;

DOI:10.1080/07328303.2014.927882

Reference yield:

3,4,6-tri-O-benzyl-2-deoxy-D-glucopyranose (160549-11-1) + trichloroacetonitrile (545-06-2) → 3,4,6-Tri-O-benzyl-2-deoxy-β-D-glucopyranosyl trichloroacetamidate + 3,4,6-Tri-O-benzyl-2-deoxy-α-D-glucopyranosyl trichloroacetamidate (220284-26-4)

Guidance literature:

With potassium carbonate; In dichloromethane; at 3 ℃; for 4h; Overall yield = 82 %; Overall yield = 239 mg; Inert atmosphere;

DOI:10.1080/07328303.2014.927882

Reference yield: 87.0%

methyl 2-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside (76375-66-1) + 3,4,6-Tri-O-benzyl-2-deoxy-α-D-glucopyranosyl trichloroacetamidate (220284-26-4) → methyl (3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1→3)-2-O-benzyl-4,6-O-benzylidine-α-D-glucopyranoside (1309355-92-7)

Guidance literature:

With iron(III) chloride; In dichloromethane; at -60 - 20 ℃; for 0.666667h; Inert atmosphere; Molecular sieve;

DOI:10.1039/c6ra21859h

upstream raw materials:

3,4,6-tri-O-benzyl-2-deoxy-D-glucopyranose

trichloroacetonitrile

Downstream raw materials:

methyl (3,4,6-tri-O-benzyl-2-deoxy-β-D-arabino-hexopyranosyl)-(1->6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside

methyl 2,3,4-tri-O-benzyl-6-O-(3,4,6-tri-O-benzyl-2-deoxy-α-D-arabino-hexopyranosyl)-α-D-glucopyranoside

O-(3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)-(1[*]6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose

(3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1→6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranoside