8-azido-3,6-dioxaoctyl 2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside

Base Information

• Chemical Name: 8-azido-3,6-dioxaoctyl 2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside
• CAS No.: 106294-96-6
• Molecular Formula: C₂₁H₃₀N₄O₈
• Molecular Weight: 466.491
• Mol file: 106294-96-6.mol

Synonyms:8-azido-3,6-dioxaoctyl 2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside

Chemical Property of 8-azido-3,6-dioxaoctyl 2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 8-azido-3,6-dioxaoctyl 2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside

There total 7 articles about 8-azido-3,6-dioxaoctyl 2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside 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: 82.0%

benzaldehyde dimethyl acetal (1125-88-8) + 8-azido-3,6-dioxaoctyl 2-acetamido-2-deoxy-β-D-glucopyranoside (86520-54-9) → 8-azido-3,6-dioxaoctyl 2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside (106294-96-6)

Guidance literature:

With toluene-4-sulfonic acid; In N,N-dimethyl-formamide;

DOI:10.1016/0008-6215(86)80016-7

Reference yield:

C14H26N4O8 + benzaldehyde dimethyl acetal (1125-88-8) → 8-azido-3,6-dioxaoctyl 2-acetamido-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside + 8-azido-3,6-dioxaoctyl 2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside (106294-96-6)

Guidance literature:

With camphor-10-sulfonic acid; In acetonitrile; at 20 ℃; for 14h;

DOI:10.1002/ejoc.200700322

Reference yield:

2-[2-(2-azidoethoxy)ethoxy]ethanol (86520-52-7) → 8-azido-3,6-dioxaoctyl 2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside (106294-96-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 90 percent / silver triflate, tetramethylurea / CH₂Cl₂ / 20 h / Ambient temperature

2: 76 percent / M sodium methoxide / methanol / 2 h / Ambient temperature

3: 82 percent / p-toluenesulfonic acid monohydrate / dimethylformamide

With sodium methylate; silver trifluoromethanesulfonate; toluene-4-sulfonic acid; tetramethylurea; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/0008-6215(86)80016-7

upstream raw materials:

benzaldehyde dimethyl acetal

8-azido-3,6-dioxaoctyl 2-acetamido-2-deoxy-β-D-glucopyranoside

2-[2-(2-azidoethoxy)ethoxy]ethanol

8-tosyloxy-3,6-dioxaoctanol

Downstream raw materials:

8-azido-3,6-dioxaoctyl 2-acetamido-3-O-benzyl-2-deoxy-β-D-glucopyranoside

8-azido-3,6-dioxaoctyl 3-O-benzyl-2-deoxy-6-O-<2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-gglucopyranosyl>-β-D-glucopyrnoside

8-azido-3,6-dioxaoctyl 2-acetamido-6-O-benzyl-3-O-(3-O-benzyl-β-D-galactopyranosyl-(R)-P-4,6-cyclic 2,2,2-trichloroethyl phosphate)-2-deoxy-β-D-glucopyranoside

8-azido-3,6-dioxaoctyl 2-acetamido-6-O-benzyl-3-O-(3-O-benzyl-β-D-galactopyranosyl-(S)-P-4,6-cyclic 2,2,2-trichloroethyl phosphate)-2-deoxy-β-D-glucopyranoside