3-(2-phenyl-benzo[b]furan-3-yl)-prop-2-ynyl 4-amino-2,3,4,6-tetradeoxy-α-L-threo-hexopyranoside

Base Information

• Chemical Name: 3-(2-phenyl-benzo[b]furan-3-yl)-prop-2-ynyl 4-amino-2,3,4,6-tetradeoxy-α-L-threo-hexopyranoside
• CAS No.: 1192234-92-6
• Molecular Formula: C₂₃H₂₃NO₃
• Molecular Weight: 361.441
• Mol file: 1192234-92-6.mol

Synonyms:3-(2-phenyl-benzo[b]furan-3-yl)-prop-2-ynyl 4-amino-2,3,4,6-tetradeoxy-α-L-threo-hexopyranoside

Chemical Property of 3-(2-phenyl-benzo[b]furan-3-yl)-prop-2-ynyl 4-amino-2,3,4,6-tetradeoxy-α-L-threo-hexopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-(2-phenyl-benzo[b]furan-3-yl)-prop-2-ynyl 4-amino-2,3,4,6-tetradeoxy-α-L-threo-hexopyranoside

There total 3 articles about 3-(2-phenyl-benzo[b]furan-3-yl)-prop-2-ynyl 4-amino-2,3,4,6-tetradeoxy-α-L-threo-hexopyranoside 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: 91.0%

3-(2-phenylbenzo[b]furan-3-yl)prop-2-ynyl 4-azido-2,3,4,6-tetradeoxy-α-L-threo-hexopyranoside (1208260-34-7) → 3-(2-phenyl-benzo[b]furan-3-yl)-prop-2-ynyl 4-amino-2,3,4,6-tetradeoxy-α-L-threo-hexopyranoside (1192234-92-6)

Guidance literature:

With water; triphenylphosphine; In tetrahydrofuran; Reflux; Inert atmosphere;

DOI:10.1016/j.carres.2009.10.010

Reference yield: 85.0%

propargyl 4-amino-2,3,4,6-tetradeoxy-α-L-threo-hexopyranoside (1192235-31-6) + 3-iodo-2-phenylbenzo[b]furan (246230-86-4) → 3-(2-phenyl-benzo[b]furan-3-yl)-prop-2-ynyl 4-amino-2,3,4,6-tetradeoxy-α-L-threo-hexopyranoside (1192234-92-6)

Guidance literature:

With piperidine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; at 20 ℃; Inert atmosphere;

DOI:10.1039/b909153j

Reference yield:

3-(2-phenyl-benzo[b]furan-3-yl)-prop-2-ynyl 4-O-acetyl-2,3,6-trideoxy-α-L-erythro-hexopyranoside (1192235-32-7) → 3-(2-phenyl-benzo[b]furan-3-yl)-prop-2-ynyl 4-amino-2,3,4,6-tetradeoxy-α-L-threo-hexopyranoside (1192234-92-6)

Guidance literature:

Multi-step reaction with 3 steps

1: potassium carbonate / methanol / 20 °C / Inert atmosphere

2: di-isopropyl azodicarboxylate; diphenyl phosphoryl azide; triphenylphosphine / tetrahydrofuran / -20 - 20 °C / Inert atmosphere

3: water; triphenylphosphine / tetrahydrofuran / Reflux; Inert atmosphere

With di-isopropyl azodicarboxylate; diphenyl phosphoryl azide; water; potassium carbonate; triphenylphosphine; In tetrahydrofuran; methanol; 2: Mitsunobu reaction / 3: Staudinger reaction;

DOI:10.1016/j.carres.2009.10.010

upstream raw materials:

propargyl 4-amino-2,3,4,6-tetradeoxy-α-L-threo-hexopyranoside

3-iodo-2-phenylbenzo[b]furan

3-(2-phenyl-benzo[b]furan-3-yl)-prop-2-ynyl 4-O-acetyl-2,3,6-trideoxy-α-L-erythro-hexopyranoside

3-(2-phenylbenzo[b]furan-3-yl)prop-2-ynyl 4-azido-2,3,4,6-tetradeoxy-α-L-threo-hexopyranoside

Downstream raw materials:

3-(2-phenyl-benzo[b]furan-3-yl)-prop-2-ynyl 4-N-acetyl-2,3,4,6-tetradeoxy-α-L-threo-hexopyranoside

3-(2-phenyl-benzo[b]furan-3-yl)-prop-2-ynyl 4-N,N-dibutyl-2,3,4,6-tetradeoxy-α-L-threo-hexopyranoside

3-(2-phenyl-benzo[b]furan-3-yl)-prop-2-ynyl 4-N,N-diethyl-2,3,4,6-tetradeoxy-α-L-threo-hexopyranoside

3-(2-phenyl-benzo[b]furan-3-yl)-prop-2-ynyl 4-N,N-di-(3-methyl)-butyl-2,3,4,6-tetradeoxy-α-L-threo-hexopyranoside