6′-(R)-methyl-5-O-(5-amino-5,6-dideoxy-β-D-allofuranosyl)-1-N-[(S)-4-amino-2-hydroxy-butanoyl]-paromamine

Base Information

• Chemical Name: 6′-(R)-methyl-5-O-(5-amino-5,6-dideoxy-β-D-allofuranosyl)-1-N-[(S)-4-amino-2-hydroxy-butanoyl]-paromamine
• CAS No.: 1375073-99-6
• Molecular Formula: C₂₃H₄₅N₅O₁₂
• Molecular Weight: 583.637
• Mol file: 1375073-99-6.mol

Synonyms:6′-(R)-methyl-5-O-(5-amino-5,6-dideoxy-β-D-allofuranosyl)-1-N-[(S)-4-amino-2-hydroxy-butanoyl]-paromamine

Chemical Property of 6′-(R)-methyl-5-O-(5-amino-5,6-dideoxy-β-D-allofuranosyl)-1-N-[(S)-4-amino-2-hydroxy-butanoyl]-paromamine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 6′-(R)-methyl-5-O-(5-amino-5,6-dideoxy-β-D-allofuranosyl)-1-N-[(S)-4-amino-2-hydroxy-butanoyl]-paromamine

There total 14 articles about 6′-(R)-methyl-5-O-(5-amino-5,6-dideoxy-β-D-allofuranosyl)-1-N-[(S)-4-amino-2-hydroxy-butanoyl]-paromamine 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: 84.0%

6'-(R)-methyl-5-O-(5-azido-5,6-dideoxy-2,3-O-dibenzoyl-β-d-allofuranosyl)-3',4',6',6-tetra-O-acetyl-2',3-diazido-1-N-[(S)-4-azido-2-O-acetyl-butanoyl]paromamine → 6′-(R)-methyl-5-O-(5-amino-5,6-dideoxy-β-D-allofuranosyl)-1-N-[(S)-4-amino-2-hydroxy-butanoyl]-paromamine (1375073-99-6)

Guidance literature:

6'-(R)-methyl-5-O-(5-azido-5,6-dideoxy-2,3-O-dibenzoyl-β-d-allofuranosyl)-3',4',6',6-tetra-O-acetyl-2',3-diazido-1-N-[(S)-4-azido-2-O-acetyl-butanoyl]paromamine; With ethanol; methylamine; for 8h;

With water; sodium hydroxide; In tetrahydrofuran; at 20 ℃; for 0.166667h;

With trimethylphosphane; In tetrahydrofuran;

Reference yield:

4-methylphenyl 6-deoxy-2,3-O-1-methylethylidene-1-thio-α-L-allofuranoside (1356826-96-4) → 6′-(R)-methyl-5-O-(5-amino-5,6-dideoxy-β-D-allofuranosyl)-1-N-[(S)-4-amino-2-hydroxy-butanoyl]-paromamine (1375073-99-6)

Guidance literature:

Multi-step reaction with 7 steps

1.1: pyridine / dmap / 0 - 20 °C

2.1: N,N,N,N,N,N-hexamethylphosphoric triamide; sodium azide / N,N-dimethyl-formamide / 20 - 70 °C

3.1: water; acetic acid / 70 °C

4.1: pyridine / dmap / 0 - 20 °C

5.1: N-Bromosuccinimide / water; acetone / -30 °C

5.2: 0 °C

6.1: dichloromethane / 0.17 h / -20 °C / 4 ? Molecular sieve

6.2: 1 h / -15 °C

7.1: ethanol; methylamine / 8 h

7.2: 0.17 h / 20 °C

With pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; N-Bromosuccinimide; sodium azide; ethanol; water; acetic acid; methylamine; dmap; In dichloromethane; water; N,N-dimethyl-formamide; acetone;

Reference yield:

4-methylphenyl 6-deoxy-5-O-tosyl-2,3-O-1-methylethylidene-1-thio-α-L-allofuranoside (1356826-99-7) → 6′-(R)-methyl-5-O-(5-amino-5,6-dideoxy-β-D-allofuranosyl)-1-N-[(S)-4-amino-2-hydroxy-butanoyl]-paromamine (1375073-99-6)

Guidance literature:

Multi-step reaction with 6 steps

1.1: N,N,N,N,N,N-hexamethylphosphoric triamide; sodium azide / N,N-dimethyl-formamide / 20 - 70 °C

2.1: water; acetic acid / 70 °C

3.1: pyridine / dmap / 0 - 20 °C

4.1: N-Bromosuccinimide / water; acetone / -30 °C

4.2: 0 °C

5.1: dichloromethane / 0.17 h / -20 °C / 4 ? Molecular sieve

5.2: 1 h / -15 °C

6.1: ethanol; methylamine / 8 h

6.2: 0.17 h / 20 °C

With pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; N-Bromosuccinimide; sodium azide; ethanol; water; acetic acid; methylamine; dmap; In dichloromethane; water; N,N-dimethyl-formamide; acetone;

upstream raw materials:

4-methylphenyl 6-deoxy-2,3-O-1-methylethylidene-1-thio-α-L-allofuranoside

4-methylphenyl 6-deoxy-5-O-tosyl-2,3-O-1-methylethylidene-1-thio-α-L-allofuranoside

4-methylphenyl 5-azido-5,6-dideoxy-2,3-O-1-methylethylidene-1-thio-β-D-allofuranoside

C₁₃H₁₇N₃O₃S