3-C-(3-aminopropyl)-1,6-anhydro-2,4-di-O-tosyl-β-D-allopyranose

Base Information

• Chemical Name: 3-C-(3-aminopropyl)-1,6-anhydro-2,4-di-O-tosyl-β-D-allopyranose
• CAS No.: 916676-59-0
• Molecular Formula: C₂₃H₂₉NO₉S₂
• Molecular Weight: 527.617
• Mol file: 916676-59-0.mol

Synonyms:3-C-(3-aminopropyl)-1,6-anhydro-2,4-di-O-tosyl-β-D-allopyranose

Chemical Property of 3-C-(3-aminopropyl)-1,6-anhydro-2,4-di-O-tosyl-β-D-allopyranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-C-(3-aminopropyl)-1,6-anhydro-2,4-di-O-tosyl-β-D-allopyranose

There total 4 articles about 3-C-(3-aminopropyl)-1,6-anhydro-2,4-di-O-tosyl-β-D-allopyranose 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: 73.0%

1,6-anhydro-3-C-(3-azidopropyl)-2,4-di-O-tosyl-β-D-allopyranose (916676-58-9) → 3-C-(3-aminopropyl)-1,6-anhydro-2,4-di-O-tosyl-β-D-allopyranose (916676-59-0)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; chloroform; acetic acid; at 20 ℃; for 48h;

DOI:10.1135/cccc20051429

Reference yield:

3-C-allyl-1,6-anhydro-2,4-di-O-tosyl-β-D-allopyranose (916676-55-6) → 3-C-(3-aminopropyl)-1,6-anhydro-2,4-di-O-tosyl-β-D-allopyranose (916676-59-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: BH₃ / tetrahydrofuran / 1 h / 20 °C

1.2: 77 percent / H₂O₂; aq. NaOH / tetrahydrofuran / 1 h / 20 °C

2.1: 95 percent / Ph₃P; diisopropyl diazenedicarboxylate; HN₃ / tetrahydrofuran; benzene / 1 h / 20 °C

3.1: 73 percent / H₂ / Pd/C / CHCl₃; methanol; acetic acid / 48 h / 20 °C

With tris-(2-chloro-ethyl)-amine; di-isopropyl azodicarboxylate; borane; hydrogen; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; methanol; chloroform; acetic acid; benzene; 2.1: Mitsunobu reaction;

DOI:10.1135/cccc20051429

Reference yield:

1,6-anhydro-3-(3-hydroxypropyl)-2,4-di-O-tosyl-β-D-allopyranose (916676-56-7) → 3-C-(3-aminopropyl)-1,6-anhydro-2,4-di-O-tosyl-β-D-allopyranose (916676-59-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 95 percent / Ph₃P; diisopropyl diazenedicarboxylate; HN₃ / tetrahydrofuran; benzene / 1 h / 20 °C

2: 73 percent / H₂ / Pd/C / CHCl₃; methanol; acetic acid / 48 h / 20 °C

With tris-(2-chloro-ethyl)-amine; di-isopropyl azodicarboxylate; hydrogen; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; methanol; chloroform; acetic acid; benzene; 1: Mitsunobu reaction;

DOI:10.1135/cccc20051429

upstream raw materials:

1,6-anhydro-3-C-(3-azidopropyl)-2,4-di-O-tosyl-β-D-allopyranose

3-C-allyl-1,6-anhydro-2,4-di-O-tosyl-β-D-allopyranose

1,6-anhydro-3-(3-hydroxypropyl)-2,4-di-O-tosyl-β-D-allopyranose

1,6-anhydro-2,4-di-O-p-tolylsulfonyl-β-D-ribo-hexopyranos-3-ulose

Downstream raw materials:

1,6-anhydro-2,4-di-O-tosyl-3-C-[3-(tosylamino)propyl]-β-D-allopyranose