1,4-anhydro-2-deoxy-2-acetamido-3,5-di-O-benzyl-4-thio-D-arabinitol

Base Information

• Chemical Name: 1,4-anhydro-2-deoxy-2-acetamido-3,5-di-O-benzyl-4-thio-D-arabinitol
• CAS No.: 898806-15-0
• Molecular Formula: C₂₁H₂₅NO₃S
• Molecular Weight: 371.5
• Mol file: 898806-15-0.mol

Synonyms:1,4-anhydro-2-deoxy-2-acetamido-3,5-di-O-benzyl-4-thio-D-arabinitol

Chemical Property of 1,4-anhydro-2-deoxy-2-acetamido-3,5-di-O-benzyl-4-thio-D-arabinitol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1,4-anhydro-2-deoxy-2-acetamido-3,5-di-O-benzyl-4-thio-D-arabinitol

There total 7 articles about 1,4-anhydro-2-deoxy-2-acetamido-3,5-di-O-benzyl-4-thio-D-arabinitol 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:

N-((3S,4S,5R)-4-Hydroxy-5-hydroxymethyl-tetrahydro-thiophen-3-yl)-acetamide + benzyl bromide (100-39-0) → 1,4-anhydro-2-deoxy-2-acetamido-3,5-di-O-benzyl-4-thio-D-arabinitol (898806-15-0)

Guidance literature:

With barium hydroxide octahydrate; barium(II) oxide; In N,N-dimethyl-formamide; at 20 ℃; for 12h;

DOI:10.1021/jo060167w

Reference yield:

1,4-anhydro-2-deoxy-2-amino-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-4-thio-D-arabinitol (898806-13-8) → 1,4-anhydro-2-deoxy-2-acetamido-3,5-di-O-benzyl-4-thio-D-arabinitol (898806-15-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 77 percent / pyridine / 7 h / 20 °C

2: tetra-n-butylammonium fluoride / tetrahydrofuran / 1 h / 0 °C

3: 100 mg / barium oxide; barium hydroxide octahydrate / dimethylformamide / 12 h / 20 °C

With barium hydroxide octahydrate; tetrabutyl ammonium fluoride; barium(II) oxide; In tetrahydrofuran; pyridine; N,N-dimethyl-formamide;

DOI:10.1021/jo060167w

Reference yield:

1,4-anhydro-2-deoxy-2-azido-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-4-thio-D-arabinitol (898806-11-6) → 1,4-anhydro-2-deoxy-2-acetamido-3,5-di-O-benzyl-4-thio-D-arabinitol (898806-15-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 70 percent / triphenylphosphine / dioxane; methanol; H₂O / 14 h / 55 °C

2: 77 percent / pyridine / 7 h / 20 °C

3: tetra-n-butylammonium fluoride / tetrahydrofuran / 1 h / 0 °C

4: 100 mg / barium oxide; barium hydroxide octahydrate / dimethylformamide / 12 h / 20 °C

With barium hydroxide octahydrate; tetrabutyl ammonium fluoride; triphenylphosphine; barium(II) oxide; In tetrahydrofuran; 1,4-dioxane; pyridine; methanol; water; N,N-dimethyl-formamide;

DOI:10.1021/jo060167w

upstream raw materials:

benzyl bromide

1,4-anhydro-2-deoxy-2-amino-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-4-thio-D-arabinitol

1,4-anhydro-2-deoxy-2-azido-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-4-thio-D-arabinitol

1,4-anhydro-2-deoxy-2-acetamido-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-4-thio-D-arabinitol