2-Azido-3-O-benzyl-1,2,5-trideoxy-1,5-imino-D-galactitol

Base Information

• Chemical Name: 2-Azido-3-O-benzyl-1,2,5-trideoxy-1,5-imino-D-galactitol
• CAS No.: 121624-33-7
• Molecular Formula: C₁₃H₁₈N₄O₃
• Molecular Weight: 278.311
• Mol file: 121624-33-7.mol

Synonyms:2-Azido-3-O-benzyl-1,2,5-trideoxy-1,5-imino-D-galactitol

Chemical Property of 2-Azido-3-O-benzyl-1,2,5-trideoxy-1,5-imino-D-galactitol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-Azido-3-O-benzyl-1,2,5-trideoxy-1,5-imino-D-galactitol

There total 12 articles about 2-Azido-3-O-benzyl-1,2,5-trideoxy-1,5-imino-D-galactitol 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: 79.0%

2-Azido-3-O-benzyl-N,6-O-carbonyl-1,2,5-trideoxy-1,5-imino-D-galactitol (121701-83-5) → 2-Azido-3-O-benzyl-1,2,5-trideoxy-1,5-imino-D-galactitol (121624-33-7)

Guidance literature:

With barium dihydroxide; In methanol; water; for 8h; Heating;

DOI:10.1016/0008-6215(90)80030-7

Reference yield:

N-benzyl-1,5-dideoxy-1,5-imino-4,6-O-isopropylidene-D-mannitol (114129-23-6) → 2-Azido-3-O-benzyl-1,2,5-trideoxy-1,5-imino-D-galactitol (121624-33-7)

Guidance literature:

Multi-step reaction with 11 steps

1: 99 percent / H₂, glacial acetic acid / 10percent Pd-C / methanol / 5 h / 40 °C / 2250.2 Torr

2: 87 percent / K₂CO₃ / dimethylformamide / 0.5 h / 0 °C

3: 99 percent / SOCl₂, NEt₃ / ethyl acetate / 1 h / 0 °C

4: 52 percent / LiN₃ / dimethylformamide / 8 h / 90 °C

5: 81 percent / KOH / tetrahydrofuran / 8 h / 60 °C

6: 98 percent / conc.HCl / aq. acetic acid; CH₂Cl₂ / 1.5 h / 60 °C / pH 3

7: 82 percent / K₂CO₃ / dimethylformamide; H₂O / 8 h / 60 °C

8: 81 percent / NEt₃ / acetone / 0.5 h / 0 °C

9: 94 percent / dimethylformamide / 72 h / 100 °C

10: 94 percent / 10 M NaOH / methanol; CH₂Cl₂ / 8 h / 40 °C

11: 79 percent / Ba(OH)2*8H₂O / methanol; H₂O / 8 h / Heating

With hydrogenchloride; barium dihydroxide; potassium hydroxide; sodium hydroxide; thionyl chloride; lithium azide; hydrogen; potassium carbonate; acetic acid; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water; acetic acid; ethyl acetate; N,N-dimethyl-formamide; acetone;

DOI:10.1016/0008-6215(90)80030-7

Reference yield:

benzyl bromide (100-39-0) → 2-Azido-3-O-benzyl-1,2,5-trideoxy-1,5-imino-D-galactitol (121624-33-7)

Guidance literature:

Multi-step reaction with 7 steps

1: 81 percent / KOH / tetrahydrofuran / 8 h / 60 °C

2: 98 percent / conc.HCl / aq. acetic acid; CH₂Cl₂ / 1.5 h / 60 °C / pH 3

3: 82 percent / K₂CO₃ / dimethylformamide; H₂O / 8 h / 60 °C

4: 81 percent / NEt₃ / acetone / 0.5 h / 0 °C

5: 94 percent / dimethylformamide / 72 h / 100 °C

6: 94 percent / 10 M NaOH / methanol; CH₂Cl₂ / 8 h / 40 °C

7: 79 percent / Ba(OH)2*8H₂O / methanol; H₂O / 8 h / Heating

With hydrogenchloride; barium dihydroxide; potassium hydroxide; sodium hydroxide; potassium carbonate; triethylamine; In tetrahydrofuran; methanol; dichloromethane; water; acetic acid; N,N-dimethyl-formamide; acetone;

DOI:10.1016/0008-6215(90)80030-7

upstream raw materials:

2-Azido-3-O-benzyl-N,6-O-carbonyl-1,2,5-trideoxy-1,5-imino-D-galactitol

benzyl bromide

N-benzyl-1,5-dideoxy-1,5-imino-4,6-O-isopropylidene-D-mannitol

(3aR,5aR,9aR,9bS)-8,8-Dimethyl-2-oxo-hexahydro-1,3,7,9-tetraoxa-2λ⁴-thia-5-aza-cyclopenta[a]naphthalene-5-carboxylic acid benzyl ester

Downstream raw materials:

N-((3S,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)piperidin-3-yl)acetamide