methyl-2-azido-5-O-benzyl-2,3,6-tridesoxy-α-D-ribo-hexofuranoside

Base Information

• Chemical Name: methyl-2-azido-5-O-benzyl-2,3,6-tridesoxy-α-D-ribo-hexofuranoside
• CAS No.: 74652-74-7
• Molecular Formula: C₁₄H₁₉N₃O₃
• Molecular Weight: 277.323
• Mol file: 74652-74-7.mol

Synonyms:methyl-2-azido-5-O-benzyl-2,3,6-tridesoxy-α-D-ribo-hexofuranoside

Chemical Property of methyl-2-azido-5-O-benzyl-2,3,6-tridesoxy-α-D-ribo-hexofuranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl-2-azido-5-O-benzyl-2,3,6-tridesoxy-α-D-ribo-hexofuranoside

There total 6 articles about methyl-2-azido-5-O-benzyl-2,3,6-tridesoxy-α-D-ribo-hexofuranoside 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: 65.0%

Trifluoro-methanesulfonic acid (2S,3S,5S)-5-((R)-1-benzyloxy-ethyl)-2-methoxy-tetrahydro-furan-3-yl ester → methyl-2-azido-5-O-benzyl-2,3,6-tridesoxy-α-D-ribo-hexofuranoside (74652-74-7)

Guidance literature:

With sodium azide; In N,N,N,N,N,N-hexamethylphosphoric triamide; for 2h; Ambient temperature;

DOI:10.1016/S0008-6215(00)85654-2

Reference yield:

methyl-5-O-benzyl-3,6-didesoxy-2-O-tosyl-α-D-arabino-hexofuranoside (74652-73-6) → methyl-5-O-benzyl-2,3,6-tridesoxy-α-D-erythro-hex-2-enofuranoside (74652-75-8) + methyl-2-azido-5-O-benzyl-2,3,6-tridesoxy-α-D-ribo-hexofuranoside (74652-74-7)

Guidance literature:

With sodium azide; In N,N-dimethyl-formamide; at 145 ℃; for 16h; Yield given. Yields of byproduct given;

DOI:10.1016/S0008-6215(00)85654-2

Reference yield:

methyl 2-O-benzoyl-5-O-benzyl-3,6-dideoxy-α-D-arabino-hexofuranoside (63225-18-3) → methyl-2-azido-5-O-benzyl-2,3,6-tridesoxy-α-D-ribo-hexofuranoside (74652-74-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 95 percent / 4 percent potassium hydroxyde / methanol / Ambient temperature

2: 94 percent / pyridine / CH₂Cl₂ / 2 h / -15 °C

3: 65 percent / sodium azide / hexamethylphosphoric acid triamide / 2 h / Ambient temperature

With pyridine; potassium hydroxide; sodium azide; In methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane;

DOI:10.1016/S0008-6215(00)85654-2

upstream raw materials:

methyl-5-O-benzyl-3,6-didesoxy-2-O-tosyl-α-D-arabino-hexofuranoside

methyl 2-O-benzoyl-5-O-benzyl-3,6-dideoxy-α-D-arabino-hexofuranoside

methyl 3,6-dideoxy-α-D-arabino-hexopyranoside

benzaldehyde