methyl-5-O-benzyl-2,3,6-tridesoxy-α-D-erythro-hex-2-enofuranoside

Base Information

• Chemical Name: methyl-5-O-benzyl-2,3,6-tridesoxy-α-D-erythro-hex-2-enofuranoside
• CAS No.: 74652-75-8
• Molecular Formula: C₁₄H₁₈O₃
• Molecular Weight: 234.295
• Mol file: 74652-75-8.mol

Synonyms:

Chemical Property of methyl-5-O-benzyl-2,3,6-tridesoxy-α-D-erythro-hex-2-enofuranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl-5-O-benzyl-2,3,6-tridesoxy-α-D-erythro-hex-2-enofuranoside

There total 5 articles about methyl-5-O-benzyl-2,3,6-tridesoxy-α-D-erythro-hex-2-enofuranoside 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:

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-5-O-benzyl-2,3,6-tridesoxy-α-D-erythro-hex-2-enofuranoside (74652-75-8)

Guidance literature:

Multi-step reaction with 3 steps

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

2: 90 percent / pyridine / Ambient temperature

3: sodium azide / hexamethylphosphoric acid triamide / 60 h / 80 °C

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

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

Reference yield:

methyl 3,6-dideoxy-α-D-arabino-hexopyranoside (6154-71-8) → methyl-5-O-benzyl-2,3,6-tridesoxy-α-D-erythro-hex-2-enofuranoside (74652-75-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 95 percent / aluminium chloride / dioxane / 0.5 h / Ambient temperature

2: 95 percent / 4 percent potassium hydroxyde / methanol / Ambient temperature

3: 90 percent / pyridine / Ambient temperature

4: sodium azide / hexamethylphosphoric acid triamide / 60 h / 80 °C

With potassium hydroxide; aluminium trichloride; sodium azide; In 1,4-dioxane; pyridine; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide;

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