methyl 3-azido-5-O-benzyl-2,3,6-trideoxy-α-L-lyxo-hexofuranoside

Base Information

• Chemical Name: methyl 3-azido-5-O-benzyl-2,3,6-trideoxy-α-L-lyxo-hexofuranoside
• CAS No.: 78841-78-8
• Molecular Formula: C₁₄H₁₉N₃O₃
• Molecular Weight: 277.323
• Mol file: 78841-78-8.mol

Synonyms:methyl 3-azido-5-O-benzyl-2,3,6-trideoxy-α-L-lyxo-hexofuranoside

Chemical Property of methyl 3-azido-5-O-benzyl-2,3,6-trideoxy-α-L-lyxo-hexofuranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 3-azido-5-O-benzyl-2,3,6-trideoxy-α-L-lyxo-hexofuranoside

There total 22 articles about methyl 3-azido-5-O-benzyl-2,3,6-trideoxy-α-L-lyxo-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: 93.0%

methyl 5-O-benzyl-2,6-dideoxy-3-O-(methylsulfonyl)-α-L-lyxo-hexofuranoside (78841-77-7) → methyl 3-azido-5-O-benzyl-2,3,6-trideoxy-α-L-lyxo-hexofuranoside (78841-78-8)

Guidance literature:

With sodium azide; In N,N-dimethyl-formamide; at 120 ℃; for 0.5h;

DOI:10.1016/S0008-6215(00)80395-X

Reference yield:

6-deoxy-1,2-O-isopropylidene-3-O-(methylsulfonyl)-β-L-idofuranose (64243-86-3) → methyl 3-azido-5-O-benzyl-2,3,6-trideoxy-α-L-lyxo-hexofuranoside (78841-78-8)

Guidance literature:

Multi-step reaction with 9 steps

1: 53 percent / KOH / dimethylformamide / 1 h / 25 - 28 °C

2: 94 percent / LiAlH₄ / diethyl ether / 1.) 6 h, reflux; 2.) RT, overnight

3: 92 percent / pyridine / 3 h / Ambient temperature

4: 48.5 percent / 0.35 M methanolic HCl / 16 h / Ambient temperature

5: 56.5 percent / pyridine / 1.) 24 h, RT; 2.) 6 h, steam bath

6: 97 percent / 4.65 M methanolic NaOMe / CHCl₃ / 0.5 h

7: 98 percent / LiAlH₄ / diethyl ether / 0.5 h / -10 °C

8: 77.5 percent / pyridine / 4 h / Ambient temperature

9: 93 percent / NaN₃ / dimethylformamide / 0.5 h / 120 °C

With hydrogenchloride; potassium hydroxide; lithium aluminium tetrahydride; sodium azide; sodium methylate; In pyridine; diethyl ether; chloroform; N,N-dimethyl-formamide;

DOI:10.1016/S0008-6215(00)80395-X

Reference yield:

5,6-Anhydro-1,2-O-isopropylidene-3-O-(methylsulfonyl)-β-L-idofuranose (19286-05-6) → methyl 3-azido-5-O-benzyl-2,3,6-trideoxy-α-L-lyxo-hexofuranoside (78841-78-8)

Guidance literature:

Multi-step reaction with 10 steps

1: 94 percent / LiAlH₄ / tetrahydrofuran / 0.75 h / -5 °C

2: 53 percent / KOH / dimethylformamide / 1 h / 25 - 28 °C

3: 94 percent / LiAlH₄ / diethyl ether / 1.) 6 h, reflux; 2.) RT, overnight

4: 92 percent / pyridine / 3 h / Ambient temperature

5: 48.5 percent / 0.35 M methanolic HCl / 16 h / Ambient temperature

6: 56.5 percent / pyridine / 1.) 24 h, RT; 2.) 6 h, steam bath

7: 97 percent / 4.65 M methanolic NaOMe / CHCl₃ / 0.5 h

8: 98 percent / LiAlH₄ / diethyl ether / 0.5 h / -10 °C

9: 77.5 percent / pyridine / 4 h / Ambient temperature

10: 93 percent / NaN₃ / dimethylformamide / 0.5 h / 120 °C

With hydrogenchloride; potassium hydroxide; lithium aluminium tetrahydride; sodium azide; sodium methylate; In tetrahydrofuran; pyridine; diethyl ether; chloroform; N,N-dimethyl-formamide;

DOI:10.1016/S0008-6215(00)80395-X

upstream raw materials:

methyl 5-O-benzyl-2,6-dideoxy-3-O-(methylsulfonyl)-α-L-lyxo-hexofuranoside

6-deoxy-1,2-O-isopropylidene-3-O-(methylsulfonyl)-β-L-idofuranose

5,6-Anhydro-1,2-O-isopropylidene-3-O-(methylsulfonyl)-β-L-idofuranose

6-O-benzoyl-1,2-O-isopropylidene-α-D-glucofuranose

Downstream raw materials:

methyl 3-acetamido-5-O-benzyl-2,3,6-trideoxy-α-L-lyxo-hexofuranoside

methyl 2,3,6-trideoxy-5-O-(p-nitrobenzoyl)-3-(trifluoroacetamido)-α-L-lyxo-hexofuranoside

methyl 3-amino-5-O-benzyl-2,3,6-trideoxy-α-L-lyxo-hexofuranoside