methyl (6'-azido-3'-O-benzyl-6'-deoxy-2',4'-di-O-methoxymethyl-α-D-glucopyranosyl)ethanoate

Base Information

• Chemical Name: methyl (6'-azido-3'-O-benzyl-6'-deoxy-2',4'-di-O-methoxymethyl-α-D-glucopyranosyl)ethanoate
• CAS No.: 854377-22-3
• Molecular Formula: C₂₀H₂₉N₃O₈
• Molecular Weight: 439.466
• Mol file: 854377-22-3.mol

Synonyms:methyl (6'-azido-3'-O-benzyl-6'-deoxy-2',4'-di-O-methoxymethyl-α-D-glucopyranosyl)ethanoate

Chemical Property of methyl (6'-azido-3'-O-benzyl-6'-deoxy-2',4'-di-O-methoxymethyl-α-D-glucopyranosyl)ethanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (6'-azido-3'-O-benzyl-6'-deoxy-2',4'-di-O-methoxymethyl-α-D-glucopyranosyl)ethanoate

There total 1 articles about methyl (6'-azido-3'-O-benzyl-6'-deoxy-2',4'-di-O-methoxymethyl-α-D-glucopyranosyl)ethanoate 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:

(6'-azido-3'-O-benzyl-6'-deoxy-2',4'-di-O-methoxymethyl-α-D-glucopyranosyl)ethanoic acid (854377-20-1) + methyl iodide (74-88-4) → methyl (6'-azido-3'-O-benzyl-6'-deoxy-2',4'-di-O-methoxymethyl-α-D-glucopyranosyl)ethanoate (854377-22-3)

Guidance literature:

With sodium hydrogencarbonate; In N,N-dimethyl-formamide; for 72h;

DOI:10.1021/jo0502899

Reference yield: 98.5%

methyl (6'-azido-3'-O-benzyl-6'-deoxy-2',4'-di-O-methoxymethyl-α-D-glucopyranosyl)ethanoate (854377-22-3) → methyl (6'-amino-3'-O-benzyl-6'-deoxy-2',4'-di-O-methoxymethyl-α-D-glucopyranosyl)ethanoate (854377-24-5)

Guidance literature:

With triphenylphosphine; In tetrahydrofuran; water; at 20 ℃; for 48h;

DOI:10.1021/jo0502899

Reference yield:

methyl (6'-azido-3'-O-benzyl-6'-deoxy-2',4'-di-O-methoxymethyl-α-D-glucopyranosyl)ethanoate (854377-22-3) → (1R,6R,7S,8R,9R,10R,15R,16S,17R,18R)-8,17-Bis-benzyloxy-7,9,16,18-tetrahydroxy-19,20-dioxa-3,12-diaza-tricyclo[13.3.1.16,10]icosane-4,13-dione (854377-28-9)

Guidance literature:

Multi-step reaction with 6 steps

1: 98.5 percent / triphenylphosphine / tetrahydrofuran; H₂O / 48 h / 20 °C

2: 83 percent / diethyl phosphoryl cyanide; Et₃N / dimethylformamide / 20 °C

3: 93 percent / LiOH / tetrahydrofuran; methanol; H₂O / 20 °C

4: H₂ / Pd/C / methanol

5: 400 mg / diethyl phosphoryl cyanide; Et₃N / dimethylformamide / 20 °C

6: 98 percent / HCl / methanol / 50 °C

With hydrogenchloride; lithium hydroxide; diethyl cyanophosphonate; hydrogen; triethylamine; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; methanol; water; N,N-dimethyl-formamide;

DOI:10.1021/jo0502899

upstream raw materials:

(6'-azido-3'-O-benzyl-6'-deoxy-2',4'-di-O-methoxymethyl-α-D-glucopyranosyl)ethanoic acid

methyl iodide

Downstream raw materials:

methyl (6'-amino-3'-O-benzyl-6'-deoxy-2',4'-di-O-methoxymethyl-α-D-glucopyranosyl)ethanoate

(1R,6R,7S,8R,9R,10R,15R,16S,17R,18R)-8,17-Bis-benzyloxy-7,9,16,18-tetrahydroxy-19,20-dioxa-3,12-diaza-tricyclo[13.3.1.1^6,10]icosane-4,13-dione

(1R,6R,7S,8R,9R,10R,15R,16S,17R,18R)-8,17-Bis-benzyloxy-7,9,16,18-tetrakis-methoxymethoxy-19,20-dioxa-3,12-diaza-tricyclo[13.3.1.1^6,10]icosane

(1R,6R,7S,8R,9R,10R,15R,16S,17R,18R)-8,17-Bis-benzyloxy-7,9,16,18-tetrakis-methoxymethoxy-19,20-dioxa-3,12-diaza-tricyclo[13.3.1.1^6,10]icosane-4,13-dione