(R)-2-(((1R,2S,3R,4R,5R)-4-azido-2-(benzyloxy)-6,8-dioxabicyclo[3.2.1]octan-3-yl)oxy)propanoic acid

Base Information

• Chemical Name: (R)-2-(((1R,2S,3R,4R,5R)-4-azido-2-(benzyloxy)-6,8-dioxabicyclo[3.2.1]octan-3-yl)oxy)propanoic acid
• CAS No.: 104430-61-7
• Molecular Formula: C₁₆H₁₉N₃O₆
• Molecular Weight: 349.343
• Mol file: 104430-61-7.mol

Synonyms:(R)-2-(((1R,2S,3R,4R,5R)-4-azido-2-(benzyloxy)-6,8-dioxabicyclo[3.2.1]octan-3-yl)oxy)propanoic acid

Chemical Property of (R)-2-(((1R,2S,3R,4R,5R)-4-azido-2-(benzyloxy)-6,8-dioxabicyclo[3.2.1]octan-3-yl)oxy)propanoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-2-(((1R,2S,3R,4R,5R)-4-azido-2-(benzyloxy)-6,8-dioxabicyclo[3.2.1]octan-3-yl)oxy)propanoic acid

There total 5 articles about (R)-2-(((1R,2S,3R,4R,5R)-4-azido-2-(benzyloxy)-6,8-dioxabicyclo[3.2.1]octan-3-yl)oxy)propanoic acid 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: 100.0%

1,6-Anhydro-2-azido-4-O-benzyl-2-desoxy-3-O-<(1R)-1-(methoxycarbonyl)ethyl>-β-D-glucopyranose (104430-62-8) → (R)-2-(((1R,2S,3R,4R,5R)-4-azido-2-(benzyloxy)-6,8-dioxabicyclo[3.2.1]octan-3-yl)oxy)propanoic acid (104430-61-7)

Guidance literature:

With lithium hydroxide; In 1,4-dioxane; methanol; water; at 20 ℃; pH=9.5 - 10;

DOI:10.1002/1099-0690(200208)2002:16<2710::AID-EJOC2710>3.0.CO;2-8

Reference yield: 74.0%

(S)-2-chloropropanoic acid (29617-66-1) + 1,6-anhydro-2-azido-4-O-benzyl-2-deoxy-β-D-glucopyranose (55682-47-8) → (R)-2-(((1R,2S,3R,4R,5R)-4-azido-2-(benzyloxy)-6,8-dioxabicyclo[3.2.1]octan-3-yl)oxy)propanoic acid (104430-61-7)

Guidance literature:

1,6-anhydro-2-azido-4-O-benzyl-2-deoxy-β-D-glucopyranose; With sodium hydride; In 1,4-dioxane; mineral oil; at 45 ℃; for 0.166667h;

(S)-2-chloropropanoic acid; In 1,4-dioxane; mineral oil; at 90 ℃; for 2h;

Reference yield:

1,6-anhydro-2-azido-4-O-benzyl-2-deoxy-β-D-glucopyranose (55682-47-8) → (R)-2-(((1R,2S,3R,4R,5R)-4-azido-2-(benzyloxy)-6,8-dioxabicyclo[3.2.1]octan-3-yl)oxy)propanoic acid (104430-61-7)

Guidance literature:

Multi-step reaction with 2 steps

1: NaH / CH₂Cl₂

2: 100 percent / LiOH / dioxane; H₂O; methanol / 20 °C / pH 9.5 - 10

With lithium hydroxide; sodium hydride; In 1,4-dioxane; methanol; dichloromethane; water;

DOI:10.1002/1099-0690(200208)2002:16<2710::AID-EJOC2710>3.0.CO;2-8

upstream raw materials:

(S)-2-chloropropanoic acid

1,6-anhydro-2-azido-4-O-benzyl-2-deoxy-β-D-glucopyranose

1,6-Anhydro-2-azido-4-O-benzyl-2-desoxy-3-O-<(1R)-1-(methoxycarbonyl)ethyl>-β-D-glucopyranose

4-O-benzyl-D-(-)-glucal

Downstream raw materials:

1,6-Anhydro-2-azido-4-O-benzyl-2-desoxy-3-O-<(1R)-1-(methoxycarbonyl)ethyl>-β-D-glucopyranose

1,6-anhydro-2-azido-4-O-benzyl-2-deoxy-3-O-{(2R)-propionyl-[L-alanyl-(D-isoglutamyl α-methyl ester)-(7-methyl)-1-(2-trimethylsilylethyl) (2S,6S)-N^ε-(tert-butyloxycarbonyl)-2,6-diaminopimelate]-2-yl}-β-D-glucopyranose

1,6-anhydro-2-azido-4-O-benzyl-2-deoxy-3-O-{(2R)-propionyl-[L-alanyl-(D-isoglutamyl α-methyl ester)-(7-methyl)-1-(2-trimethylsilylethyl) (2S,6R)-N^ε-(tert-butyloxycarbonyl)-2,6-diaminopimelate]-2-yl}-β-D-glucopyranose

2-Acetamido-1,6-anhydro-4-O-benzyl-3,O-<(1R)-1-carboxyethyl>-2-desoxy-β-D-glucopyranose