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

Base Information

• Chemical Name: 1,6-Anhydro-2-azido-4-O-benzyl-2-desoxy-3-O-<(1R)-1-(methoxycarbonyl)ethyl>-β-D-glucopyranose
• CAS No.: 104430-62-8
• Molecular Formula: C₁₇H₂₁N₃O₆
• Molecular Weight: 363.37
• Mol file: 104430-62-8.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 10 articles about 1,6-Anhydro-2-azido-4-O-benzyl-2-desoxy-3-O-<(1R)-1-(methoxycarbonyl)ethyl>-β-D-glucopyranose 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 (2R)-2-chloropropanoate (77287-29-7) + 1,6-anhydro-2-azido-4-O-benzyl-2-deoxy-β-D-glucopyranose (55682-47-8) → 1,6-Anhydro-2-azido-4-O-benzyl-2-desoxy-3-O-<(1R)-1-(methoxycarbonyl)ethyl>-β-D-glucopyranose (104430-62-8) + 1,6-Anhydro-2-azido-4-O-benzyl-2-desoxy-3-O-<(1S)-1-(methoxycarbonyl)ethyl>-β-D-glucopyranose

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 105 ℃; for 16h;

DOI:10.1016/j.tet.2013.06.079

Reference yield:

4-O-benzyl-D-(-)-glucal (58871-11-7) → 1,6-Anhydro-2-azido-4-O-benzyl-2-desoxy-3-O-<(1R)-1-(methoxycarbonyl)ethyl>-β-D-glucopyranose (104430-62-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: (Bu₃Sn)2O; mol. sieves 3 Angstroem / acetonitrile / 3 h / Heating

1.2: 89 percent / I₂ / acetonitrile / 0.75 h / 20 °C

2.1: 79 percent / tetramethyl guanidinium azide / dimethylformamide / 72 h / 120 °C

3.1: NaH / CH₂Cl₂

With N,N,N',N'-tetramethylguanidinium azide; 3 A molecular sieve; sodium hydride; bis(tri-n-butyltin)oxide; In dichloromethane; N,N-dimethyl-formamide; acetonitrile;

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

Reference yield:

1,6-anhydro-4-O-benzyl-2-iodo-2-deoxy-β-D-glucopyranose (50767-55-0) → 1,6-Anhydro-2-azido-4-O-benzyl-2-desoxy-3-O-<(1R)-1-(methoxycarbonyl)ethyl>-β-D-glucopyranose (104430-62-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 79 percent / tetramethyl guanidinium azide / dimethylformamide / 72 h / 120 °C

2: NaH / CH₂Cl₂

With N,N,N',N'-tetramethylguanidinium azide; sodium hydride; In dichloromethane; N,N-dimethyl-formamide;

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

upstream raw materials:

diazomethane

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

methyl (S)-2-[(trifluoromethanesulfonyl)oxy]propionate

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

Downstream raw materials:

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

2-Acetamido-1,6-anhydro-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