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

Base Information

• Chemical Name: 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
• CAS No.: 478920-33-1
• Molecular Formula: C₄₃H₆₇N₇O₁₅Si
• Molecular Weight: 950.128

Synonyms:

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Useful:

Technology Process of 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

There total 20 articles about 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 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:

2-(Trimethylsilyl)ethanol (2916-68-9) → 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)-Nε-(tert-butyloxycarbonyl)-2,6-diaminopimelate]-2-yl}-β-D-glucopyranose (478920-33-1)

Guidance literature:

Multi-step reaction with 7 steps

1: LiHMDS / tetrahydrofuran / 0 °C

2: H₂ / 10percent Pd/C / methanol

3: PyBOP; NMM / CH₂Cl₂ / 20 °C / pH 9 - 9.5

4: H₂ / 10percent Pd/C / methanol

5: PyBOP; NMM / CH₂Cl₂ / 20 °C / pH 9 - 9.5

6: H₂ / 10percent Pd/C / methanol

7: PyBOP; NMM / dimethylformamide / 20 °C / pH 9 - 9.5

With 4-methyl-morpholine; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; hydrogen; lithium hexamethyldisilazane; 10percent Pd/C; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;

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

Reference yield:

(S)-3-(3-benzyloxycarbonyl-5-oxo-1,3-oxazolidin-4-yl)propionaldehyde (89969-26-6) → 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)-Nε-(tert-butyloxycarbonyl)-2,6-diaminopimelate]-2-yl}-β-D-glucopyranose (478920-33-1)

Guidance literature:

Multi-step reaction with 10 steps

1.1: KHMDS / tetrahydrofuran / 0.25 h / -78 - -55 °C

1.2: 76 percent / tetrahydrofuran / -78 - -30 °C

2.1: 65 percent / LiHMDS / tetrahydrofuran / 0 °C

3.1: H₂ / Pd(OH)2/C / methanol

4.1: NaHCO₃ / tetrahydrofuran; H₂O / 1 h

5.1: H₂ / 10percent Pd/C / methanol

6.1: PyBOP; NMM / CH₂Cl₂ / 20 °C / pH 9 - 9.5

7.1: H₂ / 10percent Pd/C / methanol

8.1: PyBOP; NMM / CH₂Cl₂ / 20 °C / pH 9 - 9.5

9.1: H₂ / 10percent Pd/C / methanol

10.1: PyBOP; NMM / dimethylformamide / 20 °C / pH 9 - 9.5

With 4-methyl-morpholine; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; hydrogen; potassium hexamethylsilazane; sodium hydrogencarbonate; lithium hexamethyldisilazane; palladium dihydroxide; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; 1.2: Wittig-Horner reaction;

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

Reference yield:

(S)-4-<2'-(Chloroformyl)ethyl>-5-oxooxazolidin-3-carbonsaeure-benzylester (58456-26-1) → 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)-Nε-(tert-butyloxycarbonyl)-2,6-diaminopimelate]-2-yl}-β-D-glucopyranose (478920-33-1)

Guidance literature:

Multi-step reaction with 11 steps

1.1: 73 percent / LiAl(OtBu)3H / tetrahydrofuran / -78 °C

2.1: KHMDS / tetrahydrofuran / 0.25 h / -78 - -55 °C

2.2: 76 percent / tetrahydrofuran / -78 - -30 °C

3.1: 65 percent / LiHMDS / tetrahydrofuran / 0 °C

4.1: H₂ / Pd(OH)2/C / methanol

5.1: NaHCO₃ / tetrahydrofuran; H₂O / 1 h

6.1: H₂ / 10percent Pd/C / methanol

7.1: PyBOP; NMM / CH₂Cl₂ / 20 °C / pH 9 - 9.5

8.1: H₂ / 10percent Pd/C / methanol

9.1: PyBOP; NMM / CH₂Cl₂ / 20 °C / pH 9 - 9.5

10.1: H₂ / 10percent Pd/C / methanol

11.1: PyBOP; NMM / dimethylformamide / 20 °C / pH 9 - 9.5

With 4-methyl-morpholine; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; hydrogen; potassium hexamethylsilazane; sodium hydrogencarbonate; lithium tri-t-butoxyaluminum hydride; lithium hexamethyldisilazane; palladium dihydroxide; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; 2.2: Wittig-Horner reaction;

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

upstream 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-(Trimethylsilyl)ethanol

(S)-3-(3-benzyloxycarbonyl-5-oxo-1,3-oxazolidin-4-yl)propionaldehyde

(S)-4-<2'-(Chloroformyl)ethyl>-5-oxooxazolidin-3-carbonsaeure-benzylester

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