methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-2,6-anhydro-3,5-dideoxy-2-C-{1-[3S-(benzyloxycarbonyl)amino-4-(tetrahydro-2H-pyran-2-yloxy)-1-butanol]}-D-erythro-L-manno-nonanoate

Base Information

Chemical Name:methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-2,6-anhydro-3,5-dideoxy-2-C-{1-[3S-(benzyloxycarbonyl)amino-4-(tetrahydro-2H-pyran-2-yloxy)-1-butanol]}-D-erythro-L-manno-nonanoate
CAS No.:511546-71-7
Molecular Formula:C₃₇H₅₂N₂O₁₇
Molecular Weight:796.823
Hs Code.:

methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-2,6-anhydro-3,5-dideoxy-2-C-{1-[3S-(benzyloxycarbonyl)amino-4-(tetrahydro-2H-pyran-2-yloxy)-1-butanol]}-D-erythro-L-manno-nonanoate

Synonyms:methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-2,6-anhydro-3,5-dideoxy-2-C-{1-[3S-(benzyloxycarbonyl)amino-4-(tetrahydro-2H-pyran-2-yloxy)-1-butanol]}-D-erythro-L-manno-nonanoate

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Chemical Property of methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-2,6-anhydro-3,5-dideoxy-2-C-{1-[3S-(benzyloxycarbonyl)amino-4-(tetrahydro-2H-pyran-2-yloxy)-1-butanol]}-D-erythro-L-manno-nonanoate

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Technology Process of methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-2,6-anhydro-3,5-dideoxy-2-C-{1-[3S-(benzyloxycarbonyl)amino-4-(tetrahydro-2H-pyran-2-yloxy)-1-butanol]}-D-erythro-L-manno-nonanoate

There total 8 articles about methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-2,6-anhydro-3,5-dideoxy-2-C-{1-[3S-(benzyloxycarbonyl)amino-4-(tetrahydro-2H-pyran-2-yloxy)-1-butanol]}-D-erythro-L-manno-nonanoate 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: 45.0%

: 121512-93-4
[methyl (5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosyl)onate] phenyl sulfone

: 511546-70-6
[(S)-3-Oxo-1-(tetrahydro-pyran-2-yloxymethyl)-propyl]-carbamic acid benzyl ester

: 511546-71-7
methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-2,6-anhydro-3,5-dideoxy-2-C-{1-[3S-(benzyloxycarbonyl)amino-4-(tetrahydro-2H-pyran-2-yloxy)-1-butanol]}-D-erythro-L-manno-nonanoate

Guidance literature:: With samarium diiodide; In tetrahydrofuran; at 20 ℃; for 8h;
DOI:10.1021/jo026776v

Reference yield:

: 501-53-1,94274-21-2
benzyl chloroformate

: 511546-71-7
methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-2,6-anhydro-3,5-dideoxy-2-C-{1-[3S-(benzyloxycarbonyl)amino-4-(tetrahydro-2H-pyran-2-yloxy)-1-butanol]}-D-erythro-L-manno-nonanoate

Guidance literature:: Multi-step reaction with 8 steps

1.1: 89 percent / aq. NaHCO₃ / 24 h / 20 °C

2.1: NaOH / H₂O; ethanol / 24 h / 20 °C

2.2: 96 percent / dimethylformamide / 48 h / 20 °C

3.1: 85 percent / pyridine / 4 h / 0 °C

4.1: 81 percent / LiBH₄ / tetrahydrofuran / 7 h / 0 - 20 °C

5.1: 83 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 7 h / 20 °C

6.1: 94 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1 h / 20 °C

7.1: 82 percent / Dess-Martin reagent / CH₂Cl₂ / 6.5 h / 0 - 20 °C

8.1: 45 percent / SmI₂ / tetrahydrofuran / 8 h / 20 °C

With pyridine; sodium hydroxide; lithium borohydride; samarium diiodide; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; Dess-Martin periodane; In tetrahydrofuran; ethanol; dichloromethane; water;
DOI:10.1021/jo026776v

Reference yield:

: 35677-88-4
N-benzyloxycarbonyl-(L)-homoserine

: 511546-71-7
methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-2,6-anhydro-3,5-dideoxy-2-C-{1-[3S-(benzyloxycarbonyl)amino-4-(tetrahydro-2H-pyran-2-yloxy)-1-butanol]}-D-erythro-L-manno-nonanoate

Guidance literature:: Multi-step reaction with 7 steps

1.1: NaOH / H₂O; ethanol / 24 h / 20 °C

1.2: 96 percent / dimethylformamide / 48 h / 20 °C

2.1: 85 percent / pyridine / 4 h / 0 °C

3.1: 81 percent / LiBH₄ / tetrahydrofuran / 7 h / 0 - 20 °C

4.1: 83 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 7 h / 20 °C

5.1: 94 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1 h / 20 °C

6.1: 82 percent / Dess-Martin reagent / CH₂Cl₂ / 6.5 h / 0 - 20 °C

7.1: 45 percent / SmI₂ / tetrahydrofuran / 8 h / 20 °C

With pyridine; sodium hydroxide; lithium borohydride; samarium diiodide; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; Dess-Martin periodane; In tetrahydrofuran; ethanol; dichloromethane; water;
DOI:10.1021/jo026776v