Methyl 5-acetamido-4-O-benzyl-3-bromo-3,5-dideoxy-8,9-O-isopropylidene-β-D-erythro-L-manno-2-nonulopyranosonate

Base Information

Chemical Name:Methyl 5-acetamido-4-O-benzyl-3-bromo-3,5-dideoxy-8,9-O-isopropylidene-β-D-erythro-L-manno-2-nonulopyranosonate
CAS No.:353301-96-9
Molecular Formula:C₂₄H₃₂BrNO₁₀
Molecular Weight:574.423
Hs Code.:

Synonyms:Methyl 5-acetamido-4-O-benzyl-3-bromo-3,5-dideoxy-8,9-O-isopropylidene-β-D-erythro-L-manno-2-nonulopyranosonate

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Chemical Property of Methyl 5-acetamido-4-O-benzyl-3-bromo-3,5-dideoxy-8,9-O-isopropylidene-β-D-erythro-L-manno-2-nonulopyranosonate

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Technology Process of Methyl 5-acetamido-4-O-benzyl-3-bromo-3,5-dideoxy-8,9-O-isopropylidene-β-D-erythro-L-manno-2-nonulopyranosonate

There total 4 articles about Methyl 5-acetamido-4-O-benzyl-3-bromo-3,5-dideoxy-8,9-O-isopropylidene-β-D-erythro-L-manno-2-nonulopyranosonate 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:

: (4S,5R,6R)-6-[(S)-Acetoxy-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl]-5-acetylamino-4-benzyloxy-5,6-dihydro-4H-pyran-2-carboxylic acid methyl ester

: 353301-96-9
Methyl 5-acetamido-4-O-benzyl-3-bromo-3,5-dideoxy-8,9-O-isopropylidene-β-D-erythro-L-manno-2-nonulopyranosonate

Guidance literature:: With N-Bromosuccinimide; In water; acetonitrile; at 60 ℃; for 0.166667h;
DOI:10.1002/1521-3765(20010518)7:10<2178::AID-CHEM2178>3.0.CO;2-E

Reference yield:

: 25875-99-4,79026-38-3
methyl 5-acetamido-2,6-anhydro-3,5-dideoxy-D-glycero-D-galacto-non-2-enonate

: 353301-96-9
Methyl 5-acetamido-4-O-benzyl-3-bromo-3,5-dideoxy-8,9-O-isopropylidene-β-D-erythro-L-manno-2-nonulopyranosonate

Guidance literature:: Multi-step reaction with 4 steps

1: 100 percent / TfOH / 3 h / 20 °C

2: 83 percent / NaH / dimethylformamide / 0.17 h / 0 °C

3: pyridine / 2 h

4: 1.85 g / NBS / acetonitrile; H₂O / 0.17 h / 60 °C

With pyridine; N-Bromosuccinimide; trifluorormethanesulfonic acid; sodium hydride; In water; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1002/1521-3765(20010518)7:10<2178::AID-CHEM2178>3.0.CO;2-E

Reference yield:

: 108999-10-6
Methyl 5-acetamido-2,3,5-trideoxy-8,9-O-isopropylidene-D-glycero-D-galacto-non-2-enopyranosonate

: 353301-96-9
Methyl 5-acetamido-4-O-benzyl-3-bromo-3,5-dideoxy-8,9-O-isopropylidene-β-D-erythro-L-manno-2-nonulopyranosonate

Guidance literature:: Multi-step reaction with 3 steps

1: 83 percent / NaH / dimethylformamide / 0.17 h / 0 °C

2: pyridine / 2 h

3: 1.85 g / NBS / acetonitrile; H₂O / 0.17 h / 60 °C

With pyridine; N-Bromosuccinimide; sodium hydride; In water; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1002/1521-3765(20010518)7:10<2178::AID-CHEM2178>3.0.CO;2-E