pent-4-enyl 2-azido-2-deoxy-3-O-acetyl-4,6-O-benzylidene-β-D-glucopyranoside

Base Information

Chemical Name:pent-4-enyl 2-azido-2-deoxy-3-O-acetyl-4,6-O-benzylidene-β-D-glucopyranoside
CAS No.:824967-40-0
Molecular Formula:C₂₀H₂₅N₃O₆
Molecular Weight:403.435
Hs Code.:

Synonyms:pent-4-enyl 2-azido-2-deoxy-3-O-acetyl-4,6-O-benzylidene-β-D-glucopyranoside

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Chemical Property of pent-4-enyl 2-azido-2-deoxy-3-O-acetyl-4,6-O-benzylidene-β-D-glucopyranoside

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Technology Process of pent-4-enyl 2-azido-2-deoxy-3-O-acetyl-4,6-O-benzylidene-β-D-glucopyranoside

There total 6 articles about pent-4-enyl 2-azido-2-deoxy-3-O-acetyl-4,6-O-benzylidene-β-D-glucopyranoside 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: 86.0%

: 75-36-5
acetyl chloride

: 325704-78-7
pent-4-enyl 2-azido 2-deoxy-4,6-O-bennzylidene β-D-glucopyranoside

: 824967-40-0
pent-4-enyl 2-azido-2-deoxy-3-O-acetyl-4,6-O-benzylidene-β-D-glucopyranoside

Guidance literature:: With pyridine; at 25 ℃; for 15h;
DOI:10.1021/jo049092r

Reference yield:

: 3,4,6-tri-O-acetyl-2-azido-2-deoxy-D-glucopyranose

: 824967-40-0
pent-4-enyl 2-azido-2-deoxy-3-O-acetyl-4,6-O-benzylidene-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1: 74 percent / K₂CO₃ / CH₂Cl₂ / 48 h / 25 °C

2: TMSOTf / CH₂Cl₂ / 1 h / 0 °C

3: 3.56 g / methanol; NaOMe / 6 h / 25 °C

4: (+)-camphorsulfonic acid / tetrahydrofuran / 6 h / Heating

5: 86 percent / pyridine / 15 h / 25 °C

With pyridine; methanol; trimethylsilyl trifluoromethanesulfonate; sodium methylate; potassium carbonate; (+)-10-camphorsulfonic acid; In tetrahydrofuran; dichloromethane;
DOI:10.1021/jo049092r

Reference yield:

: 171032-74-9
1,3,4,6-tetra-O-acetyl-2-azido-2-deoxy-D-glucopyranose

: 824967-40-0
pent-4-enyl 2-azido-2-deoxy-3-O-acetyl-4,6-O-benzylidene-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 6 steps

1: 70 percent / hydrazine acetate / dimethylformamide / 0.75 h / 0 - 25 °C

2: 74 percent / K₂CO₃ / CH₂Cl₂ / 48 h / 25 °C

3: TMSOTf / CH₂Cl₂ / 1 h / 0 °C

4: 3.56 g / methanol; NaOMe / 6 h / 25 °C

5: (+)-camphorsulfonic acid / tetrahydrofuran / 6 h / Heating

6: 86 percent / pyridine / 15 h / 25 °C

With pyridine; methanol; trimethylsilyl trifluoromethanesulfonate; sodium methylate; hydrazinium monoacetate; potassium carbonate; (+)-10-camphorsulfonic acid; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo049092r