pent-4-enyl 2-azido 4,6-O-benzylidene 2-deoxy-3-O-(methyl 2,3,4-tri-O-acetyl β-D-glucopyranosyluronate)-β-D-glucopyranoside

Base Information

Chemical Name:pent-4-enyl 2-azido 4,6-O-benzylidene 2-deoxy-3-O-(methyl 2,3,4-tri-O-acetyl β-D-glucopyranosyluronate)-β-D-glucopyranoside
CAS No.:521970-83-2
Molecular Formula:C₃₁H₃₉N₃O₁₄
Molecular Weight:677.662
Hs Code.:

Synonyms:pent-4-enyl 2-azido 4,6-O-benzylidene 2-deoxy-3-O-(methyl 2,3,4-tri-O-acetyl β-D-glucopyranosyluronate)-β-D-glucopyranoside

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Chemical Property of pent-4-enyl 2-azido 4,6-O-benzylidene 2-deoxy-3-O-(methyl 2,3,4-tri-O-acetyl β-D-glucopyranosyluronate)-β-D-glucopyranoside

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Technology Process of pent-4-enyl 2-azido 4,6-O-benzylidene 2-deoxy-3-O-(methyl 2,3,4-tri-O-acetyl β-D-glucopyranosyluronate)-β-D-glucopyranoside

There total 10 articles about pent-4-enyl 2-azido 4,6-O-benzylidene 2-deoxy-3-O-(methyl 2,3,4-tri-O-acetyl β-D-glucopyranosyluronate)-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: 80.0%

: 197895-54-8
methyl (2S,3S,4S,5R,6S)-3,4,5-tris(acetoxy)-6-[(trichloroethanimidoyl)oxy]oxane-2-carboxylate

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

: 521970-83-2
pent-4-enyl 2-azido 4,6-O-benzylidene 2-deoxy-3-O-(methyl 2,3,4-tri-O-acetyl β-D-glucopyranosyluronate)-β-D-glucopyranoside

Guidance literature:: With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 0 - 25 ℃; for 3.5h;
DOI:10.1016/S0040-4039(02)02482-6

Reference yield:

: 72692-06-9,73464-50-3,3082-95-9
methyl 2,3,4-tri-O-acetyl-D-glucopyranuronate

: 521970-83-2
pent-4-enyl 2-azido 4,6-O-benzylidene 2-deoxy-3-O-(methyl 2,3,4-tri-O-acetyl β-D-glucopyranosyluronate)-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 2 steps

1: 60 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / 1,2-dichloro-ethane / 1 h / 0 °C

2: 78 percent / TMSOTf / CH₂Cl₂ / 2.5 h / 0 - 25 °C

With trimethylsilyl trifluoromethanesulfonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; 1,2-dichloro-ethane;
DOI:10.1016/j.tetlet.2007.05.097

Reference yield:

: 2-azido-2-deoxy-D-glucose

: 521970-83-2
pent-4-enyl 2-azido 4,6-O-benzylidene 2-deoxy-3-O-(methyl 2,3,4-tri-O-acetyl β-D-glucopyranosyluronate)-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 7 steps

1: pyridine / 10 h / 0 °C

2: 70 percent / hydrazine acetate / dimethylformamide / 0.75 h / 0 - 25 °C

3: 74 percent / K₂CO₃ / CH₂Cl₂ / 48 h / 25 °C

4: TMSOTf; molecular sieves 4 Angstroem / CH₂Cl₂ / 1 h / 0 °C

5: MeONa / methanol / 6 h / 0 - 25 °C

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

7: 78 percent / TMSOTf / CH₂Cl₂ / 2.5 h / 0 - 25 °C

With pyridine; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; sodium methylate; hydrazinium monoacetate; potassium carbonate; (+)-10-camphorsulfonic acid; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/j.tetlet.2007.05.097