pent-4-enyl 2-azido-2-deoxy-4,6-O-benzylidene-α-D-glucopyranoside

Base Information

Chemical Name:pent-4-enyl 2-azido-2-deoxy-4,6-O-benzylidene-α-D-glucopyranoside
CAS No.:619328-24-4
Molecular Formula:C₁₈H₂₃N₃O₅
Molecular Weight:361.398
Hs Code.:

Synonyms:pent-4-enyl 2-azido-2-deoxy-4,6-O-benzylidene-α-D-glucopyranoside

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

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

There total 6 articles about pent-4-enyl 2-azido-2-deoxy-4,6-O-benzylidene-α-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:

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

: 619328-24-4
pent-4-enyl 2-azido-2-deoxy-4,6-O-benzylidene-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 6 steps

1: 11.5 g / pyridine / 10 h / 0 - 4 °C

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

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

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

5: 3.56 g / NaOMe / methanol / 0 h / 25 °C

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

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/S0040-4020(02)01567-3

Reference yield:

: 1078691-95-8
(+)-D-glucosamine hydrochloride

: 619328-24-4
pent-4-enyl 2-azido-2-deoxy-4,6-O-benzylidene-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 7 steps

1.1: NaOMe / methanol / 0.5 h

1.2: TfN₃; DMAP / methanol; CH₂Cl₂ / 18 h / 25 °C

2.1: 11.5 g / pyridine / 10 h / 0 - 4 °C

3.1: 70 percent / hydrazine acetate / dimethylformamide / 0.75 h / 0 - 25 °C

4.1: 74 percent / K₂CO₃ / CH₂Cl₂ / 48 h / 25 °C

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

6.1: 3.56 g / NaOMe / methanol / 0 h / 25 °C

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

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/S0040-4020(02)01567-3

Reference yield:

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

: 619328-24-4
pent-4-enyl 2-azido-2-deoxy-4,6-O-benzylidene-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 4 steps

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

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

3: 3.56 g / NaOMe / methanol / 0 h / 25 °C

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

With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; sodium methylate; potassium carbonate; (+)-10-camphorsulfonic acid; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1016/S0040-4020(02)01567-3