4-(1,3-dioxolan-2-yl)-3-oxabutyl 2-O-(4-azido-3-O-benzyl-2-O-methyl-4,6-dideoxy-α-D-mannopyranosyl)-4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranoside

Base Information

Chemical Name:4-(1,3-dioxolan-2-yl)-3-oxabutyl 2-O-(4-azido-3-O-benzyl-2-O-methyl-4,6-dideoxy-α-D-mannopyranosyl)-4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranoside
CAS No.:219838-70-7
Molecular Formula:C₃₃H₄₄N₆O₁₀
Molecular Weight:684.747
Hs Code.:

4-(1,3-dioxolan-2-yl)-3-oxabutyl 2-O-(4-azido-3-O-benzyl-2-O-methyl-4,6-dideoxy-α-D-mannopyranosyl)-4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranoside

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Chemical Property of 4-(1,3-dioxolan-2-yl)-3-oxabutyl 2-O-(4-azido-3-O-benzyl-2-O-methyl-4,6-dideoxy-α-D-mannopyranosyl)-4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranoside

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Technology Process of 4-(1,3-dioxolan-2-yl)-3-oxabutyl 2-O-(4-azido-3-O-benzyl-2-O-methyl-4,6-dideoxy-α-D-mannopyranosyl)-4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranoside

There total 7 articles about 4-(1,3-dioxolan-2-yl)-3-oxabutyl 2-O-(4-azido-3-O-benzyl-2-O-methyl-4,6-dideoxy-α-D-mannopyranosyl)-4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranoside 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:

: 117107-69-4
1,2-Di-O-acetyl-4-azido-4,6-dideoxy-3-O-benzyl-α-D-mannopyranoside

: 219838-70-7
4-(1,3-dioxolan-2-yl)-3-oxabutyl 2-O-(4-azido-3-O-benzyl-2-O-methyl-4,6-dideoxy-α-D-mannopyranosyl)-4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranoside

Guidance literature:: Multi-step reaction with 7 steps

1: 2-aminoethanol / ethyl acetate / 4 h

2: K₂CO₃ / CH₂Cl₂ / 24 h

3: 68 percent / molecular sieves 4 Angstroem, trimethylsilyl triflate / CH₂Cl₂ / 0.25 h

4: sodium methoxide / methanol / 1 h / Ambient temperature

5: 54 percent / molecular sieves, trimethylsilyl triflate / CH₂Cl₂ / -60 - 25 °C

6: sodium methoxide / methanol / 1 h / Ambient temperature

7: 1.) NaH / 1) N,N-dimethylformamide, 0 deg C, 30 min; 2) N,N-dimethylformamide, 25 deg C, 24 h

With molecular sieve; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; sodium methylate; sodium hydride; potassium carbonate; ethanolamine; In methanol; dichloromethane; ethyl acetate;
DOI:10.1080/07328309808002355

Reference yield:

: Acetic acid (2S,3S,4S,5R,6R)-5-azido-4-benzyloxy-2-hydroxy-6-methyl-tetrahydro-pyran-3-yl ester

: 219838-70-7
4-(1,3-dioxolan-2-yl)-3-oxabutyl 2-O-(4-azido-3-O-benzyl-2-O-methyl-4,6-dideoxy-α-D-mannopyranosyl)-4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranoside

Guidance literature:: Multi-step reaction with 6 steps

1: K₂CO₃ / CH₂Cl₂ / 24 h

2: 68 percent / molecular sieves 4 Angstroem, trimethylsilyl triflate / CH₂Cl₂ / 0.25 h

3: sodium methoxide / methanol / 1 h / Ambient temperature

4: 54 percent / molecular sieves, trimethylsilyl triflate / CH₂Cl₂ / -60 - 25 °C

5: sodium methoxide / methanol / 1 h / Ambient temperature

6: 1.) NaH / 1) N,N-dimethylformamide, 0 deg C, 30 min; 2) N,N-dimethylformamide, 25 deg C, 24 h

With molecular sieve; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; sodium methylate; sodium hydride; potassium carbonate; In methanol; dichloromethane;
DOI:10.1080/07328309808002355

Reference yield:

: 219838-56-9
2-O-acetyl-4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranosyl trichloroacetimidate

: 219838-70-7
4-(1,3-dioxolan-2-yl)-3-oxabutyl 2-O-(4-azido-3-O-benzyl-2-O-methyl-4,6-dideoxy-α-D-mannopyranosyl)-4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1: 68 percent / molecular sieves 4 Angstroem, trimethylsilyl triflate / CH₂Cl₂ / 0.25 h

2: sodium methoxide / methanol / 1 h / Ambient temperature

3: 54 percent / molecular sieves, trimethylsilyl triflate / CH₂Cl₂ / -60 - 25 °C

4: sodium methoxide / methanol / 1 h / Ambient temperature

5: 1.) NaH / 1) N,N-dimethylformamide, 0 deg C, 30 min; 2) N,N-dimethylformamide, 25 deg C, 24 h

With molecular sieve; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; sodium methylate; sodium hydride; In methanol; dichloromethane;
DOI:10.1080/07328309808002355