4-O-[4-O-(3-N-allyloxycarbonyl-3-amino-2,3,6-trideoxy-4-O-p-nitrobenzoyl-α-L-lyxo-hexopyranosyl)-3-O-allyloxycarbonyl-2,6-dideoxy-α-L-lyxo-hexopyranosyl]-3-O-allyloxycarbonyl-2,6-dideoxy-1-O-p-nitrobenzoyl-α-L-lyxo-hexopyranoside

Base Information

• Chemical Name: 4-O-[4-O-(3-N-allyloxycarbonyl-3-amino-2,3,6-trideoxy-4-O-p-nitrobenzoyl-α-L-lyxo-hexopyranosyl)-3-O-allyloxycarbonyl-2,6-dideoxy-α-L-lyxo-hexopyranosyl]-3-O-allyloxycarbonyl-2,6-dideoxy-1-O-p-nitrobenzoyl-α-L-lyxo-hexopyranoside
• CAS No.: 452071-56-6
• Molecular Formula: C₄₄H₅₁N₃O₂₁
• Molecular Weight: 957.896

Synonyms:4-O-[4-O-(3-N-allyloxycarbonyl-3-amino-2,3,6-trideoxy-4-O-p-nitrobenzoyl-α-L-lyxo-hexopyranosyl)-3-O-allyloxycarbonyl-2,6-dideoxy-α-L-lyxo-hexopyranosyl]-3-O-allyloxycarbonyl-2,6-dideoxy-1-O-p-nitrobenzoyl-α-L-lyxo-hexopyranoside

Chemical Property of 4-O-[4-O-(3-N-allyloxycarbonyl-3-amino-2,3,6-trideoxy-4-O-p-nitrobenzoyl-α-L-lyxo-hexopyranosyl)-3-O-allyloxycarbonyl-2,6-dideoxy-α-L-lyxo-hexopyranosyl]-3-O-allyloxycarbonyl-2,6-dideoxy-1-O-p-nitrobenzoyl-α-L-lyxo-hexopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

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MSDS Files:

Useful:

Technology Process of 4-O-[4-O-(3-N-allyloxycarbonyl-3-amino-2,3,6-trideoxy-4-O-p-nitrobenzoyl-α-L-lyxo-hexopyranosyl)-3-O-allyloxycarbonyl-2,6-dideoxy-α-L-lyxo-hexopyranosyl]-3-O-allyloxycarbonyl-2,6-dideoxy-1-O-p-nitrobenzoyl-α-L-lyxo-hexopyranoside

There total 13 articles about 4-O-[4-O-(3-N-allyloxycarbonyl-3-amino-2,3,6-trideoxy-4-O-p-nitrobenzoyl-α-L-lyxo-hexopyranosyl)-3-O-allyloxycarbonyl-2,6-dideoxy-α-L-lyxo-hexopyranosyl]-3-O-allyloxycarbonyl-2,6-dideoxy-1-O-p-nitrobenzoyl-α-L-lyxo-hexopyranoside 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:

3,4-di-O-acetyl-L-fucal (54621-94-2) → 4-O-[4-O-(3-N-allyloxycarbonyl-3-amino-2,3,6-trideoxy-4-O-p-nitrobenzoyl-α-L-lyxo-hexopyranosyl)-3-O-allyloxycarbonyl-2,6-dideoxy-α-L-lyxo-hexopyranosyl]-3-O-allyloxycarbonyl-2,6-dideoxy-1-O-p-nitrobenzoyl-α-L-lyxo-hexopyranoside (452071-56-6)

Guidance literature:

Multi-step reaction with 10 steps

1.1: 9 g / Ph₃P*HBr / CH₂Cl₂ / 1 h / 20 °C

2.1: 3.5 g / MeONa / methanol / 2 h / 20 °C

3.1: Bu₂SnO / toluene / 12 h / Heating

3.2: Et₃N / toluene / 2 h / -45 °C

3.3: 62 percent / oxalic acid / toluene; acetonitrile / -78 - 20 °C

4.1: molecular sieves 4 Angstroem; iodonium dicollidine perchlorate / diethyl ether; 1,2-dichloro-ethane / 1 h / 10 °C

4.2: 74 percent / Ph₃P / diethyl ether; 1,2-dichloro-ethane / 1 h

5.1: 100 percent / Ce(NH₄)2(NO₃)6 / acetonitrile; H₂O / 2 h / 20 °C

6.1: pyridine / 2 h / 0 °C

7.1: 54 percent / CF₃SO₃SiMe₃ / CH₂Cl₂ / 1 h / 0 °C

8.1: 41 percent / molecular sieves 4 Angstroem; iodonium dicollidine perchlorate / diethyl ether; 1,2-dichloro-ethane / 1.5 h / 10 °C

9.1: 100 percent / Ce(NH₄)2(NO₃)6 / acetonitrile; H₂O / 2 h / 20 °C

10.1: pyridine / 2 h / 0 °C

With pyridine; ammonium cerium(IV) nitrate; trimethylsilyl trifluoromethanesulfonate; iodonium di(2,4,6-trimethylpyridine) perchlorate; 4 A molecular sieve; sodium methylate; triphenylphosphine hydrobromide; di(n-butyl)tin oxide; In methanol; diethyl ether; dichloromethane; water; 1,2-dichloro-ethane; toluene; acetonitrile;

DOI:10.1016/S0968-0896(01)00411-4

Reference yield:

p-methoxybenzyl 2,6-dideoxy-α-L-lyxo-hexopyranoside (452071-50-0) → 4-O-[4-O-(3-N-allyloxycarbonyl-3-amino-2,3,6-trideoxy-4-O-p-nitrobenzoyl-α-L-lyxo-hexopyranosyl)-3-O-allyloxycarbonyl-2,6-dideoxy-α-L-lyxo-hexopyranosyl]-3-O-allyloxycarbonyl-2,6-dideoxy-1-O-p-nitrobenzoyl-α-L-lyxo-hexopyranoside (452071-56-6)

Guidance literature:

Multi-step reaction with 8 steps

1.1: Bu₂SnO / toluene / 12 h / Heating

1.2: Et₃N / toluene / 2 h / -45 °C

1.3: 62 percent / oxalic acid / toluene; acetonitrile / -78 - 20 °C

2.1: molecular sieves 4 Angstroem; iodonium dicollidine perchlorate / diethyl ether; 1,2-dichloro-ethane / 1 h / 10 °C

2.2: 74 percent / Ph₃P / diethyl ether; 1,2-dichloro-ethane / 1 h

3.1: 100 percent / Ce(NH₄)2(NO₃)6 / acetonitrile; H₂O / 2 h / 20 °C

4.1: pyridine / 2 h / 0 °C

5.1: 54 percent / CF₃SO₃SiMe₃ / CH₂Cl₂ / 1 h / 0 °C

6.1: 41 percent / molecular sieves 4 Angstroem; iodonium dicollidine perchlorate / diethyl ether; 1,2-dichloro-ethane / 1.5 h / 10 °C

7.1: 100 percent / Ce(NH₄)2(NO₃)6 / acetonitrile; H₂O / 2 h / 20 °C

8.1: pyridine / 2 h / 0 °C

With pyridine; ammonium cerium(IV) nitrate; trimethylsilyl trifluoromethanesulfonate; iodonium di(2,4,6-trimethylpyridine) perchlorate; 4 A molecular sieve; di(n-butyl)tin oxide; In diethyl ether; dichloromethane; water; 1,2-dichloro-ethane; toluene; acetonitrile;

DOI:10.1016/S0968-0896(01)00411-4

Reference yield:

p-methoxybenzyl 3,4-di-O-acetyl-2,6-dideoxy-α-L-lyxo-hexopyranoside (452071-49-7) → 4-O-[4-O-(3-N-allyloxycarbonyl-3-amino-2,3,6-trideoxy-4-O-p-nitrobenzoyl-α-L-lyxo-hexopyranosyl)-3-O-allyloxycarbonyl-2,6-dideoxy-α-L-lyxo-hexopyranosyl]-3-O-allyloxycarbonyl-2,6-dideoxy-1-O-p-nitrobenzoyl-α-L-lyxo-hexopyranoside (452071-56-6)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 3.5 g / MeONa / methanol / 2 h / 20 °C

2.1: Bu₂SnO / toluene / 12 h / Heating

2.2: Et₃N / toluene / 2 h / -45 °C

2.3: 62 percent / oxalic acid / toluene; acetonitrile / -78 - 20 °C

3.1: molecular sieves 4 Angstroem; iodonium dicollidine perchlorate / diethyl ether; 1,2-dichloro-ethane / 1 h / 10 °C

3.2: 74 percent / Ph₃P / diethyl ether; 1,2-dichloro-ethane / 1 h

4.1: 100 percent / Ce(NH₄)2(NO₃)6 / acetonitrile; H₂O / 2 h / 20 °C

5.1: pyridine / 2 h / 0 °C

6.1: 54 percent / CF₃SO₃SiMe₃ / CH₂Cl₂ / 1 h / 0 °C

7.1: 41 percent / molecular sieves 4 Angstroem; iodonium dicollidine perchlorate / diethyl ether; 1,2-dichloro-ethane / 1.5 h / 10 °C

8.1: 100 percent / Ce(NH₄)2(NO₃)6 / acetonitrile; H₂O / 2 h / 20 °C

9.1: pyridine / 2 h / 0 °C

With pyridine; ammonium cerium(IV) nitrate; trimethylsilyl trifluoromethanesulfonate; iodonium di(2,4,6-trimethylpyridine) perchlorate; 4 A molecular sieve; sodium methylate; di(n-butyl)tin oxide; In methanol; diethyl ether; dichloromethane; water; 1,2-dichloro-ethane; toluene; acetonitrile;

DOI:10.1016/S0968-0896(01)00411-4

upstream raw materials:

4-nitro-benzoyl chloride

3-N-allyloxycarbonyl-1,4-di-O-p-nitrobenzoyl-3-amino-2,3,6-trideoxy-α-L-lyxo-hexopyranose

3,4-di-O-acetyl-L-fucal

p-methoxybenzyl 2,6-dideoxy-α-L-lyxo-hexopyranoside

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