phenyl 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-1-thio-α-L-lyxo-hexopyranoside

Base Information

Chemical Name:phenyl 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-1-thio-α-L-lyxo-hexopyranoside
CAS No.:452071-54-4
Molecular Formula:C₃₃H₃₈N₂O₁₂S
Molecular Weight:686.737
Hs Code.:

phenyl 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-1-thio-α-L-lyxo-hexopyranoside

Synonyms:phenyl 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-1-thio-α-L-lyxo-hexopyranoside

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Chemical Property of phenyl 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-1-thio-α-L-lyxo-hexopyranoside

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Technology Process of phenyl 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-1-thio-α-L-lyxo-hexopyranoside

There total 10 articles about phenyl 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-1-thio-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: 54.0%

: 4551-15-9
phenylthiotrimethylsilane

: 195865-25-9
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-1-O-p-nitrobenzoyl-α-L-lyxo-hexopyranoside

: 452071-54-4
phenyl 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-1-thio-α-L-lyxo-hexopyranoside

Guidance literature:: With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 0 ℃; for 1h;
DOI:10.1016/S0968-0896(01)00411-4

Reference yield:

: 196512-07-9
3-N-allyloxycarbonyl-1,4-di-O-p-nitrobenzoyl-3-amino-2,3,6-trideoxy-α-L-lyxo-hexopyranose

: 452071-54-4
phenyl 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-1-thio-α-L-lyxo-hexopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1.1: 95 percent / CF₃SO₃SiMe₃ / CH₂Cl₂ / 2 h / 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

With pyridine; ammonium cerium(IV) nitrate; trimethylsilyl trifluoromethanesulfonate; iodonium di(2,4,6-trimethylpyridine) perchlorate; 4 A molecular sieve; In diethyl ether; dichloromethane; water; 1,2-dichloro-ethane; acetonitrile;
DOI:10.1016/S0968-0896(01)00411-4

Reference yield:

: 54621-94-2
3,4-di-O-acetyl-L-fucal

: 452071-54-4
phenyl 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-1-thio-α-L-lyxo-hexopyranoside

Guidance literature:: Multi-step reaction with 7 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

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