7-[4-O-(3-amino-2,3,6-trideoxy-3-N-allyloxycarbonyl-4-O-p-nitrobenzoyl-α-L-lyxo-hexopyranosyl)-2,3,6-trideoxy-α-L-lyxo-hexopyranosyl]-14-acetoxy-4-demethoxyadriamycinone

Base Information

Chemical Name:7-[4-O-(3-amino-2,3,6-trideoxy-3-N-allyloxycarbonyl-4-O-p-nitrobenzoyl-α-L-lyxo-hexopyranosyl)-2,3,6-trideoxy-α-L-lyxo-hexopyranosyl]-14-acetoxy-4-demethoxyadriamycinone
CAS No.:452071-69-1
Molecular Formula:C₄₅H₄₆N₂O₁₈
Molecular Weight:902.863
Hs Code.:

7-[4-O-(3-amino-2,3,6-trideoxy-3-N-allyloxycarbonyl-4-O-p-nitrobenzoyl-α-L-lyxo-hexopyranosyl)-2,3,6-trideoxy-α-L-lyxo-hexopyranosyl]-14-acetoxy-4-demethoxyadriamycinone

Synonyms:7-[4-O-(3-amino-2,3,6-trideoxy-3-N-allyloxycarbonyl-4-O-p-nitrobenzoyl-α-L-lyxo-hexopyranosyl)-2,3,6-trideoxy-α-L-lyxo-hexopyranosyl]-14-acetoxy-4-demethoxyadriamycinone

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Chemical Property of 7-[4-O-(3-amino-2,3,6-trideoxy-3-N-allyloxycarbonyl-4-O-p-nitrobenzoyl-α-L-lyxo-hexopyranosyl)-2,3,6-trideoxy-α-L-lyxo-hexopyranosyl]-14-acetoxy-4-demethoxyadriamycinone

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Technology Process of 7-[4-O-(3-amino-2,3,6-trideoxy-3-N-allyloxycarbonyl-4-O-p-nitrobenzoyl-α-L-lyxo-hexopyranosyl)-2,3,6-trideoxy-α-L-lyxo-hexopyranosyl]-14-acetoxy-4-demethoxyadriamycinone

There total 11 articles about 7-[4-O-(3-amino-2,3,6-trideoxy-3-N-allyloxycarbonyl-4-O-p-nitrobenzoyl-α-L-lyxo-hexopyranosyl)-2,3,6-trideoxy-α-L-lyxo-hexopyranosyl]-14-acetoxy-4-demethoxyadriamycinone 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: 45.0%

: 91383-39-0
(+)-14-Acetoxy-4-demethoxydaunomicinone

: 452071-64-6
4-O-(3-N-allyloxycarbonyl-4-O-p-nitrobenzoyl-3-amino-2,3,6-trideoxy-α-L-lyxo-hexopyranosyl)-2,3,6-trideoxy-1-O-p-nitrobenzoyl-α-L-lyxo-hexopyranoside

: 452071-69-1
7-[4-O-(3-amino-2,3,6-trideoxy-3-N-allyloxycarbonyl-4-O-p-nitrobenzoyl-α-L-lyxo-hexopyranosyl)-2,3,6-trideoxy-α-L-lyxo-hexopyranosyl]-14-acetoxy-4-demethoxyadriamycinone

Guidance literature:: With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; In diethyl ether; dichloromethane; at -30 ℃; for 1.5h;
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

: 452071-69-1
7-[4-O-(3-amino-2,3,6-trideoxy-3-N-allyloxycarbonyl-4-O-p-nitrobenzoyl-α-L-lyxo-hexopyranosyl)-2,3,6-trideoxy-α-L-lyxo-hexopyranosyl]-14-acetoxy-4-demethoxyadriamycinone

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

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

4.1: pyridine / 2 h / 0 °C

5.1: 45 percent / molecular sieves 4 Angstroem; TMSOTf / CH₂Cl₂; diethyl ether / 1.5 h / -30 °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:

: 452071-59-9
p-methoxybenzyl 2,3,6-trideoxy-α-L-arabino-hexopyranoside

: 452071-69-1
7-[4-O-(3-amino-2,3,6-trideoxy-3-N-allyloxycarbonyl-4-O-p-nitrobenzoyl-α-L-lyxo-hexopyranosyl)-2,3,6-trideoxy-α-L-lyxo-hexopyranosyl]-14-acetoxy-4-demethoxyadriamycinone

Guidance literature:: Multi-step reaction with 6 steps

1.1: 50 percent / Ph₃P; DEAD / tetrahydrofuran / 2 h / 20 °C

2.1: 94 percent / K₂CO₃ / methanol / 2 h / 20 °C

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

3.2: 84 percent / Ph₃P / diethyl ether; 1,2-dichloro-ethane / 1 h

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

5.1: pyridine / 2 h / 0 °C

6.1: 45 percent / molecular sieves 4 Angstroem; TMSOTf / CH₂Cl₂; diethyl ether / 1.5 h / -30 °C

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