p-methoxybenzyl 4-O-(3-N,4-O-di-allyloxycarbonyl-3-amino-2,3,6-trideoxy-α-L-arabino-hexopyranosyl)-2,3,6-trideoxy-α-L-lyxo-hexopyranoside

Base Information

• Chemical Name: p-methoxybenzyl 4-O-(3-N,4-O-di-allyloxycarbonyl-3-amino-2,3,6-trideoxy-α-L-arabino-hexopyranosyl)-2,3,6-trideoxy-α-L-lyxo-hexopyranoside
• CAS No.: 452071-65-7
• Molecular Formula: C₂₈H₃₉NO₁₀
• Molecular Weight: 549.618
• Mol file: 452071-65-7.mol

Synonyms:p-methoxybenzyl 4-O-(3-N,4-O-di-allyloxycarbonyl-3-amino-2,3,6-trideoxy-α-L-arabino-hexopyranosyl)-2,3,6-trideoxy-α-L-lyxo-hexopyranoside

Chemical Property of p-methoxybenzyl 4-O-(3-N,4-O-di-allyloxycarbonyl-3-amino-2,3,6-trideoxy-α-L-arabino-hexopyranosyl)-2,3,6-trideoxy-α-L-lyxo-hexopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of p-methoxybenzyl 4-O-(3-N,4-O-di-allyloxycarbonyl-3-amino-2,3,6-trideoxy-α-L-arabino-hexopyranosyl)-2,3,6-trideoxy-α-L-lyxo-hexopyranoside

There total 10 articles about p-methoxybenzyl 4-O-(3-N,4-O-di-allyloxycarbonyl-3-amino-2,3,6-trideoxy-α-L-arabino-hexopyranosyl)-2,3,6-trideoxy-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: 75.0%

p-methoxybenzyl 2,3,6-trideoxy-α-L-lyxo-hexopyranoside (452071-62-4) + phenyl 3-N,4-O-di-allyloxycarbonyl-3-amino-1-thio-2,3,6-trideoxy-α-L-arabino-hexopyranoside (452071-48-6) → p-methoxybenzyl 4-O-(3-N,4-O-di-allyloxycarbonyl-3-amino-2,3,6-trideoxy-α-L-arabino-hexopyranosyl)-2,3,6-trideoxy-α-L-lyxo-hexopyranoside (452071-65-7)

Guidance literature:

p-methoxybenzyl 2,3,6-trideoxy-α-L-lyxo-hexopyranoside; phenyl 3-N,4-O-di-allyloxycarbonyl-3-amino-1-thio-2,3,6-trideoxy-α-L-arabino-hexopyranoside; With iodonium di(2,4,6-trimethylpyridine) perchlorate; 4 A molecular sieve; In diethyl ether; 1,2-dichloro-ethane; at 10 ℃; for 1h;

With triphenylphosphine; In diethyl ether; 1,2-dichloro-ethane; for 1h;

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

Reference yield:

4-Methoxybenzyl alcohol (105-13-5) → p-methoxybenzyl 4-O-(3-N,4-O-di-allyloxycarbonyl-3-amino-2,3,6-trideoxy-α-L-arabino-hexopyranosyl)-2,3,6-trideoxy-α-L-lyxo-hexopyranoside (452071-65-7)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 70 percent / SnCl₄ / CH₂Cl₂ / 2 h / 0 °C

2.1: 90 percent / H₂ / (Ph₃P)3RhCl / benzene / 2 h / 760 Torr

3.1: 60 percent / NaOMe / methanol / 2 h / 20 °C

4.1: 50 percent / Ph₃P; DEAD / tetrahydrofuran / 2 h / 20 °C

5.1: 94 percent / K₂CO₃ / methanol / 2 h / 20 °C

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

6.2: 75 percent / Ph₃P / diethyl ether; 1,2-dichloro-ethane / 1 h

With iodonium di(2,4,6-trimethylpyridine) perchlorate; 4 A molecular sieve; hydrogen; sodium methylate; tin(IV) chloride; potassium carbonate; triphenylphosphine; diethylazodicarboxylate; Wilkinson's catalyst; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; 1,2-dichloro-ethane; benzene;

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

Reference yield:

methyl-3-amino-2,3,6-tridesoxy-α-L-arabino-hexopyranoside (54623-23-3) → p-methoxybenzyl 4-O-(3-N,4-O-di-allyloxycarbonyl-3-amino-2,3,6-trideoxy-α-L-arabino-hexopyranosyl)-2,3,6-trideoxy-α-L-lyxo-hexopyranoside (452071-65-7)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 70 percent / pyridine / CH₂Cl₂ / 4 h / 20 °C

2.1: 94 percent / CF₃SO₃SiMe₃ / CH₂Cl₂ / 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: 75 percent / Ph₃P / diethyl ether; 1,2-dichloro-ethane / 1 h

With pyridine; trimethylsilyl trifluoromethanesulfonate; iodonium di(2,4,6-trimethylpyridine) perchlorate; 4 A molecular sieve; In diethyl ether; dichloromethane; 1,2-dichloro-ethane;

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

upstream raw materials:

p-methoxybenzyl 2,3,6-trideoxy-α-L-lyxo-hexopyranoside

phenyl 3-N,4-O-di-allyloxycarbonyl-3-amino-1-thio-2,3,6-trideoxy-α-L-arabino-hexopyranoside

methyl-3-amino-2,3,6-tridesoxy-α-L-arabino-hexopyranoside

4-Methoxybenzyl alcohol

Downstream raw materials:

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

Refernces