4-(phenylcarboxymethyl)benzyl N-benzyl N-(5-(2-O-benzoyl-3-O-benzyl-6-O-para-methoxybenzyl-α-L-idopyranosyloxy)pentyl)carbamate

Base Information

• Chemical Name: 4-(phenylcarboxymethyl)benzyl N-benzyl N-(5-(2-O-benzoyl-3-O-benzyl-6-O-para-methoxybenzyl-α-L-idopyranosyloxy)pentyl)carbamate
• CAS No.: 1447802-04-1
• Molecular Formula: C₅₆H₅₉NO₁₂
• Molecular Weight: 938.084
• Mol file: 1447802-04-1.mol

Synonyms:4-(phenylcarboxymethyl)benzyl N-benzyl N-(5-(2-O-benzoyl-3-O-benzyl-6-O-para-methoxybenzyl-α-L-idopyranosyloxy)pentyl)carbamate

Chemical Property of 4-(phenylcarboxymethyl)benzyl N-benzyl N-(5-(2-O-benzoyl-3-O-benzyl-6-O-para-methoxybenzyl-α-L-idopyranosyloxy)pentyl)carbamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-(phenylcarboxymethyl)benzyl N-benzyl N-(5-(2-O-benzoyl-3-O-benzyl-6-O-para-methoxybenzyl-α-L-idopyranosyloxy)pentyl)carbamate

There total 5 articles about 4-(phenylcarboxymethyl)benzyl N-benzyl N-(5-(2-O-benzoyl-3-O-benzyl-6-O-para-methoxybenzyl-α-L-idopyranosyloxy)pentyl)carbamate 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: 86.0%

4-[(phenylcarboxy)methyl]benzyl N-benzyl-N-[5-((2-O-benzoyl-3-O-benzyl-4-O-levulinoyl-6-O-(p-methoxybenzyl)-α-L-idopyranosyl)oxy)pentyl]carbamate (1447801-91-3) → 4-(phenylcarboxymethyl)benzyl N-benzyl N-(5-(2-O-benzoyl-3-O-benzyl-6-O-para-methoxybenzyl-α-L-idopyranosyloxy)pentyl)carbamate (1447802-04-1)

Guidance literature:

With hydrazinium monoacetate; In methanol; dichloromethane;

DOI:10.1021/jo400467g

Reference yield:

phenyl 2-O-benzoyl-3-O-benzyl-4-O-levulinoyl-6-O-(p-methoxyphenyl)-1-thio-α-L-idopyranoside (1447801-78-6) → 4-(phenylcarboxymethyl)benzyl N-benzyl N-(5-(2-O-benzoyl-3-O-benzyl-6-O-para-methoxybenzyl-α-L-idopyranosyloxy)pentyl)carbamate (1447802-04-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / 5 h / 20 °C

2: N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate / dichloromethane / -20 - 20 °C / Inert atmosphere

3: hydrazinium monoacetate / dichloromethane; methanol

With dmap; N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate; hydrazinium monoacetate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In methanol; dichloromethane;

DOI:10.1021/jo400467g

Reference yield:

C21H22O6 → 4-(phenylcarboxymethyl)benzyl N-benzyl N-(5-(2-O-benzoyl-3-O-benzyl-6-O-para-methoxybenzyl-α-L-idopyranosyloxy)pentyl)carbamate (1447802-04-1)

Guidance literature:

Multi-step reaction with 5 steps

1: zinc(II) iodide / dichloromethane / 20 °C

2: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 20 °C

3: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / 5 h / 20 °C

4: N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate / dichloromethane / -20 - 20 °C / Inert atmosphere

5: hydrazinium monoacetate / dichloromethane; methanol

With dmap; N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate; di-isopropyl azodicarboxylate; hydrazinium monoacetate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triphenylphosphine; zinc(II) iodide; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1021/jo400467g

upstream raw materials:

phenyl 2-O-benzoyl-3-O-benzyl-4-O-levulinoyl-6-O-(p-methoxyphenyl)-1-thio-α-L-idopyranoside

phenyl 2-O-benzoyl-3-O-benzyl-4,6-dihydroxylthio-α-L-idopyranoside

phenyl 2-O-benzoyl-3-O-benzyl-4-O-levulinoyl-6-O-(p-methoxyphenyl)-1-thio-α-L-idopyranoside

4-[(phenylcarboxy)methyl]benzyl N-benzyl-N-[5-((2-O-benzoyl-3-O-benzyl-4-O-levulinoyl-6-O-(p-methoxybenzyl)-α-L-idopyranosyl)oxy)pentyl]carbamate

Downstream raw materials:

4-[(phenylcarboxy)methyl]benzyl N-benzyl-N-[5-((4-O-(2-azido-3-O-benzyl-6-O-benzoyl-2-deoxy-4-O-levulinoyl-α-D-glucopyranosyl)-3-O-benzyl-2-O-benzoyl-6-O-(p-methoxybenzyl)-α-L-idopyranosyl)oxy)pentyl]carbamate