4-(phenylcarboxymethyl)benzyl N-benzyl N-(5-(methyl (2-O-benzoyl-3-O-benzyl-α-L-idopyranosyloxy)uronate)pentyl) carbamate

Base Information

• Chemical Name: 4-(phenylcarboxymethyl)benzyl N-benzyl N-(5-(methyl (2-O-benzoyl-3-O-benzyl-α-L-idopyranosyloxy)uronate)pentyl) carbamate
• CAS No.: 1447802-10-9
• Molecular Formula: C₄₉H₅₁NO₁₂
• Molecular Weight: 845.943
• Mol file: 1447802-10-9.mol

Synonyms:4-(phenylcarboxymethyl)benzyl N-benzyl N-(5-(methyl (2-O-benzoyl-3-O-benzyl-α-L-idopyranosyloxy)uronate)pentyl) carbamate

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

There total 8 articles about 4-(phenylcarboxymethyl)benzyl N-benzyl N-(5-(methyl (2-O-benzoyl-3-O-benzyl-α-L-idopyranosyloxy)uronate)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: 85.0%

4-[(phenylcarboxy)methyl]benzyl N-benzyl-N-[5-(methyl ((2-O-benzoyl-3-O-benzyl-4-O-levulinoyl-α-L-idopyranosyl)oxy)uronate)pentyl]carbamate (1447801-94-6) → 4-(phenylcarboxymethyl)benzyl N-benzyl N-(5-(methyl (2-O-benzoyl-3-O-benzyl-α-L-idopyranosyloxy)uronate)pentyl) carbamate (1447802-10-9)

Guidance literature:

With hydrazinium monoacetate; In methanol; dichloromethane;

DOI:10.1021/jo400467g

Reference yield:

methyl 3-O-benzyl-L-idopyranosyluronate (87326-77-0,87326-78-1) → 4-(phenylcarboxymethyl)benzyl N-benzyl N-(5-(methyl (2-O-benzoyl-3-O-benzyl-α-L-idopyranosyloxy)uronate)pentyl) carbamate (1447802-10-9)

Guidance literature:

Multi-step reaction with 6 steps

1.1: dmap; pyridine / dichloromethane / -40 - 20 °C

2.1: hydrogen bromide / dichloromethane; acetic acid / 3 h / 0 °C

2.2: 20 h / 20 °C / Inert atmosphere

3.1: trimethyltin(IV) hydroxide / toluene / 1 h / 100 °C / Microwave irradiation

3.2: 60 °C / Microwave irradiation

4.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / 5 h / 20 °C

5.1: N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 0 °C

6.1: hydrazinium monoacetate / dichloromethane; methanol

With pyridine; dmap; N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate; hydrogen bromide; hydrazinium monoacetate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; trimethyltin(IV) hydroxide; In methanol; dichloromethane; acetic acid; toluene;

DOI:10.1021/jo400467g

Reference yield:

methyl 1,2,4-tri-O-benzoyl-3-O-benzyl-β-L-idopyranurate (1447801-85-5) → 4-(phenylcarboxymethyl)benzyl N-benzyl N-(5-(methyl (2-O-benzoyl-3-O-benzyl-α-L-idopyranosyloxy)uronate)pentyl) carbamate (1447802-10-9)

Guidance literature:

Multi-step reaction with 5 steps

1.1: hydrogen bromide / dichloromethane; acetic acid / 3 h / 0 °C

1.2: 20 h / 20 °C / Inert atmosphere

2.1: trimethyltin(IV) hydroxide / toluene / 1 h / 100 °C / Microwave irradiation

2.2: 60 °C / Microwave irradiation

3.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / 5 h / 20 °C

4.1: N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 0 °C

5.1: hydrazinium monoacetate / dichloromethane; methanol

With dmap; N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate; hydrogen bromide; hydrazinium monoacetate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; trimethyltin(IV) hydroxide; In methanol; dichloromethane; acetic acid; toluene;

DOI:10.1021/jo400467g

upstream raw materials:

methyl 3-O-benzyl-L-idopyranosyluronate

benzoyl chloride

methyl 1,2,4-tri-O-benzoyl-3-O-benzyl-β-L-idopyranurate

4-((benzyl(5-hydroxypentyl)carbamoyloxy)methyl)benzyl benzoate

Downstream raw materials:

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