benzyl((2S,3S)-1-(2,4-dimethoxybenzyl)-2-(hydroxymethyl)-4-oxoazetidin-3-yl)carbamate

Base Information

• Chemical Name: benzyl((2S,3S)-1-(2,4-dimethoxybenzyl)-2-(hydroxymethyl)-4-oxoazetidin-3-yl)carbamate
• CAS No.: 86334-63-6
• Molecular Formula: C₂₁H₂₄N₂O₆
• Molecular Weight: 400.431
• Mol file: 86334-63-6.mol

Synonyms:(3S,4S)-3-(benzyloxycarboxamido)-1-(2,4-dimethoxybenzyl)-4-(hydroxymethyl)-2-azetidinone

Chemical Property of benzyl((2S,3S)-1-(2,4-dimethoxybenzyl)-2-(hydroxymethyl)-4-oxoazetidin-3-yl)carbamate

Chemical Property:

Purity/Quality:

98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl((2S,3S)-1-(2,4-dimethoxybenzyl)-2-(hydroxymethyl)-4-oxoazetidin-3-yl)carbamate

There total 11 articles about benzyl((2S,3S)-1-(2,4-dimethoxybenzyl)-2-(hydroxymethyl)-4-oxoazetidin-3-yl)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: 95.0%

(3S,4S)-3-(benzyloxycarboxamido)-1-(2,4-dimethoxybenzyl)-4-formyl-2-azetidinone (86299-41-4) → (3S,4S)-3-(benzyloxycarboxamido)-1-(2,4-dimethoxybenzyl)-4-(hydroxymethyl)-2-azetidinone (86334-63-6)

Guidance literature:

With methanol; sodium tetrahydroborate; In dichloromethane; at 0 ℃; for 2h;

Reference yield:

N-[(3S,4S)-cis-1-(2,4-dimethoxybenzyl)-4-formyl-2-oxo-3-azetidinyl]phthalimide (86299-39-0) + benzyl chloroformate (501-53-1,94274-21-2) → (3S,4S)-3-(benzyloxycarboxamido)-1-(2,4-dimethoxybenzyl)-4-(hydroxymethyl)-2-azetidinone (86334-63-6)

Guidance literature:

With sodium cyanoborohydride; sodium hydrogencarbonate; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; water; acetic acid;

Reference yield:

2,4-Dimethoxybenzylamine (20781-20-8) → (3S,4S)-3-(benzyloxycarboxamido)-1-(2,4-dimethoxybenzyl)-4-(hydroxymethyl)-2-azetidinone (86334-63-6)

Guidance literature:

Multi-step reaction with 7 steps

1: magnesium sulfate / dichloromethane / 2.33 h / 0 - 20 °C

2: triethylamine / dichloromethane / 16.5 h / 0 - 20 °C

3: hydrazine hydrate / ethanol / 3.33 h / Reflux

4: sodium hydrogencarbonate / ethyl acetate / 3 h / 0 - 20 °C

5: water; toluene-4-sulfonic acid / tetrahydrofuran / 16 h / 70 °C

6: sodium periodate / water; ethyl acetate / 2 h / 50 °C

7: methanol; sodium tetrahydroborate / dichloromethane / 2 h / 0 °C

With methanol; sodium tetrahydroborate; sodium periodate; water; sodium hydrogencarbonate; magnesium sulfate; toluene-4-sulfonic acid; hydrazine hydrate; triethylamine; In tetrahydrofuran; ethanol; dichloromethane; water; ethyl acetate;

upstream raw materials:

(3S,4S)-3-(benzyloxycarboxamido)-1-(2,4-dimethoxybenzyl)-4-formyl-2-azetidinone

N-[(3S,4S)-cis-1-(2,4-dimethoxybenzyl)-4-formyl-2-oxo-3-azetidinyl]phthalimide

benzyl chloroformate

(R,E)-1-(2,4-dimethoxyphenyl)-N-((2,2-dimethyl-1,3-dioxolan-4-yl)methylene)methanamine

Downstream raw materials:

(3S,4S)-3-benzyloxycarbonylamino-4-hydroxymethyl-2-azetidinone

Refernces

• 1、 -. "MONOBACTAM ORGANIC COMPOUNDS FOR THE TREATMENT OF BACTERIAL INFECTIONS". Paragraph 0411. . Retrieved 2015/11/10.
• 2、 Mastalerz, Harold,Menard, Marcel,Vinet, Vivianne,Desiderio, James,Fung-Tomc, Joan,et al.. "An Examination of O-2-Isocephems as Orally Absorbable Antibiotics". . p. 1190 - 1196. Retrieved 2007/10/02.