2-(2',3';5'6-di-O-isopropylidene-α-D-mannofuranosyl)-α<(benzyloxycarbonyl)amino>-5-isoxazolidineacetic acid methylidene ester

Base Information

• Chemical Name: 2-(2',3';5'6-di-O-isopropylidene-α-D-mannofuranosyl)-α<(benzyloxycarbonyl)amino>-5-isoxazolidineacetic acid methylidene ester
• CAS No.: 105834-70-6
• Molecular Formula: C₂₆H₃₄N₂O₁₀
• Molecular Weight: 534.563
• Mol file: 105834-70-6.mol

Synonyms:

Chemical Property of 2-(2',3';5'6-di-O-isopropylidene-α-D-mannofuranosyl)-α<(benzyloxycarbonyl)amino>-5-isoxazolidineacetic acid methylidene ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-(2',3';5'6-di-O-isopropylidene-α-D-mannofuranosyl)-α<(benzyloxycarbonyl)amino>-5-isoxazolidineacetic acid methylidene ester

There total 4 articles about 2-(2',3';5'6-di-O-isopropylidene-α-D-mannofuranosyl)-α<(benzyloxycarbonyl)amino>-5-isoxazolidineacetic acid methylidene ester 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:

2,3;5,6-di-O-isopropylidene-D-mannose oxime (83258-84-8,99395-01-4,104012-86-4,136598-86-2) → 2-(2',3';5'6-di-O-isopropylidene-α-D-mannofuranosyl)-α<(benzyloxycarbonyl)amino>-5-isoxazolidineacetic acid methylidene ester (105834-70-6,105927-17-1)

Guidance literature:

Multi-step reaction with 2 steps

1: CHCl₃ / Heating

2: CHCl₃ / Heating

In chloroform;

DOI:10.1021/ja00235a044

Reference yield:

(S)-3-Benzyloxycarbonyl-5-oxo-4-vinyltetrahydro-1,3-oxazole (90292-75-4) + N-(2,3;5,6-di-O-isopropylidene-α-D-mannofuranosyl)nitrone (105834-65-9) → 2-(2',3';5'6-di-O-isopropylidene-α-D-mannofuranosyl)-α<(benzyloxycarbonyl)amino>-5-isoxazolidineacetic acid methylidene ester (105834-70-6,105927-17-1)

Guidance literature:

In chloroform; for 36h; Yield given; Heating;

DOI:10.1021/jo00252a035

Reference yield:

(S)-3-benzyloxycarbonyl-4-(2-methylthioethyl)oxazolidin-5-one (115481-99-7) → 2-(2',3';5'6-di-O-isopropylidene-α-D-mannofuranosyl)-α<(benzyloxycarbonyl)amino>-5-isoxazolidineacetic acid methylidene ester (105834-70-6,105927-17-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 96 percent / sodium metaperiodate / methanol; H₂O / 5 h

2: 65 percent / triethyl phosphite / xylene / 48 h / Heating

3: CHCl₃ / 36 h / Heating

With sodium periodate; triethyl phosphite; In methanol; chloroform; water; xylene;

DOI:10.1021/jo00252a035

upstream raw materials:

(S)-3-Benzyloxycarbonyl-5-oxo-4-vinyltetrahydro-1,3-oxazole

N-(2,3;5,6-di-O-isopropylidene-α-D-mannofuranosyl)nitrone

2,3;5,6-di-O-isopropylidene-D-mannose oxime

(S)-3-benzyloxycarbonyl-4-(2-methylthioethyl)oxazolidin-5-one

Downstream raw materials:

(αS,5S)-α-<(benzyloxycarbonyl)amino>-5-isoxazolidineacetic acid methylidene ester

(αS,5R)-α-<(benzyloxycarbonyl)amino>-5-isoxazolidineacetic acid methylidene ester

(αS,5S)-α-<(benzyloxycarbonyl)amino>-4,5-dihydro-5-isoxazoleacetic acid methylidene ester

(αS,5S)-α-<(benzyloxycarbonyl)amino>-4,5-dihydro-5-isoxazoleacetic acid methylidene ester