methyl 5-deoxy-5-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-2,3-O-(1-methylethylidene)pentofuranoside

Base Information

• Chemical Name: methyl 5-deoxy-5-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-2,3-O-(1-methylethylidene)pentofuranoside
• CAS No.: 14131-76-1
• Molecular Formula: C17H19 N O6
• Molecular Weight: 333.3359
• Mol file: 14131-76-1.mol

Synonyms:Ribofuranoside,methyl 5-deoxy-2,3-O-isopropylidene-5-phthalimido-, b-D- (8CI); NSC 145054

Chemical Property of methyl 5-deoxy-5-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-2,3-O-(1-methylethylidene)pentofuranoside

Chemical Property:

• Vapor Pressure: 3.28E-08mmHg at 25°C
• Boiling Point: 447.7°C at 760 mmHg
• Flash Point: 224.6°C
• Density: 1.38g/cm³

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of methyl 5-deoxy-5-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-2,3-O-(1-methylethylidene)pentofuranoside

There total 5 articles about methyl 5-deoxy-5-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-2,3-O-(1-methylethylidene)pentofuranoside 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: 96.0%

phthalimide (136918-14-4,85-41-6) + ((3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methanol (4099-85-8,828937-29-7) → 2-(((4R,6R)-6-methoxy-2,2-dimethyltetrahydrofuro [3,4-d][1,3]dioxol-4-yl)methyl)isoindoline-1,3-dione (14131-76-1)

Guidance literature:

phthalimide; With triphenylphosphine; In tetrahydrofuran; at 23 ℃; for 1h;

((3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methanol; With di-isopropyl azodicarboxylate; In tetrahydrofuran; at 0 - 23 ℃; for 5.5h;

DOI:10.1002/chem.201801756

Reference yield: 84.0%

potassium phtalimide (1074-82-4) + methyl 2,3-O-isopropylidene-5-O-p-tolylsulfonyl-β-D-ribofuranoside (4137-56-8) → 2-(((4R,6R)-6-methoxy-2,2-dimethyltetrahydrofuro [3,4-d][1,3]dioxol-4-yl)methyl)isoindoline-1,3-dione (14131-76-1)

Guidance literature:

With sodium iodide; In N,N-dimethyl-formamide; Heating;

Reference yield: 76.0%

3-hydroxy-2-(((4R,6R)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyl)isoindolin-1-one → 2-(((4R,6R)-6-methoxy-2,2-dimethyltetrahydrofuro [3,4-d][1,3]dioxol-4-yl)methyl)isoindoline-1,3-dione (14131-76-1)

Guidance literature:

With nickel(IV) oxide; In toluene; for 12h; Reagent/catalyst; Reflux; Inert atmosphere;

DOI:10.3390/molecules27020548

upstream raw materials:

1-O-methyl-2,3-O-isopropylidene-5-O-(methanesulfonyl)-β-D-ribofuranoside

potassium phtalimide

phthalimide

((3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methanol