2,5-Dioxopyrrolidin-1-yl ((3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl) carbonate

Base Information

• Chemical Name: 2,5-Dioxopyrrolidin-1-yl ((3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl) carbonate
• CAS No.: 253265-97-3
• Molecular Formula: C11H13 N O7
• Molecular Weight: 271.227
• European Community (EC) Number: 813-811-7
• UNII: 14EY0QM9CE
• DSSTox Substance ID: DTXSID201021089
• Nikkaji Number: J2.119.694K
• Wikidata: Q76416764
• Mol file: 253265-97-3.mol

Synonyms:253265-97-3;2,5-Dioxopyrrolidin-1-yl ((3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl) carbonate;[(3R,3aS,6aR)-Hydroxyhexahydrofuro[2,3-b]furanyl Succinimidyl Carbonate;14EY0QM9CE;[(3aS,4R,6aR)-2,3,3a,4,5,6a-hexahydrofuro[2,3-b]furan-4-yl] (2,5-dioxopyrrolidin-1-yl) carbonate;[(3R,3aS,6aR)-Hydroxyhexahydrofuro[2,3-|A]furanyl Succinimidyl Carbonate;[(3R,3aS,6aR)-Hexahydrofuro[2,3-b]furan-3-yl] (2,5-Dioxopyrrolidin-1-yl) Carbonate;2,5-Dioxopyrrolidin-1-yl ((3R,3aS,6aR)-hexahydrofuro(2,3-b)furan-3-yl) carbonate;Carbonic acid, 2,5-dioxo-1-pyrrolidinyl ((3R,3aS,6aR)-hexahydrofuro(2,3-b)furan-3-yl) ester;Carbonic acid, 2,5-dioxo-1-pyrrolidinyl [(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl] ester;UNII-14EY0QM9CE;SCHEMBL829342;1-({[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl}oxy)pyrrolidine-2,5-dione;DTXSID201021089;BCP09451;MFCD12031467;[(3R,3aS,6aR)-Hydroxyhexahydrofuro[2,3-?]furanyl Succinimidyl Carbonate;AKOS022184891;DS-3968;Carbonic Acid 2,5-Dioxo-1-pyrrolidinyl [(3R,3aS,6aR)-Hexahydrofuro[2,3-b]furan-3-yl] Ester;AC-26987;CS-0021268;F12132;A877624;A1-24388;J-502688;1-([[(3R,3aS,6aR)hexahydrofuro[2,3-b]furan-3-yloxy]-carbonyl]oxy)-2,5-pyrrolidinedione;1-([[(3R,3aS,6aR)hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy)-2,5-pyrrolidinedione;2,5-Dioxopyrrolidin-1-yl((3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl)carbonate;Carbonic acid (3R,3abeta,6abeta)-hexahydrofuro[2,3-b]furan-3alpha-yl 2,5-dioxopyrrolizino;Carbonic acid 2,5-dioxo-1-pyrrolidinyl [(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl] ester;2,5-Pyrrolidinedione,1-[[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl]oxy]carbonyl]oxy]- (9CI);1-[[[[(3R,3aS,6aR)-Hexahydrofuro[2,3-b]furan-3-yl]oxy]carbonyl]oxy]-5-pyrrolidinedione

Chemical Property of 2,5-Dioxopyrrolidin-1-yl ((3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl) carbonate

Chemical Property:

• Vapor Pressure: 2.41E-06mmHg at 25°C
• Melting Point: 122-125℃
• Refractive Index: 1.562
• Boiling Point: 391.8 °C at 760 mmHg
• Flash Point: 190.7 °C
• PSA: 91.37000
• Density: 1.51 g/cm³
• LogP: -0.09710
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly)
• XLogP3: -0.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 4
• Exact Mass: 271.06920175
• Heavy Atom Count: 19
• Complexity: 407

Purity/Quality:

99%min ^*data from raw suppliers

[(3R,3aS,6aR)-Hydroxyhexahydrofuro[2,3-b]furanylSuccinimidylCarbonate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1COC2C1C(CO2)OC(=O)ON3C(=O)CCC3=O
• Isomeric SMILES: C1CO[C@H]2[C@@H]1[C@H](CO2)OC(=O)ON3C(=O)CCC3=O

Technology Process of 2,5-Dioxopyrrolidin-1-yl ((3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl) carbonate

There total 35 articles about 2,5-Dioxopyrrolidin-1-yl ((3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl) carbonate 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: 99.6%

1-hydroxy-pyrrolidine-2,5-dione (6066-82-6) + C7H9ClO4 → 1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione (253265-97-3)

Guidance literature:

With triethylamine; In tetrahydrofuran; for 2h; Reflux;

Reference yield: 90.0%

di(succinimido) carbonate (74124-79-1) + (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol (156928-09-5) → 1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione (253265-97-3)

Guidance literature:

With pyridine; In tert-butyl methyl ether; at 25 - 40 ℃; for 62h; Solvent;

Reference yield:

di(succinimido) carbonate (74124-79-1) + (3S,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol → 1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione (253265-97-3)

Guidance literature:

With triethylamine; In acetonitrile; at 24 - 45 ℃; for 1h;

upstream raw materials:

di(succinimido) carbonate

(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol

γ-benzyloxymethyl-α,β-butenolide

(5S)-5-(hydroxymethyl)-5H-furan-2-one

Downstream raw materials:

Allyl-{(2R,3S)-3-[(3R,3aS,6aR)-(hexahydro-furo[2,3-b]furan-3-yl)oxycarbonylamino]-2-hydroxy-4-phenyl-butyl}-carbamic acid dec-9-enyl ester

But-3-enyl-{(2R,3S)-3-[(3R,3aS,6aR)-(hexahydro-furo[2,3-b]furan-3-yl)oxycarbonylamino]-2-hydroxy-4-phenyl-butyl}-carbamic acid 1-phenyl-dec-9-enyl ester

darunavir

{(1S,2R)-1-Benzyl-2-hydroxy-3-[isobutyl-(4-methoxy-benzenesulfonyl)-amino]-propyl}-carbamic acid (3R,3aS,6aR)-(hexahydro-furo[2,3-b]furan-3-yl) ester

Refernces

• 1、 -. "Industrial production method of high-purity Derenavir intermediate". Page/Page column 4-6. . Retrieved 2019/05/04.
• 2、 -. "METHOD FOR PRODUCING HEXAHYDROFUROFURANOL DERIVATIVE". Paragraph 0016; 0017; 0023; 0024. . Retrieved 2018/09/11.