(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl 4-nitrophenyl carbonate

Base Information

• Chemical Name: (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl 4-nitrophenyl carbonate
• CAS No.: 192725-55-6
• Molecular Formula: C13H13NO7
• Molecular Weight: 295.249
• Mol file: 192725-55-6.mol

Synonyms:Carbonic acid (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl 4-nitrophenyl ester;

Chemical Property of (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl 4-nitrophenyl carbonate

Chemical Property:

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl 4-nitrophenyl carbonate

There total 20 articles about (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl 4-nitrophenyl 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: 92.0%

4-Nitrophenyl chloroformate (7693-46-1) + (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol (156928-09-5) → (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl-(4-nitrophenyl)carbonic acid (192725-55-6,252873-01-1,252873-35-1)

Guidance literature:

With pyridine; In dichloromethane; at 0 - 23 ℃; for 12h; Inert atmosphere;

DOI:10.1021/acs.joc.0c02396

Reference yield: 55.0%

bis-(p-nitrophenyl) carbonate (5070-13-3) + (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol (156928-09-5) → (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl-(4-nitrophenyl)carbonic acid (192725-55-6,252873-01-1,252873-35-1)

Guidance literature:

With triethylamine; In dichloromethane; at 20 - 25 ℃;

Reference yield:

bis-(p-nitrophenyl) carbonate (5070-13-3) + (3SR,3aRS,6aSR)-3-hydroxy-4H-hexahydrofuro<2,3-b>furan → (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl-(4-nitrophenyl)carbonic acid (192725-55-6,252873-01-1,252873-35-1)

Guidance literature:

(3SR,3aRS,6aSR)-3-hydroxy-4H-hexahydrofuro<2,3-b>furan; With acetic anhydride; In 1,2-dimethoxyethane; Inert atmosphere; Resolution of racemate; Large scale;

bis-(p-nitrophenyl) carbonate; With triethylamine; In dichloromethane; at 20 - 25 ℃; for 48h; Time; stereoselective reaction; Inert atmosphere; Large scale;

DOI:10.1021/op700160a

upstream raw materials:

4-Nitrophenyl chloroformate

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

bis-(p-nitrophenyl) carbonate

3-acetoxy-(3R,3αS,6αR)-bis-tetrahydrofuran

Downstream raw materials:

((1S,2R)-1-Benzyl-3-cyclohexyloxyamino-2-hydroxy-propyl)-carbamic acid (3R,3aS,6aR)-(hexahydro-furo[2,3-b]furan-3-yl) ester

(3R,3AS,6AR)-hexahydrofuro[2,3-b]furan-3-yl (1S,2R)-3-[(1,3-benzodioxol-5-ylsulfonyl)(isobutyl)amino]-1-[4-(benzyloxy)benzyl]-2-hydroxypropylcarbamate

darunavir

C₂₇H₃₇N₃O₆S

Refernces

• 1、 -. "PROCESS FOR THE PREPARATION OF SULFONAMIDES USEFUL AS RETROVIRAL PROTEASE INHIBITORS". Page/Page column 34. . Retrieved 2013/03/26.
• 2、 -. "PROCESS FOR PREPARATION OF HIV PROTEASE INHIBITORS". Page/Page column 30-31. . Retrieved 2008/06/13.