(3aS,4S,7aR)-hexahydro-4H-furo[2,3-b]pyran-4-yl (4-nitrophenyl) carbonate

Base Information

• Chemical Name: (3aS,4S,7aR)-hexahydro-4H-furo[2,3-b]pyran-4-yl (4-nitrophenyl) carbonate
• CAS No.: 1075209-47-0
• Molecular Formula: C₁₄H₁₅NO₇
• Molecular Weight: 309.276
• Mol file: 1075209-47-0.mol

Synonyms:(3aS,4S,7aR)-hexahydro-4H-furo[2,3-b]pyran-4-yl (4-nitrophenyl) carbonate

Chemical Property of (3aS,4S,7aR)-hexahydro-4H-furo[2,3-b]pyran-4-yl (4-nitrophenyl) carbonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3aS,4S,7aR)-hexahydro-4H-furo[2,3-b]pyran-4-yl (4-nitrophenyl) carbonate

There total 12 articles about (3aS,4S,7aR)-hexahydro-4H-furo[2,3-b]pyran-4-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: 99.0%

(3aS,4S,7aR)-hexahydro-2H-furo[2,3-b]pyran-4-ol (1075209-46-9) + 4-Nitrophenyl chloroformate (7693-46-1) → (3aS,4S,7aR)-hexahydro-4H-furo[2,3-b]pyran-4-yl (4-nitrophenyl) carbonate (1075209-47-0)

Guidance literature:

With pyridine; In dichloromethane; at 0 - 20 ℃; for 2h; Inert atmosphere;

DOI:10.1021/jm1012787

Reference yield:

(-)-(1S,5R)-2-oxabicyclo[3.3.0]oct-6-en-3-one (26054-46-6) → (3aS,4S,7aR)-hexahydro-4H-furo[2,3-b]pyran-4-yl (4-nitrophenyl) carbonate (1075209-47-0)

Guidance literature:

Multi-step reaction with 8 steps

1.1: lithium aluminium tetrahydride / diethyl ether / 1.5 h / 0 °C / Inert atmosphere

2.1: 2,4,6-trimethyl-pyridine / dichloromethane / 7 h / -78 °C / Inert atmosphere

3.1: 2,6-dimethylpyridine / dichloromethane / 0.17 h / -78 °C / Inert atmosphere

4.1: potassium carbonate / methanol / 2 h / 23 °C

5.1: ozone / dichloromethane / 0.08 h / -78 °C / Inert atmosphere

5.2: 2 h / 0 °C / Inert atmosphere

6.1: triethylsilane; boron trifluoride diethyl etherate / dichloromethane / 0.17 h / 0 °C / Inert atmosphere

7.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 23 °C

8.1: pyridine / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere

With pyridine; 2,6-dimethylpyridine; 2,4,6-trimethyl-pyridine; triethylsilane; lithium aluminium tetrahydride; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; potassium carbonate; ozone; In tetrahydrofuran; methanol; diethyl ether; dichloromethane;

DOI:10.1021/jm1012787

Reference yield:

(4S,4aS,7aR)-4-(tert-butyldimethylsilyloxy)hexahydrofuro-[2,3-b]pyrane (1262482-21-2) → (3aS,4S,7aR)-hexahydro-4H-furo[2,3-b]pyran-4-yl (4-nitrophenyl) carbonate (1075209-47-0)

Guidance literature:

Multi-step reaction with 2 steps

1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 23 °C

2: pyridine / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere

With pyridine; tetrabutyl ammonium fluoride; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jm1012787

upstream raw materials:

2R-(2-acetoxyethyl)-3-cyclopenten-1S-ol

(1S,2R)-2-[1-(tert-butyldimethylsilyloxy)cyclopent-3-en-2-yl]ethyl acetate

C₁₃H₂₆O₂Si

(4S,4aS,7aR)-4-(tert-butyldimethylsilyloxy)hexahydrofuro-[2,3-b]pyrane

Downstream raw materials:

(3aS,4S,7aR)-hexahydro-2H-furo[2,3-b]pyran-4-yl-(2S,3R)-3-hydroxy-4-(4-(hydroxymethyl)-N-isobutylphenylsulfonamido)-1-phenylbutan-2-yl carbamate

GRL-0476

(3aS,4S,7aR)-hexahydro-2H-furo[2,3-b]pyran-4-yl-(2S,3R)-4-(4-amino-N-isobutylphenylsulfonamido)-3-hydroxy-1-phenylbutan-2-yl carbamate