(1S,4R,5R)-4-(2-Nitro-phenylselanyl)-6,8-dioxa-bicyclo[3.2.1]oct-2-ene

Base Information

• Chemical Name: (1S,4R,5R)-4-(2-Nitro-phenylselanyl)-6,8-dioxa-bicyclo[3.2.1]oct-2-ene
• CAS No.: 454475-37-7
• Molecular Formula: C₁₂H₁₁NO₄Se
• Molecular Weight: 312.184
• Mol file: 454475-37-7.mol

Synonyms:(1S,4R,5R)-4-(2-Nitro-phenylselanyl)-6,8-dioxa-bicyclo[3.2.1]oct-2-ene

Chemical Property of (1S,4R,5R)-4-(2-Nitro-phenylselanyl)-6,8-dioxa-bicyclo[3.2.1]oct-2-ene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,4R,5R)-4-(2-Nitro-phenylselanyl)-6,8-dioxa-bicyclo[3.2.1]oct-2-ene

There total 2 articles about (1S,4R,5R)-4-(2-Nitro-phenylselanyl)-6,8-dioxa-bicyclo[3.2.1]oct-2-ene 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: 94.0%

ortho-nitrophenyl selenocyanate (51694-22-5) + 1,6-anhydro-3,4-dideoxy-β-D-threo-hex-3-enopyranose (50705-28-7) → (1S,4R,5R)-4-(2-Nitro-phenylselanyl)-6,8-dioxa-bicyclo[3.2.1]oct-2-ene (454475-37-7)

Guidance literature:

With tributylphosphine; In tetrahydrofuran; at 20 ℃; for 0.5h;

DOI:10.1081/CAR-120003745

Reference yield:

levoglucosenone (37112-31-5) → (1S,4R,5R)-4-(2-Nitro-phenylselanyl)-6,8-dioxa-bicyclo[3.2.1]oct-2-ene (454475-37-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / L-Selectride / tetrahydrofuran / -78 °C

2: 94 percent / n-Bu₃P / tetrahydrofuran / 0.5 h / 20 °C

With tributylphosphine; L-Selectride; In tetrahydrofuran;

DOI:10.1081/CAR-120003745

Reference yield: 89.0%

(1S,4R,5R)-4-(2-Nitro-phenylselanyl)-6,8-dioxa-bicyclo[3.2.1]oct-2-ene (454475-37-7) → 1,6-anhydro-2,3-dideoxy-β-D-erythro-hex-2-enopyranose (58394-31-3,52630-80-5,52630-81-6)

Guidance literature:

With pyridine; dihydrogen peroxide; at -20 - 20 ℃; for 4h;

DOI:10.1081/CAR-120003745

upstream raw materials:

ortho-nitrophenyl selenocyanate

1,6-anhydro-3,4-dideoxy-β-D-threo-hex-3-enopyranose

levoglucosenone

Downstream raw materials:

1,6-anhydro-2,3-dideoxy-β-D-erythro-hex-2-enopyranose

isolevoglucosenone