methyl 5-(o-nitrophenyl)seleno-3,4,5-trideoxy-β-D,L-glycerohex-3-enos-2-ulopyranoside ethylene acetal

Base Information

• Chemical Name: methyl 5-(o-nitrophenyl)seleno-3,4,5-trideoxy-β-D,L-glycerohex-3-enos-2-ulopyranoside ethylene acetal
• CAS No.: 141270-44-2
• Molecular Formula: C₁₅H₁₇NO₆Se
• Molecular Weight: 386.263
• Mol file: 141270-44-2.mol

Synonyms:

Chemical Property of methyl 5-(o-nitrophenyl)seleno-3,4,5-trideoxy-β-D,L-glycerohex-3-enos-2-ulopyranoside ethylene acetal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 5-(o-nitrophenyl)seleno-3,4,5-trideoxy-β-D,L-glycerohex-3-enos-2-ulopyranoside ethylene acetal

There total 21 articles about methyl 5-(o-nitrophenyl)seleno-3,4,5-trideoxy-β-D,L-glycerohex-3-enos-2-ulopyranoside ethylene acetal 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: 85.0%

ortho-nitrophenyl selenocyanate (51694-22-5) + methyl 3,4-dideoxy-α-D,L-glycerohex-3-enos-2-ulopyranoside ethylene acetal (126380-46-9,126380-47-0,141270-40-8,141270-41-9) → methyl 5-(o-nitrophenyl)seleno-3,4,5-trideoxy-β-D,L-glycerohex-3-enos-2-ulopyranoside ethylene acetal (126380-50-5,141270-44-2,141270-45-3)

Guidance literature:

With tributylphosphine; In tetrahydrofuran; for 1h;

DOI:10.1135/cccc19920159

Reference yield:

5-acetoxymethyl-2-furaldehyde (10551-58-3) → (3R,6S)-6-[1,3]Dioxolan-2-yl-6-methoxy-3-(2-nitro-phenylselanyl)-3,6-dihydro-2H-pyran (126380-50-5,141270-44-2,141270-45-3)

Guidance literature:

Multi-step reaction with 6 steps

2: MeONa / methanol

3: m-ClPBA

4: Ag₂O

5: LAH / diethyl ether / -78 °C

6: Bu₃P / tetrahydrofuran / Ambient temperature

With lithium aluminium tetrahydride; tributylphosphine; sodium methylate; 3-chloro-benzenecarboperoxoic acid; silver(l) oxide; In tetrahydrofuran; methanol; diethyl ether;

DOI:10.1016/S0040-4039(01)80669-9

Reference yield:

5-acetoxymethyl-2-furaldehyde (10551-58-3) → (3S,6S)-6-[1,3]Dioxolan-2-yl-6-methoxy-3-(2-nitro-phenylselanyl)-3,6-dihydro-2H-pyran (126380-50-5,141270-44-2,141270-45-3)

Guidance literature:

Multi-step reaction with 6 steps

2: MeONa / methanol

3: m-ClPBA

4: Ag₂O

5: LAH / diethyl ether / -78 °C

6: Bu₃P / tetrahydrofuran / Ambient temperature

With lithium aluminium tetrahydride; tributylphosphine; sodium methylate; 3-chloro-benzenecarboperoxoic acid; silver(l) oxide; In tetrahydrofuran; methanol; diethyl ether;

DOI:10.1016/S0040-4039(01)80669-9

upstream raw materials:

ortho-nitrophenyl selenocyanate

(3S,6S)-6-[1,3]Dioxolan-2-yl-6-methoxy-3,6-dihydro-2H-pyran-3-ol

5-acetoxymethyl-2-furaldehyde

[5-(1,3-dioxolan-2-yl)furan-2-yl]methanol