5-Hexenal, 2,4-bis(phenylmethoxy)-, (2R,4S)-

Base Information

• Chemical Name: 5-Hexenal, 2,4-bis(phenylmethoxy)-, (2R,4S)-
• CAS No.: 152838-13-6
• Molecular Formula: C20H22O3
• Molecular Weight: 310.393
• Mol file: 152838-13-6.mol

Synonyms:

Chemical Property of 5-Hexenal, 2,4-bis(phenylmethoxy)-, (2R,4S)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-Hexenal, 2,4-bis(phenylmethoxy)-, (2R,4S)-

There total 6 articles about 5-Hexenal, 2,4-bis(phenylmethoxy)-, (2R,4S)- 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: 86.0%

methyl 2,4-di-O-benzyl-3,6-dideoxy-6-iodo-α-D-ribo-hexopyranoside (152838-12-5) → (2R,4S)-dibenzyloxyhex-5-enal (152838-13-6)

Guidance literature:

With silver-graphite; zinc; In tetrahydrofuran; for 0.166667h; Ambient temperature;

DOI:10.1016/S0040-4020(01)96261-1

Reference yield:

methyl 4,6-O-benzylidene-2,3-anhydro-α-D-mannopyranoside (3150-16-1) → (2R,4S)-dibenzyloxyhex-5-enal (152838-13-6)

Guidance literature:

Multi-step reaction with 6 steps

1: 90 percent / LiAlH₄ / diethyl ether / 12 h / Heating

2: 1.) oxalyl chloride, DMSO, NEt₃, 2.) NaBH₄ / 1.) CH₂Cl₂, -70 deg C to room temperature, 2.) CH₂Cl₂, water, 2 h

3: 95 percent / 1.) KH / tetrahydrofuran / 0.5 h / Ambient temperature; 1.) 30 min 0 deg C to room temperature

4: 66 percent / BH₃*NMe₃/AlCl₃, molecular sieves 4Angstroem / toluene / 0.17 h / Ambient temperature

5: 88 percent / imidazole, PPh₃, iodine / toluene / 4 h / Ambient temperature

6: 86 percent / Zn/Ag-graphite / tetrahydrofuran / 0.17 h / Ambient temperature

With 1H-imidazole; sodium tetrahydroborate; silver-graphite; lithium aluminium tetrahydride; aluminium trichloride; oxalyl dichloride; trimethylamine-borane; 4 A molecular sieve; iodine; potassium hydride; dimethyl sulfoxide; triethylamine; triphenylphosphine; zinc; In tetrahydrofuran; diethyl ether; toluene;

DOI:10.1016/S0040-4020(01)96261-1

Reference yield:

methyl 4,6-O-benzylidene-3-deoxy-α-D-arabino-hexopyranoside (34266-73-4) → (2R,4S)-dibenzyloxyhex-5-enal (152838-13-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) oxalyl chloride, DMSO, NEt₃, 2.) NaBH₄ / 1.) CH₂Cl₂, -70 deg C to room temperature, 2.) CH₂Cl₂, water, 2 h

2: 95 percent / 1.) KH / tetrahydrofuran / 0.5 h / Ambient temperature; 1.) 30 min 0 deg C to room temperature

3: 66 percent / BH₃*NMe₃/AlCl₃, molecular sieves 4Angstroem / toluene / 0.17 h / Ambient temperature

4: 88 percent / imidazole, PPh₃, iodine / toluene / 4 h / Ambient temperature

5: 86 percent / Zn/Ag-graphite / tetrahydrofuran / 0.17 h / Ambient temperature

With 1H-imidazole; sodium tetrahydroborate; silver-graphite; aluminium trichloride; oxalyl dichloride; trimethylamine-borane; 4 A molecular sieve; iodine; potassium hydride; dimethyl sulfoxide; triethylamine; triphenylphosphine; zinc; In tetrahydrofuran; toluene;

DOI:10.1016/S0040-4020(01)96261-1

upstream raw materials:

methyl 2,4-di-O-benzyl-3,6-dideoxy-6-iodo-α-D-ribo-hexopyranoside

methyl 4,6-O-benzylidene-2,3-anhydro-α-D-mannopyranoside

methyl 4,6-O-benzylidene-3-deoxy-α-D-arabino-hexopyranoside

methyl 4,6-O-benzylidene-3-deoxy-ribo-hexopyranoside

Downstream raw materials:

(2R,4S)-dibenzyloxy-1,1-dimethoxy-hex-5-ene

(2R,4R)-dibenzyloxy-6-tert-butyldiphenylsilyloxy-hexanal

(2R,4R)-dibenzyloxy-6-tert-butyldiphenylsilyloxy-1,1-dimethoxy-hexane

methyl (2R,4R)-dibenzyloxy-6-tert-butyldiphenylsilyloxy-hexanoate