2'-phenyl-(methyl 3,4-dideoxy-2-O-α-ethoxyethyl-4-C-methyl-α-L-arabinopyranosido)-<3,4:4,4',5'>-Δ^2'-oxazoline

Base Information

• Chemical Name: 2'-phenyl-(methyl 3,4-dideoxy-2-O-α-ethoxyethyl-4-C-methyl-α-L-arabinopyranosido)-<3,4:4,4',5'>-Δ^2'-oxazoline
• CAS No.: 92562-73-7
• Molecular Formula: C₁₈H₂₅NO₅
• Molecular Weight: 335.4

Synonyms:2'-phenyl-(methyl 3,4-dideoxy-2-O-α-ethoxyethyl-4-C-methyl-α-L-arabinopyranosido)-<3,4:4,4',5'>-Δ^2'-oxazoline

Chemical Property of 2'-phenyl-(methyl 3,4-dideoxy-2-O-α-ethoxyethyl-4-C-methyl-α-L-arabinopyranosido)-<3,4:4,4',5'>-Δ^2'-oxazoline

Chemical Property:

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Technology Process of 2'-phenyl-(methyl 3,4-dideoxy-2-O-α-ethoxyethyl-4-C-methyl-α-L-arabinopyranosido)-<3,4:4,4',5'>-Δ^2'-oxazoline

There total 4 articles about 2'-phenyl-(methyl 3,4-dideoxy-2-O-α-ethoxyethyl-4-C-methyl-α-L-arabinopyranosido)-<3,4:4,4',5'>-Δ^2'-oxazoline 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: 83.0%

2'-phenyl-(methyl 3,4-dideoxy-2-O-α-ethoxyethyl-4-C-iodomethyl-α-L-arabinopyranosido)-<3,4:4',5'>-Δ2'-oxazoline (92562-72-6) → 2'-phenyl-(methyl 3,4-dideoxy-2-O-α-ethoxyethyl-4-C-methyl-α-L-arabinopyranosido)-<3,4:4,4',5'>-Δ2'-oxazoline (92562-73-7)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In benzene; for 4h; Heating;

DOI:10.1139/v84-261

Reference yield:

Methyl-2,3-anhydro-β-D-erythro-pentopyranosid-4-ulose (55533-72-7) → 2'-phenyl-(methyl 3,4-dideoxy-2-O-α-ethoxyethyl-4-C-methyl-α-L-arabinopyranosido)-<3,4:4,4',5'>-Δ2'-oxazoline (92562-73-7)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) n-butyllithium / 1.) DME, hexane, 30 min; 2.) DME, 5 min

2: 1.) ammonia / 1.) ethanol, ice bath; 2.) 80 deg C, 30 min

3: 83 percent / sodium bicarbonate / CHCl₃ / 1 h / Ambient temperature

4: 0.077 g / iodonium dicollidine perchlorate / CHCl₃ / 4 h / Ambient temperature

5: 83 percent / tri-n-butyltin hydride, AIBN / benzene / 4 h / Heating

With n-butyllithium; 2,2'-azobis(isobutyronitrile); iodonium di(2,4,6-trimethylpyridine) perchlorate; ammonia; tri-n-butyl-tin hydride; sodium hydrogencarbonate; In chloroform; benzene;

DOI:10.1139/v84-261

Reference yield:

methyl 2,3-anhydro-4-C-methylene-β-D-erythro-pentopyranoside (74872-27-8) → 2'-phenyl-(methyl 3,4-dideoxy-2-O-α-ethoxyethyl-4-C-methyl-α-L-arabinopyranosido)-<3,4:4,4',5'>-Δ2'-oxazoline (92562-73-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) ammonia / 1.) ethanol, ice bath; 2.) 80 deg C, 30 min

2: 83 percent / sodium bicarbonate / CHCl₃ / 1 h / Ambient temperature

3: 0.077 g / iodonium dicollidine perchlorate / CHCl₃ / 4 h / Ambient temperature

4: 83 percent / tri-n-butyltin hydride, AIBN / benzene / 4 h / Heating

With 2,2'-azobis(isobutyronitrile); iodonium di(2,4,6-trimethylpyridine) perchlorate; ammonia; tri-n-butyl-tin hydride; sodium hydrogencarbonate; In chloroform; benzene;

DOI:10.1139/v84-261

upstream raw materials:

2'-phenyl-(methyl 3,4-dideoxy-2-O-α-ethoxyethyl-4-C-iodomethyl-α-L-arabinopyranosido)-<3,4:4',5'>-Δ^2'-oxazoline

Methyl-2,3-anhydro-β-D-erythro-pentopyranosid-4-ulose

methyl 2,3-anhydro-4-C-methylene-β-D-erythro-pentopyranoside

methyl 3-amino-3,4-dideoxy-4-C-methylene-α-L-threo-pentapyranoside

Downstream raw materials:

3'-N-methyl-2'-phenyl-(methyl 3,4-dideoxy-4-C-methyl-α-L-arabinopyranosido)-<3,4:4',5'>-oxazolidine

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