methyl 2,3,6-trideoxy-3-C-methyl-4-O-(4-nitrobenzoyl)-α-L-threo-hex-2-enopyranoside

Base Information

• Chemical Name: methyl 2,3,6-trideoxy-3-C-methyl-4-O-(4-nitrobenzoyl)-α-L-threo-hex-2-enopyranoside
• CAS No.: 263327-90-8
• Molecular Formula: C₁₅H₁₇NO₆
• Molecular Weight: 307.303
• Mol file: 263327-90-8.mol

Synonyms:methyl 2,3,6-trideoxy-3-C-methyl-4-O-(4-nitrobenzoyl)-α-L-threo-hex-2-enopyranoside

Chemical Property of methyl 2,3,6-trideoxy-3-C-methyl-4-O-(4-nitrobenzoyl)-α-L-threo-hex-2-enopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 2,3,6-trideoxy-3-C-methyl-4-O-(4-nitrobenzoyl)-α-L-threo-hex-2-enopyranoside

There total 6 articles about methyl 2,3,6-trideoxy-3-C-methyl-4-O-(4-nitrobenzoyl)-α-L-threo-hex-2-enopyranoside 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: 61.0%

Methyl-2,3,6-tridesoxy-3-C-methyl-α-L-erythro-hex-2-enopyranosid (100017-90-1) + 4-nitro-benzoic acid (62-23-7) → methyl 2,3,6-trideoxy-3-C-methyl-4-O-(4-nitrobenzoyl)-α-L-threo-hex-2-enopyranoside (263327-90-8)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 20 ℃; for 18h;

DOI:10.1016/S0008-6215(99)00259-1

Reference yield:

methyl 2,3-O-benzylidene-6-deoxy-α-L-mannopyranoside (61199-73-3) → methyl 2,3,6-trideoxy-3-C-methyl-4-O-(4-nitrobenzoyl)-α-L-threo-hex-2-enopyranoside (263327-90-8)

Guidance literature:

Multi-step reaction with 4 steps

2.1: DMAP / methanol

2.2: H⁺ / methanol

3.1: ion exchange resin

4.1: 61 percent / PPh₃; diethyl azodicarboxylate / tetrahydrofuran / 18 h / 20 °C

With dmap; ion exchange resin; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; methanol; 1.1: Methylation / 2.1: Acetylation / 2.2: Rearrangement / 3.1: Deacetylation / 4.1: Substitution;

DOI:10.1016/S0008-6215(99)00259-1

Reference yield:

1,5-anhydro-1,2,6-trideoxy-3-C-methyl-L-ribo-hex-1-enitol (70717-87-2,70774-09-3,78086-62-1,78086-63-2,131350-66-8) → methyl 2,3,6-trideoxy-3-C-methyl-4-O-(4-nitrobenzoyl)-α-L-threo-hex-2-enopyranoside (263327-90-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: DMAP / methanol

1.2: H⁺ / methanol

2.1: ion exchange resin

3.1: 61 percent / PPh₃; diethyl azodicarboxylate / tetrahydrofuran / 18 h / 20 °C

With dmap; ion exchange resin; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; methanol; 1.1: Acetylation / 1.2: Rearrangement / 2.1: Deacetylation / 3.1: Substitution;

DOI:10.1016/S0008-6215(99)00259-1

upstream raw materials:

Methyl-2,3,6-tridesoxy-3-C-methyl-α-L-erythro-hex-2-enopyranosid

4-nitro-benzoic acid

methyl 2,3-O-benzylidene-6-deoxy-α-L-mannopyranoside

(2S,3S)-3-hydroxy-2-methyl-2H-pyran-4(3H)-one

Downstream raw materials:

Methyl-4-O-benzoyl-3-(benzoylamino)-2,3,6-tridesoxy-3-C-methyl-α-L-lyxo-hexopyranosid