ethyl 2-O-acetyl-3-O-benzyl-4-(2,4-O-benzylidene-3-deoxy-L-glycero-tetronamido)-4,6-dideoxy-1-thio-α-D-mannopyranoside

Base Information

• Chemical Name: ethyl 2-O-acetyl-3-O-benzyl-4-(2,4-O-benzylidene-3-deoxy-L-glycero-tetronamido)-4,6-dideoxy-1-thio-α-D-mannopyranoside
• CAS No.: 566934-67-6
• Molecular Formula: C₂₈H₃₅NO₇S
• Molecular Weight: 529.654
• Mol file: 566934-67-6.mol

Synonyms:ethyl 2-O-acetyl-3-O-benzyl-4-(2,4-O-benzylidene-3-deoxy-L-glycero-tetronamido)-4,6-dideoxy-1-thio-α-D-mannopyranoside

Chemical Property of ethyl 2-O-acetyl-3-O-benzyl-4-(2,4-O-benzylidene-3-deoxy-L-glycero-tetronamido)-4,6-dideoxy-1-thio-α-D-mannopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl 2-O-acetyl-3-O-benzyl-4-(2,4-O-benzylidene-3-deoxy-L-glycero-tetronamido)-4,6-dideoxy-1-thio-α-D-mannopyranoside

There total 3 articles about ethyl 2-O-acetyl-3-O-benzyl-4-(2,4-O-benzylidene-3-deoxy-L-glycero-tetronamido)-4,6-dideoxy-1-thio-α-D-mannopyranoside 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: 97.0%

2,4-O-benzylidene-3-deoxy-L-glycero-tetronic acid (566934-90-5) + ethyl 4-amino-2-O-acetyl-3-O-benzyl-4,6-dideoxy-1-thio-α-D-mannopyranoside (566934-66-5) → ethyl 2-O-acetyl-3-O-benzyl-4-(2,4-O-benzylidene-3-deoxy-L-glycero-tetronamido)-4,6-dideoxy-1-thio-α-D-mannopyranoside (566934-67-6)

Guidance literature:

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20 ℃; for 1h;

DOI:10.1039/b211660j

Reference yield:

(3R)-1,3-O-benzylidine-1,3,4-butanetriol (566934-88-1) → ethyl 2-O-acetyl-3-O-benzyl-4-(2,4-O-benzylidene-3-deoxy-L-glycero-tetronamido)-4,6-dideoxy-1-thio-α-D-mannopyranoside (566934-67-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 85 percent / pyridinium dichromate / dimethylformamide / 20 °C

2: 97 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride; HOBT / CH₂Cl₂ / 1 h / 20 °C

With dipyridinium dichromate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1039/b211660j

Reference yield:

ethyl 2-O-acetyl-4-azido-3-O-benzyl-4,6-dideoxy-1-thio-α-D-mannopyranoside (115234-11-2) → ethyl 2-O-acetyl-3-O-benzyl-4-(2,4-O-benzylidene-3-deoxy-L-glycero-tetronamido)-4,6-dideoxy-1-thio-α-D-mannopyranoside (566934-67-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 95 percent / H₂S / pyridine; H₂O / 3 h / 40 °C

2: 97 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride; HOBT / CH₂Cl₂ / 1 h / 20 °C

With hydrogen sulfide; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In pyridine; dichloromethane; water;

DOI:10.1039/b211660j

upstream raw materials:

2,4-O-benzylidene-3-deoxy-L-glycero-tetronic acid

ethyl 4-amino-2-O-acetyl-3-O-benzyl-4,6-dideoxy-1-thio-α-D-mannopyranoside

(3R)-1,3-O-benzylidine-1,3,4-butanetriol

ethyl 2-O-acetyl-4-azido-3-O-benzyl-4,6-dideoxy-1-thio-α-D-mannopyranoside

Downstream raw materials:

5-methoxycarbonylpentyl 3-O-benzyl-4-(2,4-O-benzylidene-3-deoxy-L-glycero-tetronamido)-4,6-dideoxy-α-D-mannopyranosyl-(1->2)-3-O-benzyl-4-(2,4-O-benzylidene-3-deoxy-L-glycero-tetronamido)-4,6-dideoxy-α-D-mannopyranoside

5-methoxycarbonylpentyl 2-O-acetyl-3-O-benzyl-4-(2,4-O-benzylidene-3-deoxy-L-glycero-tetronamido)-4,6-dideoxy-α-D-mannopyranosyl-(1->2)-3-O-benzyl-4-(2,4-O-benzylidene-3-deoxy-L-glycero-tetronamido)-4,6-dideoxy-α-D-mannopyranoside