methyl 5-acetamido-4,7,8,9-tetra-O-benzyl-2,3,5-trideoxy-2-fluoro-3-phenylseleno-D-erythro-α-L-gluco-nonulopyranosate

Base Information

• Chemical Name: methyl 5-acetamido-4,7,8,9-tetra-O-benzyl-2,3,5-trideoxy-2-fluoro-3-phenylseleno-D-erythro-α-L-gluco-nonulopyranosate
• CAS No.: 116096-67-4
• Molecular Formula: C₄₆H₄₈FNO₈Se
• Molecular Weight: 840.847
• Mol file: 116096-67-4.mol

Synonyms:

Chemical Property of methyl 5-acetamido-4,7,8,9-tetra-O-benzyl-2,3,5-trideoxy-2-fluoro-3-phenylseleno-D-erythro-α-L-gluco-nonulopyranosate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 5-acetamido-4,7,8,9-tetra-O-benzyl-2,3,5-trideoxy-2-fluoro-3-phenylseleno-D-erythro-α-L-gluco-nonulopyranosate

There total 8 articles about methyl 5-acetamido-4,7,8,9-tetra-O-benzyl-2,3,5-trideoxy-2-fluoro-3-phenylseleno-D-erythro-α-L-gluco-nonulopyranosate 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: 88.0%

methyl 5-acetamido-4,7,8,9-tetra-O-benzyl-3,5-dideoxy-3-phenylseleno-D-erythro-β-L-gluco-2-nonulopyranosonate (125288-70-2,125288-71-3,128596-94-1) → methyl 5-acetamido-4,7,8,9-tetra-O-benzyl-2,3,5-trideoxy-2-fluoro-3-phenylseleno-D-erythro-α-L-gluco-nonulopyranosate (116096-67-4,116180-63-3,125356-39-0,125356-40-3,128658-86-6)

Guidance literature:

With diethylamino-sulfur trifluoride; In 1,2-dichloro-ethane; toluene; -40 deg C, 3h, then room temp., 1h;

DOI:10.1016/S0040-4020(01)97586-6

Reference yield:

Phenylselenyl chloride (5707-04-0) → methyl 5-acetamido-4,7,8,9-tetra-O-benzyl-2,3,5-trideoxy-2-fluoro-3-phenylseleno-D-erythro-α-L-gluco-nonulopyranosate (116096-67-4,116180-63-3,125356-39-0,125356-40-3,128658-86-6)

Guidance literature:

Multi-step reaction with 3 steps

2: 8 percent / trimethylsilyl triflate / 1,2-dichloro-ethane / 0.5 h / 0 °C

3: 88 percent / diethylaminosulfur trifluoride / toluene; 1,2-dichloro-ethane / 40 °C

With diethylamino-sulfur trifluoride; trimethylsilyl trifluoromethanesulfonate; In 1,2-dichloro-ethane; toluene;

DOI:10.1016/S0040-4039(00)61852-X

Reference yield:

5-acetamido-4,7,8,9-tetra-O-benzyl-2,3-dehydro-3,5-dideoxy-D-glycero-D-galacto-2-nonulopyranosonic acid (125288-69-9) → methyl 5-acetamido-4,7,8,9-tetra-O-benzyl-2,3,5-trideoxy-2-fluoro-3-phenylseleno-D-erythro-α-L-gluco-nonulopyranosate (116096-67-4,116180-63-3,125356-39-0,125356-40-3,128658-86-6)

Guidance literature:

Multi-step reaction with 3 steps

1: diethyl ether; methanol

2: 8 percent / trimethylsilyl triflate / 1,2-dichloro-ethane / 0.5 h / 0 °C

3: 88 percent / diethylaminosulfur trifluoride / toluene; 1,2-dichloro-ethane / 40 °C

With diethylamino-sulfur trifluoride; trimethylsilyl trifluoromethanesulfonate; In methanol; diethyl ether; 1,2-dichloro-ethane; toluene;

DOI:10.1016/S0040-4039(00)61852-X

upstream raw materials:

methyl 5-acetamido-4,7,8,9-tetra-O-benzyl-3,5-dideoxy-3-phenylseleno-D-erythro-β-L-gluco-2-nonulopyranosonate

Phenylselenyl chloride

2,3-dehydro-2-deoxy-N-acetylneuraminic acid

benzeneselenenyl acetate

Downstream raw materials:

C₁₀₀H₁₀₅NO₁₉Se

benzyl O--(2->3)-O-(2,6-di-O-benzyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside

methyl 5-acetamido-4,7,8,9-tetra-O-benzyl-2,3-dehydro-3,5-dideoxy-D-glycero-D-galacto-2-nonulopyranosonate

C₁₀₀H₁₀₅NO₁₉Se