methyl 5-acetamido-4,7,8,9-tetra-O-benzyl-2,3,5-trideoxy-2-fluoro-3-(phenylseleno)-D-erythro-β-L-manno-2-nonulopyranosonate

Base Information

• Chemical Name: methyl 5-acetamido-4,7,8,9-tetra-O-benzyl-2,3,5-trideoxy-2-fluoro-3-(phenylseleno)-D-erythro-β-L-manno-2-nonulopyranosonate
• CAS No.: 116180-63-3
• Molecular Formula: C₄₆H₄₈FNO₈Se
• Molecular Weight: 840.847
• Mol file: 116180-63-3.mol

Synonyms:methyl 5-acetamido-4,7,8,9-tetra-O-benzyl-2,3,5-trideoxy-2-fluoro-3-(phenylseleno)-D-erythro-β-L-manno-2-nonulopyranosonate

Chemical Property of methyl 5-acetamido-4,7,8,9-tetra-O-benzyl-2,3,5-trideoxy-2-fluoro-3-(phenylseleno)-D-erythro-β-L-manno-2-nonulopyranosonate

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-β-L-manno-2-nonulopyranosonate

There total 19 articles about methyl 5-acetamido-4,7,8,9-tetra-O-benzyl-2,3,5-trideoxy-2-fluoro-3-(phenylseleno)-D-erythro-β-L-manno-2-nonulopyranosonate 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: 70.0%

(3R,4R,5S,6R)-5-Acetylamino-4-benzyloxy-2-hydroxy-3-phenylselanyl-6-((1S,2R)-1,2,3-tris-benzyloxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester (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-β-L-manno-2-nonulopyranosonate (116180-63-3)

Guidance literature:

With diethylamino-sulfur trifluoride; In tetrahydrofuran; at -20 ℃; for 0.5h;

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

Reference yield:

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-β-L-manno-2-nonulopyranosonate (116180-63-3)

Guidance literature:

Multi-step reaction with 4 steps

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

2: 20 percent / n-Bu₃SnOTf, molecular sieves 4 A / CCl₄ / 16 h / Ambient temperature

3: 11 percent / trimethylsilyl triflate / 1,2-dichloro-ethane / 0.5 h / 0 °C

4: 70 percent / diethylaminosulfur trifluoride / tetrahydrofuran / -20 °C

With diethylamino-sulfur trifluoride; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; tributylstannyl trifluoromethanesulfonate; In tetrahydrofuran; tetrachloromethane; 1,2-dichloro-ethane; toluene;

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

upstream raw materials:

(3R,4R,5S,6R)-5-Acetylamino-4-benzyloxy-2-hydroxy-3-phenylselanyl-6-((1S,2R)-1,2,3-tris-benzyloxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester

Phenylselenyl chloride

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

methyl 2,3,4-tri-O-benzyl-D-glucopyranoside

Downstream raw materials:

(2R,3R,4R,5S,6R)-5-Acetylamino-4-benzyloxy-3-phenylselanyl-2-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-ylmethoxy)-6-((1S,2R)-1,2,3-tris-benzyloxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester

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