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

Base Information

• Chemical Name: (3R,4R,5S,6R)-2-Acetoxy-5-acetylamino-4-benzyloxy-3-phenylselanyl-6-((1S,2R)-1,2,3-tris-benzyloxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester
• CAS No.: 116096-64-1
• Molecular Formula: C₄₈H₅₁NO₁₀Se
• Molecular Weight: 880.894
• Mol file: 116096-64-1.mol

Synonyms:

Chemical Property of (3R,4R,5S,6R)-2-Acetoxy-5-acetylamino-4-benzyloxy-3-phenylselanyl-6-((1S,2R)-1,2,3-tris-benzyloxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,4R,5S,6R)-2-Acetoxy-5-acetylamino-4-benzyloxy-3-phenylselanyl-6-((1S,2R)-1,2,3-tris-benzyloxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester

There total 10 articles about (3R,4R,5S,6R)-2-Acetoxy-5-acetylamino-4-benzyloxy-3-phenylselanyl-6-((1S,2R)-1,2,3-tris-benzyloxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester 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: 11.0%

Phenylselenyl chloride (5707-04-0) + methyl 5-acetamido-4,7,8,9-tetra-O-benzyl-2,3-dehydro-3,5-dideoxy-D-glycero-D-galacto-2-nonulopyranosonate (116096-63-0) → (3R,4R,5S,6R)-2-Acetoxy-5-acetylamino-4-benzyloxy-3-phenylselanyl-6-((1S,2R)-1,2,3-tris-benzyloxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester (116096-64-1) + (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-3,5-dideoxy-3-phenylseleno-D-erythro-β-L-gluco-2-nonulopyranosonate (125288-70-2,125288-71-3,128596-94-1)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; silver(I) acetate; In 1,2-dichloro-ethane; at 0 ℃; for 0.5h;

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

Reference yield: 11.0%

benzeneselenenyl acetate (104023-12-3) + methyl 5-acetamido-4,7,8,9-tetra-O-benzyl-2,3-dehydro-3,5-dideoxy-D-glycero-D-galacto-2-nonulopyranosonate (116096-63-0) → (3R,4R,5S,6R)-2-Acetoxy-5-acetylamino-4-benzyloxy-3-phenylselanyl-6-((1S,2R)-1,2,3-tris-benzyloxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester (116096-64-1) + (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-3,5-dideoxy-3-phenylseleno-D-erythro-β-L-gluco-2-nonulopyranosonate (125288-70-2,125288-71-3,128596-94-1)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In 1,2-dichloro-ethane; at 0 ℃; for 0.5h;

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

Reference yield:

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) → (3R,4R,5S,6R)-2-Acetoxy-5-acetylamino-4-benzyloxy-3-phenylselanyl-6-((1S,2R)-1,2,3-tris-benzyloxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester (116096-64-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 20 percent / n-Bu₃SnOTf, molecular sieves 4 A / CCl₄ / 16 h / Ambient temperature

2: 79 percent / trimethylsilyl triflate / 1,2-dichloro-ethane / 0.5 h / 0 °C

With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; tributylstannyl trifluoromethanesulfonate; In tetrachloromethane; 1,2-dichloro-ethane;

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

upstream raw materials:

Phenylselenyl chloride

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

benzeneselenenyl acetate

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