methyl 5,7,8,9-tetra-O-acetyl-2,5-anhydro-4-benzoylamino-3,4-dideoxy-D-glycero-D-talo-non-2-enonate

Base Information

• Chemical Name: methyl 5,7,8,9-tetra-O-acetyl-2,5-anhydro-4-benzoylamino-3,4-dideoxy-D-glycero-D-talo-non-2-enonate
• CAS No.: 189143-88-2
• Molecular Formula: C₂₅H₂₉NO₁₂
• Molecular Weight: 535.505

Synonyms:methyl 5,7,8,9-tetra-O-acetyl-2,5-anhydro-4-benzoylamino-3,4-dideoxy-D-glycero-D-talo-non-2-enonate

Chemical Property of methyl 5,7,8,9-tetra-O-acetyl-2,5-anhydro-4-benzoylamino-3,4-dideoxy-D-glycero-D-talo-non-2-enonate

Chemical Property:

Purity/Quality:

98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 5,7,8,9-tetra-O-acetyl-2,5-anhydro-4-benzoylamino-3,4-dideoxy-D-glycero-D-talo-non-2-enonate

There total 2 articles about methyl 5,7,8,9-tetra-O-acetyl-2,5-anhydro-4-benzoylamino-3,4-dideoxy-D-glycero-D-talo-non-2-enonate 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: 48.0%

methyl (2,4,5,7,8,9-hexa-O-acetyl-3-deoxy-D-glycero-β-D-galacto-2-nonulopyranosid)onate (123843-50-5) + benzonitrile (100-47-0) → methyl 5,7,8,9-tetra-O-acetyl-2,6-anhydro-4-benzoylamino-3,4-dideoxy-D-glycero-D-galacto-non-2-enonate (173467-22-6) + methyl 5,7,8,9-tetra-O-acetyl-2,5-anhydro-4-benzoylamino-3,4-dideoxy-D-glycero-D-talo-non-2-enonate (189143-88-2)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; for 5h; Ambient temperature;

DOI:10.1016/S0008-6215(96)00302-3

Reference yield:

methyl 4,5,7,8,9-penta-O-acetyl-2,6-anhydro-2-chloro-2,3-dideoxy-D-glycero-D-galacto-2-nonulopyranosonate (139110-77-3) → methyl 5,7,8,9-tetra-O-acetyl-2,5-anhydro-4-benzoylamino-3,4-dideoxy-D-glycero-D-talo-non-2-enonate (189143-88-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 97 percent / pyridine / 1 h / 50 °C

2: Me₃SiOTf / 3 h / 20 °C

With trimethylsilyl trifluoromethanesulfonate; In pyridine; 1: Elimination / 2: Ritter reaction;

DOI:10.1016/S0008-6215(99)00236-0

Reference yield: 82.0%

methyl 5,7,8,9-tetra-O-acetyl-2,5-anhydro-4-benzoylamino-3,4-dideoxy-D-glycero-D-talo-non-2-enonate (189143-88-2) → (1S,5S,7R,8R,9R)-8-Acetoxy-9-bromo-3-phenyl-7-((1R,2R)-1,2,3-triacetoxy-propyl)-4,6-dioxa-2-aza-bicyclo[3.3.1]non-2-ene-5-carboxylic acid methyl ester

Guidance literature:

With N-Bromosuccinimide; In methanol; for 2h; Ambient temperature;

DOI:10.1016/S0008-6215(96)00302-3

upstream raw materials:

methyl (2,4,5,7,8,9-hexa-O-acetyl-3-deoxy-D-glycero-β-D-galacto-2-nonulopyranosid)onate

benzonitrile

methyl 4,5,7,8,9-penta-O-acetyl-2,6-anhydro-2-chloro-2,3-dideoxy-D-glycero-D-galacto-2-nonulopyranosonate

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