methyl 5-acetamido-2,6-anhydro-4-O-benzoyl-3,5-dideoxy-8,9-O-isopropylidene-D-glycero-D-galacto-non-2-enoate

Base Information

• Chemical Name: methyl 5-acetamido-2,6-anhydro-4-O-benzoyl-3,5-dideoxy-8,9-O-isopropylidene-D-glycero-D-galacto-non-2-enoate
• CAS No.: 134699-92-6
• Molecular Formula: C₂₂H₂₇NO₉
• Molecular Weight: 449.458
• Mol file: 134699-92-6.mol

Synonyms:methyl 5-acetamido-2,6-anhydro-4-O-benzoyl-3,5-dideoxy-8,9-O-isopropylidene-D-glycero-D-galacto-non-2-enoate

Chemical Property of methyl 5-acetamido-2,6-anhydro-4-O-benzoyl-3,5-dideoxy-8,9-O-isopropylidene-D-glycero-D-galacto-non-2-enoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 5-acetamido-2,6-anhydro-4-O-benzoyl-3,5-dideoxy-8,9-O-isopropylidene-D-glycero-D-galacto-non-2-enoate

There total 5 articles about methyl 5-acetamido-2,6-anhydro-4-O-benzoyl-3,5-dideoxy-8,9-O-isopropylidene-D-glycero-D-galacto-non-2-enoate 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: 90.0%

benzoyl chloride (98-88-4) + Methyl 5-acetamido-2,3,5-trideoxy-8,9-O-isopropylidene-D-glycero-D-galacto-non-2-enopyranosonate (108999-10-6) → methyl 5-acetamido-2,6-anhydro-4-O-benzoyl-3,5-dideoxy-8,9-O-isopropylidene-D-glycero-D-galacto-non-2-enoate (134699-92-6)

Guidance literature:

With pyridine; In dichloromethane; at 20 ℃; for 1h; Inert atmosphere;

DOI:10.1016/j.tetlet.2021.153010

Reference yield: 45.0%

methyl onate (134699-90-4) → methyl 5-acetamido-2,6-anhydro-4-O-benzoyl-3,5-dideoxy-8,9-O-isopropylidene-D-glycero-D-galacto-non-2-enoate (134699-92-6) + methyl (5-acetamido-2,7-anhydro-4-O-benzoyl-3,5-dideoxy-8,9-isopropylidene-α-D-glycero-D-galacto-2-nonulopyranosid)onate (134699-91-5)

Guidance literature:

With dichloro bis(acetonitrile) palladium(II); silver trifluoromethanesulfonate; In dichloromethane;

DOI:10.1248/cpb.39.817

Reference yield:

methyl 5-acetamido, 3,5-dideoxy-8,9-O-isopropylidene-Dglycero-β-D-galacto-2-nonulopyranosonate (114857-70-4) → methyl 5-acetamido-2,6-anhydro-4-O-benzoyl-3,5-dideoxy-8,9-O-isopropylidene-D-glycero-D-galacto-non-2-enoate (134699-92-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 85 percent / pyridine

2: 75 percent / 4-N,N-dimethylaminopyridine / acetonitrile

3: 40 percent / AgOTf / (MeCN)2Pd(II)Cl₂ / MS 4A / CH₂Cl₂

With pyridine; dmap; dichloro bis(acetonitrile) palladium(II); silver trifluoromethanesulfonate; In dichloromethane; acetonitrile;

DOI:10.1248/cpb.39.817

upstream raw materials:

methyl onate

methyl 5-acetamido, 3,5-dideoxy-8,9-O-isopropylidene-Dglycero-β-D-galacto-2-nonulopyranosonate

(2S,4S,5R,6R)-5-Acetylamino-4-benzoyloxy-6-[(S)-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-hydroxy-methyl]-2-hydroxy-tetrahydro-pyran-2-carboxylic acid methyl ester

benzoic acid anhydride

Downstream raw materials:

methyl 5-acetamido-2,6-anhydro-4-O-benzoyl-7-O-(tert-butyldimethylsilyl)-3,5-dideoxy-8,9-O-isopropylidene-D-glycero-D-galacto-non-2-enoate