methyl (benzyl 4,7,8,9-tetra-O-acetyl-3,5-dideoxy-5-valeroylamino-D-glycero-α-D-galacto-2-nonulopyranosid)onate

Base Information

Chemical Name:methyl (benzyl 4,7,8,9-tetra-O-acetyl-3,5-dideoxy-5-valeroylamino-D-glycero-α-D-galacto-2-nonulopyranosid)onate
CAS No.:284036-91-5
Molecular Formula:C₃₀H₄₁NO₁₃
Molecular Weight:623.654
Hs Code.:

Synonyms:methyl (benzyl 4,7,8,9-tetra-O-acetyl-3,5-dideoxy-5-valeroylamino-D-glycero-α-D-galacto-2-nonulopyranosid)onate

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Chemical Property of methyl (benzyl 4,7,8,9-tetra-O-acetyl-3,5-dideoxy-5-valeroylamino-D-glycero-α-D-galacto-2-nonulopyranosid)onate

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Technology Process of methyl (benzyl 4,7,8,9-tetra-O-acetyl-3,5-dideoxy-5-valeroylamino-D-glycero-α-D-galacto-2-nonulopyranosid)onate

There total 3 articles about methyl (benzyl 4,7,8,9-tetra-O-acetyl-3,5-dideoxy-5-valeroylamino-D-glycero-α-D-galacto-2-nonulopyranosid)onate 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: 71.0%

: methyl (benzyl 4,7,8,9-tetra-O-acetyl-5-amino-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosid)onate hydrochloride

: 109-52-4
valeric acid

: 284036-91-5
methyl (benzyl 4,7,8,9-tetra-O-acetyl-3,5-dideoxy-5-valeroylamino-D-glycero-α-D-galacto-2-nonulopyranosid)onate

Guidance literature:: With N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; In dichloromethane; at 0 ℃;
DOI:10.1002/(SICI)1099-0690(200004)2000:8<1467::AID-EJOC1467>3.0.CO;2-E

Reference yield:

: 19342-75-7
methyl (benzyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosid)onate

: 284036-91-5
methyl (benzyl 4,7,8,9-tetra-O-acetyl-3,5-dideoxy-5-valeroylamino-D-glycero-α-D-galacto-2-nonulopyranosid)onate

Guidance literature:: Multi-step reaction with 3 steps

1: 50 percent / Tf₂O; 2,6-di-tert-butylpyridine / acetonitrile / -25 °C

2: 95 percent / CF₃CO₂H / methanol / 2 h / 0 °C

3: 71 percent / Et₃N; water-soluble carbodiimide (WSC) / CH₂Cl₂ / 0 °C

With 2,6-di-tert-butyl-pyridine; trifluoromethylsulfonic anhydride; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; trifluoroacetic acid; In methanol; dichloromethane; acetonitrile; 1: Alkylation / 2: Hydrolysis / 3: Acylation;
DOI:10.1002/(SICI)1099-0690(200004)2000:8<1467::AID-EJOC1467>3.0.CO;2-E

Reference yield:

: 284037-41-8
(2R,4S,5R,6R)-4-Acetoxy-2-benzyloxy-5-[1-ethoxy-eth-(Z)-ylideneamino]-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester

: 284036-91-5
methyl (benzyl 4,7,8,9-tetra-O-acetyl-3,5-dideoxy-5-valeroylamino-D-glycero-α-D-galacto-2-nonulopyranosid)onate

Guidance literature:: Multi-step reaction with 2 steps

1: 95 percent / CF₃CO₂H / methanol / 2 h / 0 °C

2: 71 percent / Et₃N; water-soluble carbodiimide (WSC) / CH₂Cl₂ / 0 °C

With N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; trifluoroacetic acid; In methanol; dichloromethane; 1: Hydrolysis / 2: Acylation;
DOI:10.1002/(SICI)1099-0690(200004)2000:8<1467::AID-EJOC1467>3.0.CO;2-E