methyl S-4-methylphenyl 5-acetoxyacetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycero-β-D-galacto-2-nonulopyranosidonate

Base Information

Chemical Name:methyl S-4-methylphenyl 5-acetoxyacetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycero-β-D-galacto-2-nonulopyranosidonate
CAS No.:381715-52-2
Molecular Formula:C₂₉H₃₇NO₁₄S
Molecular Weight:655.677
Hs Code.:

Synonyms:methyl S-4-methylphenyl 5-acetoxyacetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycero-β-D-galacto-2-nonulopyranosidonate

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Chemical Property of methyl S-4-methylphenyl 5-acetoxyacetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycero-β-D-galacto-2-nonulopyranosidonate

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Technology Process of methyl S-4-methylphenyl 5-acetoxyacetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycero-β-D-galacto-2-nonulopyranosidonate

There total 4 articles about methyl S-4-methylphenyl 5-acetoxyacetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycero-β-D-galacto-2-nonulopyranosidonate 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:

: (2R,4S,5R,6R)-4-Acetoxy-5-amino-2-p-tolylsulfanyl-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester

: 13831-31-7
Acetoxyacetyl chloride

: 381715-52-2
methyl S-4-methylphenyl 5-acetoxyacetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycero-β-D-galacto-2-nonulopyranosidonate

Guidance literature:: With 1,4-diaza-bicyclo[2.2.2]octane; In dichloromethane; at 20 ℃; for 0.5h;
DOI:10.1021/ja011382r

Reference yield:

: 358681-51-3
methyl (2-p-methylphenyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-β-D-galacto-2-thio-nonulopyranosid)onate

: 381715-52-2
methyl S-4-methylphenyl 5-acetoxyacetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycero-β-D-galacto-2-nonulopyranosidonate

Guidance literature:: Multi-step reaction with 4 steps

1: DMAP / tetrahydrofuran / 5 h / 60 °C

2: 0.377 g / NH₂NH₂*H₂O / methanol / 20 °C

3: TMSCl; PhOH / CH₂Cl₂ / 2 h / 20 °C

4: 0.118 g / DABCO / CH₂Cl₂ / 0.5 h / 20 °C

With 1,4-diaza-bicyclo[2.2.2]octane; dmap; chloro-trimethyl-silane; hydrazine hydrate; phenol; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1021/ja011382r

Reference yield:

: 381715-48-6
methyl S-4-methylphenyl 4,7,8,9-tetra-O-acetyl-5-tert-butoxycarbonylamino-3,5-dideoxy-2-thio-D-glycero-β-D-galacto-2-nonulopyranosidonate

: 381715-52-2
methyl S-4-methylphenyl 5-acetoxyacetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycero-β-D-galacto-2-nonulopyranosidonate

Guidance literature:: Multi-step reaction with 2 steps

1: TMSCl; PhOH / CH₂Cl₂ / 2 h / 20 °C

2: 0.118 g / DABCO / CH₂Cl₂ / 0.5 h / 20 °C

With 1,4-diaza-bicyclo[2.2.2]octane; chloro-trimethyl-silane; phenol; In dichloromethane;
DOI:10.1021/ja011382r