methyl (thiophenyl 5-N-butanoyl-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosyl)onate

Base Information

Chemical Name:methyl (thiophenyl 5-N-butanoyl-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosyl)onate
CAS No.:1000890-38-9
Molecular Formula:C₂₈H₃₇NO₁₂S
Molecular Weight:611.667
Hs Code.:

Synonyms:methyl (thiophenyl 5-N-butanoyl-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosyl)onate

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Chemical Property of methyl (thiophenyl 5-N-butanoyl-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosyl)onate

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Technology Process of methyl (thiophenyl 5-N-butanoyl-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosyl)onate

There total 5 articles about methyl (thiophenyl 5-N-butanoyl-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosyl)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: 45.0%

: 106-31-0
butanoic acid anhydride

: 118977-25-6,118977-26-7
methyl (phenyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-galacto-2-nonulopyranoside)onate

: 1000890-38-9
methyl (thiophenyl 5-N-butanoyl-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosyl)onate

Guidance literature:: methyl (phenyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-galacto-2-nonulopyranoside)onate; With methanesulfonic acid; In methanol; at 60 ℃; Inert atmosphere;

butanoic acid anhydride; With triethylamine; In methanol; at 0 ℃; for 2h; Inert atmosphere;
DOI:10.1002/cbic.201200471

Reference yield:

: 106-31-0
butanoic acid anhydride

: C₂HF₃O₂*C₂₄H₃₁NO₁₁S

: 1000890-38-9
methyl (thiophenyl 5-N-butanoyl-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosyl)onate

Guidance literature:: With dmap; In dichloromethane; at 20 ℃; Inert atmosphere;
DOI:10.1021/jm801609s

Reference yield:

: 19342-33-7
N-acetyl neuraminic acid

: 1000890-38-9
methyl (thiophenyl 5-N-butanoyl-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosyl)onate

Guidance literature:: Multi-step reaction with 5 steps

1.1: Dowex? [50W-X8 (H⁺)] / 16 h / 20 °C / Inert atmosphere

2.1: 16 h / 0 - 20 °C / Inert atmosphere

3.1: acetyl chloride / methanol / 16 h / 0 - 20 °C / Inert atmosphere

4.1: tetrabutylammonium hydrogen sulfate; sodium carbonate / ethyl acetate / 3 h / 20 °C / Inert atmosphere

5.1: methanesulfonic acid / methanol / 60 °C / Inert atmosphere

5.2: 2 h / 0 °C / Inert atmosphere

With tetrabutylammonium hydrogen sulfate; methanesulfonic acid; sodium carbonate; acetyl chloride; In methanol; ethyl acetate;
DOI:10.1002/cbic.201200471