methyl (phenyl 2,3-di-O-acetyl-4-deoxy-1-thio-α-L-threo-hex-4-enopyranosid)uronate

Base Information

Chemical Name:methyl (phenyl 2,3-di-O-acetyl-4-deoxy-1-thio-α-L-threo-hex-4-enopyranosid)uronate
CAS No.:1350467-71-8
Molecular Formula:C₁₇H₁₈O₇S
Molecular Weight:366.392
Hs Code.:

Synonyms:methyl (phenyl 2,3-di-O-acetyl-4-deoxy-1-thio-α-L-threo-hex-4-enopyranosid)uronate

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Chemical Property of methyl (phenyl 2,3-di-O-acetyl-4-deoxy-1-thio-α-L-threo-hex-4-enopyranosid)uronate

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Technology Process of methyl (phenyl 2,3-di-O-acetyl-4-deoxy-1-thio-α-L-threo-hex-4-enopyranosid)uronate

There total 4 articles about methyl (phenyl 2,3-di-O-acetyl-4-deoxy-1-thio-α-L-threo-hex-4-enopyranosid)uronate 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: 56.0%

: 62812-42-4
methyl (phenyl 2,3,4-tri-O-acetyl-1-thio-β-D-glucopyranosid)uronate

: 1350467-71-8
methyl (phenyl 2,3-di-O-acetyl-4-deoxy-1-thio-α-L-threo-hex-4-enopyranosid)uronate

Guidance literature:: With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 20 ℃; Molecular sieve; Inert atmosphere;
DOI:10.1021/ja209067v

Reference yield:

: 3082-96-0,5432-32-6,7355-18-2,19231-41-5,30628-06-9,30628-07-0,40268-90-4,40268-95-9,40269-24-7,104195-05-3,108032-41-3
methyl 1,2,3,4-tetra-O-acetyl-α,β-D-glucopyranosyluronate

: 1350467-71-8
methyl (phenyl 2,3-di-O-acetyl-4-deoxy-1-thio-α-L-threo-hex-4-enopyranosid)uronate

Guidance literature:: Multi-step reaction with 3 steps

1: hydrogen bromide; acetic anhydride / dichloromethane; acetic acid / 0 - 4 °C

2: tetrabutylammomium bromide; sodium carbonate / ethyl acetate / 2 h / 20 °C

3: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 20 °C / Molecular sieve; Inert atmosphere

With tetrabutylammomium bromide; hydrogen bromide; acetic anhydride; sodium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; acetic acid; ethyl acetate;
DOI:10.1021/ja209067v

Reference yield:

: D-glucurono-6,3-lactone

: 1350467-71-8
methyl (phenyl 2,3-di-O-acetyl-4-deoxy-1-thio-α-L-threo-hex-4-enopyranosid)uronate

Guidance literature:: Multi-step reaction with 4 steps

1.1: sodium methylate / methanol / 0 - 20 °C

1.2: 1.5 h / 0 °C

2.1: hydrogen bromide; acetic anhydride / dichloromethane; acetic acid / 0 - 4 °C

3.1: tetrabutylammomium bromide; sodium carbonate / ethyl acetate / 2 h / 20 °C

4.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 20 °C / Molecular sieve; Inert atmosphere

With tetrabutylammomium bromide; hydrogen bromide; sodium methylate; acetic anhydride; sodium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In methanol; dichloromethane; acetic acid; ethyl acetate;
DOI:10.1021/ja209067v