phenyl 4-deoxy-5-C-methoxy-β-D-glucopyranosiduronic acid

Base Information

Chemical Name:phenyl 4-deoxy-5-C-methoxy-β-D-glucopyranosiduronic acid
CAS No.:1350467-81-0
Molecular Formula:C₁₃H₁₆O₇
Molecular Weight:284.266
Hs Code.:

Synonyms:

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Chemical Property of phenyl 4-deoxy-5-C-methoxy-β-D-glucopyranosiduronic acid

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Technology Process of phenyl 4-deoxy-5-C-methoxy-β-D-glucopyranosiduronic acid

There total 7 articles about phenyl 4-deoxy-5-C-methoxy-β-D-glucopyranosiduronic acid 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:

: 1350467-79-6
methyl (phenyl 4-deoxy-5-C-methoxy-β-D-glucopyranosid)uronate

: 1350467-81-0
phenyl 4-deoxy-5-C-methoxy-β-D-glucopyranosiduronic acid

Guidance literature:: With sodium hydroxide; In acetone; at 0 ℃; for 0.0833333h;
DOI:10.1021/ja209067v

Reference yield:

: D-glucurono-6,3-lactone

: 1350467-81-0
phenyl 4-deoxy-5-C-methoxy-β-D-glucopyranosiduronic acid

Guidance literature:: Multi-step reaction with 7 steps

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

1.2: 1.5 h / 0 °C

2.1: hydrazinium monoacetate / N,N-dimethyl-formamide / 20 °C

3.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 0.5 h / -78 °C / Molecular sieve; Inert atmosphere

4.1: boron trifluoride diethyl etherate / dichloromethane / 0.5 h / -78 °C / Molecular sieve; Inert atmosphere

5.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 20 °C / Molecular sieve; Inert atmosphere

6.1: acetyl chloride / methanol / 192 h / 20 °C / Inert atmosphere

7.1: sodium hydroxide / acetone / 0.08 h / 0 °C

With boron trifluoride diethyl etherate; sodium methylate; hydrazinium monoacetate; 1,8-diazabicyclo[5.4.0]undec-7-ene; acetyl chloride; sodium hydroxide; In methanol; dichloromethane; N,N-dimethyl-formamide; acetone;
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

: 1350467-81-0
phenyl 4-deoxy-5-C-methoxy-β-D-glucopyranosiduronic acid

Guidance literature:: Multi-step reaction with 6 steps

1: hydrazinium monoacetate / N,N-dimethyl-formamide / 20 °C

2: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 0.5 h / -78 °C / Molecular sieve; Inert atmosphere

3: boron trifluoride diethyl etherate / dichloromethane / 0.5 h / -78 °C / Molecular sieve; Inert atmosphere

4: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 20 °C / Molecular sieve; Inert atmosphere

5: acetyl chloride / methanol / 192 h / 20 °C / Inert atmosphere

6: sodium hydroxide / acetone / 0.08 h / 0 °C

With boron trifluoride diethyl etherate; hydrazinium monoacetate; 1,8-diazabicyclo[5.4.0]undec-7-ene; acetyl chloride; sodium hydroxide; In methanol; dichloromethane; N,N-dimethyl-formamide; acetone;
DOI:10.1021/ja209067v