methyl (methyl-2,3-bis-O-(phenylmethyl)-β-D-glucopyranoside)uronate

Base Information

• Chemical Name: methyl (methyl-2,3-bis-O-(phenylmethyl)-β-D-glucopyranoside)uronate
• CAS No.: 148312-82-7
• Molecular Formula: C₂₂H₂₆O₇
• Molecular Weight: 402.444
• Mol file: 148312-82-7.mol

Synonyms:methyl (methyl-2,3-bis-O-(phenylmethyl)-β-D-glucopyranoside)uronate

Chemical Property of methyl (methyl-2,3-bis-O-(phenylmethyl)-β-D-glucopyranoside)uronate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (methyl-2,3-bis-O-(phenylmethyl)-β-D-glucopyranoside)uronate

There total 10 articles about methyl (methyl-2,3-bis-O-(phenylmethyl)-β-D-glucopyranoside)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: 94.0%

diazomethane (186581-53-3,908094-01-9,334-88-3) + methyl 2,3-di-O-benzyl-β-D-glucopyranoside (6988-40-5,17791-36-5,29388-46-3,31873-34-4,33164-03-3,51842-19-4,52526-60-0,61117-12-2,87392-25-4,117605-35-3) → methyl (methyl-2,3-bis-O-(phenylmethyl)-β-D-glucopyranoside)uronate (148312-82-7)

Guidance literature:

methyl 2,3-di-O-benzyl-β-D-glucopyranoside; With sodium hypochlorite; sodium chlorite; 1,5-dimethyl-9-azanoradamantane N-oxyl; In aq. phosphate buffer; water; acetonitrile; for 14h; pH=6.8; Inert atmosphere;

diazomethane; Reagent/catalyst; Inert atmosphere;

DOI:10.1021/jo502426p

Reference yield: 80.0%

methyl 2,3-di-O-benzyl-β-D-glucopyranoside (6988-40-5,17791-36-5,29388-46-3,31873-34-4,33164-03-3,51842-19-4,52526-60-0,61117-12-2,87392-25-4,117605-35-3) + methyl iodide (74-88-4) → methyl (methyl-2,3-bis-O-(phenylmethyl)-β-D-glucopyranoside)uronate (148312-82-7)

Guidance literature:

methyl 2,3-di-O-benzyl-β-D-glucopyranoside; With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; In dichloromethane; water; at 20 ℃; for 2h;

methyl iodide; With potassium hydrogencarbonate; In N,N-dimethyl-formamide; at 20 ℃; for 18h; Darkness; Inert atmosphere;

DOI:10.1039/c8ob02225a

Reference yield:

methyl beta-D-glucopyranoside (709-50-2) → methyl (methyl-2,3-bis-O-(phenylmethyl)-β-D-glucopyranoside)uronate (148312-82-7)

Guidance literature:

Multi-step reaction with 4 steps

1.1: camphor-10-sulfonic acid / N,N-dimethyl-formamide / 18 h / 20 °C / pH 3 / Molecular sieve; Inert atmosphere

2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.17 h / 20 °C

2.2: 3 h / 20 °C

3.1: trifluoroacetic acid / water / 18 h / 20 °C

4.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / dichloromethane; water / 2 h / 20 °C

4.2: 18 h / 20 °C / Darkness; Inert atmosphere

With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; camphor-10-sulfonic acid; sodium hydride; trifluoroacetic acid; In dichloromethane; water; N,N-dimethyl-formamide; mineral oil;

DOI:10.1039/c8ob02225a

upstream raw materials:

methyl 2,3-di-O-benzyl-α-D-glucopyranoside

methanol

methyl 2,3-di-O-benzyl-β-D-glucopyranoside

diazomethane

Downstream raw materials:

O²,O³-dibenzyl-O¹,O⁴-dimethyl-α-D-glucopyranuronic acid methyl ester

methyl 4)-2,3-di-O-benzyl-β-D-glucopyranosid>uronate

O²,O³-dibenzyl-O¹,O⁴-dimethyl-α-D-glucopyranuronic acid amide

O¹,O⁴-dimethyl-α-D-glucopyranuronic acid amide