methyl 3,4-di-O-benzyl-[(S)-1,2-O-(1-ethoxyethylidene)]-α-D-glucopyranuronate

Base Information

• Chemical Name: methyl 3,4-di-O-benzyl-[(S)-1,2-O-(1-ethoxyethylidene)]-α-D-glucopyranuronate
• CAS No.: 666238-21-7
• Molecular Formula: C₂₅H₃₀O₈
• Molecular Weight: 458.508
• Mol file: 666238-21-7.mol

Synonyms:

Chemical Property of methyl 3,4-di-O-benzyl-[(S)-1,2-O-(1-ethoxyethylidene)]-α-D-glucopyranuronate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 3,4-di-O-benzyl-[(S)-1,2-O-(1-ethoxyethylidene)]-α-D-glucopyranuronate

There total 1 articles about methyl 3,4-di-O-benzyl-[(S)-1,2-O-(1-ethoxyethylidene)]-α-D-glucopyranuronate 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:

3,4-di-O-benzyl-6-O-tert-butyldimethylsilyl-[(S)-1,2-O-(1-ethoxyethylidene)]-α-D-glucopyranose (666237-84-9) → methyl 3,4-di-O-benzyl-[(S)-1,2-O-(1-ethoxyethylidene)]-α-D-glucopyranuronate (666238-21-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 96 percent / tetrabutylammonium fluoride trihydrate / tetrahydrofuran / 0.5 h / 20 °C

2.1: 2,2,6,6-tetramethylpiperidine 1-oxide (TEMPO); KBr; aq. NaOCl / tetrabutylammonium chloride; aq. NaHCO₃ / CH₂Cl₂ / 0.5 h / 20 °C

2.2: 65 percent / tetrabutylammonium bromide; aq. NaHCO₃ / CH₂Cl₂

With sodium hypochlorite; TEMPO; tetrabutyl ammonium fluoride; potassium bromide; tetrabutyl-ammonium chloride; sodium hydrogencarbonate; In tetrahydrofuran; dichloromethane;

DOI:10.1081/CAR-120026603

Reference yield: 28.0%

(5R)-2,3,4,5-tetrahydro-5-hydroxymethyl-2-furanone (52813-63-5) + methyl 3,4-di-O-benzyl-[(S)-1,2-O-(1-ethoxyethylidene)]-α-D-glucopyranuronate (666238-21-7) → methyl [(2-R)-2,3,4,5-tetrahydro-5-oxo-2-furylmethyl 2-O-acetyl-3,4-di-O-benzyl-β-D-glucopyranosid]uronate (666238-73-9)

Guidance literature:

(5R)-2,3,4,5-tetrahydro-5-hydroxymethyl-2-furanone; methyl 3,4-di-O-benzyl-[(S)-1,2-O-(1-ethoxyethylidene)]-α-D-glucopyranuronate; With toluene-4-sulfonic acid; In 1,2-dichloro-ethane; for 1h;

With pyridinium perchlorate; for 2h; Heating;

DOI:10.1081/CAR-120026603

Reference yield:

methyl 3,4-di-O-benzyl-[(S)-1,2-O-(1-ethoxyethylidene)]-α-D-glucopyranuronate (666238-21-7) → methyl 2-O-acetyl-3,4-di-O-benzyl-α-D-glucopyranosyluronate bromide (666238-29-5)

Guidance literature:

With Acetyl bromide; tetraethylammonium bromide; In dichloromethane; at 20 ℃; for 2h;

DOI:10.1081/CAR-120026603

upstream raw materials:

3,4-di-O-benzyl-6-O-tert-butyldimethylsilyl-[(S)-1,2-O-(1-ethoxyethylidene)]-α-D-glucopyranose

Downstream raw materials:

methyl [(2-R)-2,3,4,5-tetrahydro-5-oxo-2-furylmethyl 2-O-acetyl-3,4-di-O-benzyl-β-D-glucopyranosid]uronate

methyl 2-O-acetyl-3,4-di-O-benzyl-α-D-glucopyranosyluronate bromide

methyl 3,4-di-O-benzyl-[(S)-1,2-O-(1-cyanoethylidene)]-α-D-glucopyranuronate

(2-R)-2,3,4,5-tetrahydro-5-oxo-2-furylmethyl 3,4-di-O-benzyl-β-D-glucopyranosiduronic acid