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

Base Information

• Chemical Name: methyl [(2-R)-2,3,4,5-tetrahydro-5-oxo-2-furylmethyl 3,4-di-O-benzyl-β-D-glucopyranosid]uronate
• CAS No.: 666238-78-4
• Molecular Formula: C₂₆H₃₀O₉
• Molecular Weight: 486.519
• Mol file: 666238-78-4.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 17 articles about methyl [(2-R)-2,3,4,5-tetrahydro-5-oxo-2-furylmethyl 3,4-di-O-benzyl-β-D-glucopyranosid]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: 75.0%

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) → methyl [(2-R)-2,3,4,5-tetrahydro-5-oxo-2-furylmethyl 3,4-di-O-benzyl-β-D-glucopyranosid]uronate (666238-78-4)

Guidance literature:

With sodium methylate; In methanol; dichloromethane; at 20 ℃; for 4h;

DOI:10.1081/CAR-120026603

Reference yield:

6-O-tert-butyldimethylsilyl-[(S)-1,2-O-(1-ethoxyethylidene)]-α-D-glucopyranose (666237-80-5) → methyl [(2-R)-2,3,4,5-tetrahydro-5-oxo-2-furylmethyl 3,4-di-O-benzyl-β-D-glucopyranosid]uronate (666238-78-4)

Guidance literature:

Multi-step reaction with 10 steps

1.1: sodium hydride / dimethylformamide / 0.5 h / 0 °C

1.2: 71 percent / dimethylformamide / 2 h / 20 °C

2.1: 96 percent / tetrabutylammonium fluoride trihydrate / tetrahydrofuran / 0.5 h / 20 °C

3.1: 80 percent / pyridine / 0.5 h / 20 °C

4.1: acetyl bromide; tetraethylammonium bromide / CH₂Cl₂ / 0.5 h / 20 °C

5.1: 58 percent / tetrabutylammonium bromide / acetonitrile / 20 h / 20 °C

6.1: 69 percent / HCl / methanol; CH₂Cl₂ / 15 h / 20 °C

7.1: chrominum(VI) oxide; sulfuric acid / acetone; CH₂Cl₂ / 15 h / 20 °C

8.1: 0.34 g / CH₂Cl₂; diethyl ether

9.1: CH₂Cl₂

9.2: 69 percent / trityl perchlorate / CH₂Cl₂ / 24 h / 20 °C

10.1: 75 percent / sodium methoxide / methanol; CH₂Cl₂ / 4 h / 20 °C

With pyridine; chromium(VI) oxide; hydrogenchloride; Acetyl bromide; sulfuric acid; tetraethylammonium bromide; tetrabutyl ammonium fluoride; tetrabutylammomium bromide; sodium methylate; sodium hydride; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetone; acetonitrile;

DOI:10.1081/CAR-120026603

Reference yield:

1,2-O-<1-(exo-ethoxy)ethylidene>-α-D-glucopyranose (97673-01-3) → methyl [(2-R)-2,3,4,5-tetrahydro-5-oxo-2-furylmethyl 3,4-di-O-benzyl-β-D-glucopyranosid]uronate (666238-78-4)

Guidance literature:

Multi-step reaction with 11 steps

1.1: 87 percent / triethylamine; 4-dimethylaminopyridine / CH₂Cl₂ / 1 h / 20 °C

2.1: sodium hydride / dimethylformamide / 0.5 h / 0 °C

2.2: 71 percent / dimethylformamide / 2 h / 20 °C

3.1: 96 percent / tetrabutylammonium fluoride trihydrate / tetrahydrofuran / 0.5 h / 20 °C

4.1: 80 percent / pyridine / 0.5 h / 20 °C

5.1: acetyl bromide; tetraethylammonium bromide / CH₂Cl₂ / 0.5 h / 20 °C

6.1: 58 percent / tetrabutylammonium bromide / acetonitrile / 20 h / 20 °C

7.1: 69 percent / HCl / methanol; CH₂Cl₂ / 15 h / 20 °C

8.1: chrominum(VI) oxide; sulfuric acid / acetone; CH₂Cl₂ / 15 h / 20 °C

9.1: 0.34 g / CH₂Cl₂; diethyl ether

10.1: CH₂Cl₂

10.2: 69 percent / trityl perchlorate / CH₂Cl₂ / 24 h / 20 °C

11.1: 75 percent / sodium methoxide / methanol; CH₂Cl₂ / 4 h / 20 °C

With pyridine; chromium(VI) oxide; hydrogenchloride; dmap; Acetyl bromide; sulfuric acid; tetraethylammonium bromide; tetrabutyl ammonium fluoride; tetrabutylammomium bromide; sodium methylate; sodium hydride; triethylamine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetone; acetonitrile;

DOI:10.1081/CAR-120026603

upstream 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

1,2-O-<1-(exo-ethoxy)ethylidene>-α-D-glucopyranose

(5R)-2,3,4,5-tetrahydro-5-hydroxymethyl-2-furanone

benzyl bromide

Downstream raw materials:

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