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

Base Information

Chemical Name:(2-R)-2,3,4,5-tetrahydro-5-oxo-2-furylmethyl 3,4-di-O-benzyl-β-D-glucopyranosiduronic acid
CAS No.:666238-86-4
Molecular Formula:C₂₅H₂₈O₉
Molecular Weight:472.492
Hs Code.:

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

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

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

There total 18 articles about (2-R)-2,3,4,5-tetrahydro-5-oxo-2-furylmethyl 3,4-di-O-benzyl-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: 88.0%

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

: 666238-86-4
(2-R)-2,3,4,5-tetrahydro-5-oxo-2-furylmethyl 3,4-di-O-benzyl-β-D-glucopyranosiduronic acid

Guidance literature:: With lithium hydroxide; In acetone; at 20 ℃; for 3h;
DOI:10.1081/CAR-120026603

Reference yield:

: 666237-80-5
6-O-tert-butyldimethylsilyl-[(S)-1,2-O-(1-ethoxyethylidene)]-α-D-glucopyranose

: 666238-86-4
(2-R)-2,3,4,5-tetrahydro-5-oxo-2-furylmethyl 3,4-di-O-benzyl-β-D-glucopyranosiduronic acid

Guidance literature:: Multi-step reaction with 11 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

11.1: 88 percent / aq. LiOH / acetone / 3 h / 20 °C

With pyridine; chromium(VI) oxide; hydrogenchloride; lithium hydroxide; 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:

: 97673-01-3
1,2-O-<1-(exo-ethoxy)ethylidene>-α-D-glucopyranose

: 666238-86-4
(2-R)-2,3,4,5-tetrahydro-5-oxo-2-furylmethyl 3,4-di-O-benzyl-β-D-glucopyranosiduronic acid

Guidance literature:: Multi-step reaction with 12 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

12.1: 88 percent / aq. LiOH / acetone / 3 h / 20 °C

With pyridine; chromium(VI) oxide; hydrogenchloride; dmap; lithium hydroxide; 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