(2R,3R,4R,5R)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)tetrahydrofuran-2-carboxylic acid

Base Information

Chemical Name:(2R,3R,4R,5R)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)tetrahydrofuran-2-carboxylic acid
CAS No.:42890-06-2
Molecular Formula:C₂₇H₂₈O₆
Molecular Weight:448.516
Hs Code.:

Synonyms:(2R,3R,4R,5R)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)tetrahydrofuran-2-carboxylic acid

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Chemical Property of (2R,3R,4R,5R)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)tetrahydrofuran-2-carboxylic acid

Chemical Property:

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Technology Process of (2R,3R,4R,5R)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)tetrahydrofuran-2-carboxylic acid

There total 7 articles about (2R,3R,4R,5R)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)tetrahydrofuran-2-carboxylic 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: 79.0%

: 82267-01-4
(2S,3S,4R,5R)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)tetrahydrofuran-2-carbonitrile

: 42890-06-2
(2R,3R,4R,5R)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)tetrahydrofuran-2-carboxylic acid

Guidance literature:: With potassium hydroxide; In methanol; for 3h; Heating;
DOI:10.1016/0008-6215(88)84056-4

Reference yield:

: 532-20-7,613-83-2,7261-25-8,7687-39-0,13221-22-2,14795-83-6,15761-67-8,20074-49-1,25545-03-3,25545-04-4,32445-75-3,34436-17-4,36441-93-7,36468-53-8,37110-85-3,37388-49-1,38029-69-5,40461-77-6,40461-89-0,41546-19-4,41546-20-7,41546-21-8,41546-26-3,41546-29-6,41546-30-9,41546-31-0,126872-16-0,131064-98-7
D-Ribose

: 42890-06-2
(2R,3R,4R,5R)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)tetrahydrofuran-2-carboxylic acid

Guidance literature:: Multi-step reaction with 6 steps

1.1: sulfuric acid / 12 h / 25 °C

2.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 0 °C

2.2: 11 h / 25 °C

3.1: trifluoroacetic acid / water / 12 h / 25 °C

4.1: dmap; triethylamine / dichloromethane / 1 h / 0 - 25 °C

5.1: boron trifluoride diethyl etherate / acetonitrile / 1 h / -35 °C

6.1: hydrogenchloride / water; 1,4-dioxane / 12 h / 80 °C

With hydrogenchloride; dmap; sulfuric acid; boron trifluoride diethyl etherate; sodium hydride; triethylamine; trifluoroacetic acid; In 1,4-dioxane; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;

Reference yield:

: 1824-96-0,1824-97-1,3795-68-4,3795-69-5,4229-54-3,5531-18-0,7473-45-2,13039-63-9,13039-64-0,13039-65-1,13039-67-3,22416-73-5,22861-09-2,25129-51-5,52485-92-4,52689-55-1,52689-56-2,56607-40-0,72880-70-7,79083-42-4,86782-30-1,86782-31-2,89615-03-2,89673-67-6,89707-99-3,102045-32-9,135910-17-7
methyl ribofuranoside

: 42890-06-2
(2R,3R,4R,5R)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)tetrahydrofuran-2-carboxylic acid

Guidance literature:: Multi-step reaction with 5 steps

1.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 0 °C

1.2: 11 h / 25 °C

2.1: trifluoroacetic acid / water / 12 h / 25 °C

3.1: dmap; triethylamine / dichloromethane / 1 h / 0 - 25 °C

4.1: boron trifluoride diethyl etherate / acetonitrile / 1 h / -35 °C

5.1: hydrogenchloride / water; 1,4-dioxane / 12 h / 80 °C

With hydrogenchloride; dmap; boron trifluoride diethyl etherate; sodium hydride; triethylamine; trifluoroacetic acid; In 1,4-dioxane; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;