(3R,4S,5R)-4-(benzyloxy)-5-(benzyloxymethyl)tetrahydrofuran-2,3-diol

Base Information

• Chemical Name: (3R,4S,5R)-4-(benzyloxy)-5-(benzyloxymethyl)tetrahydrofuran-2,3-diol
• CAS No.: 561055-45-6
• Molecular Formula: C₁₉H₂₂O₅
• Molecular Weight: 330.381
• Mol file: 561055-45-6.mol

Synonyms:(3R,4S,5R)-4-(benzyloxy)-5-(benzyloxymethyl)tetrahydrofuran-2,3-diol

Chemical Property of (3R,4S,5R)-4-(benzyloxy)-5-(benzyloxymethyl)tetrahydrofuran-2,3-diol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,4S,5R)-4-(benzyloxy)-5-(benzyloxymethyl)tetrahydrofuran-2,3-diol

There total 9 articles about (3R,4S,5R)-4-(benzyloxy)-5-(benzyloxymethyl)tetrahydrofuran-2,3-diol 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:

3,5-O-dibenzyloxy-1,2-O-isorpopylidene-α-D-ribofuranose (55735-86-9) → (3R,4S,5R)-4-(benzyloxy)-5-(benzyloxymethyl)tetrahydrofuran-2,3-diol (16054-77-6) + (3R,4S,5R)-4-(benzyloxy)-5-(benzyloxymethyl)tetrahydrofuran-2,3-diol (561055-45-6)

Guidance literature:

With sulfuric acid; water; In 1,4-dioxane; for 3h; Reflux;

DOI:10.1016/j.bmc.2012.09.006

Reference yield:

3,5-O-dibenzyloxy-1,2-O-isorpopylidene-α-D-ribofuranose (55735-86-9) → (3R,4S,5R)-4-(benzyloxy)-5-(benzyloxymethyl)tetrahydrofuran-2,3-diol (561055-45-6)

Guidance literature:

With trifluoroacetic acid;

DOI:10.1016/S0040-4039(00)97734-7

Reference yield:

1,2-isopropylidene-α-D-ribofuranose (37077-81-9) → (3R,4S,5R)-4-(benzyloxy)-5-(benzyloxymethyl)tetrahydrofuran-2,3-diol (16054-77-6) + (3R,4S,5R)-4-(benzyloxy)-5-(benzyloxymethyl)tetrahydrofuran-2,3-diol (561055-45-6)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium hydride / N,N-dimethyl-formamide; paraffin oil / 2 h / 0 °C

2: water; sulfuric acid / 1,4-dioxane / 3 h / Reflux

With sulfuric acid; water; sodium hydride; In 1,4-dioxane; N,N-dimethyl-formamide; paraffin oil;

DOI:10.1016/j.bmc.2012.09.006

upstream raw materials:

3,5-O-dibenzyloxy-1,2-O-isorpopylidene-α-D-ribofuranose

benzyl bromide

5-O-(tert-butyldimethylsilyl)-1,2-O-isopropylidene-α-D-erythro-pentofuranos-3-ulose

1,2-O-isopropylidene-5-O-(tert-butyl)dimethylsilyl-α-D-ribofuranoside

Downstream raw materials:

3,5-di-O-benzyl-D-ribo-penta-1,4-lactone

3,5-di-O-benzyl-1,2-O-thiocarbonyl-α-D-ribo-furanose

1,3,5-tri-O-benzyl-α-D-ribofuranose

1-(3',5'-di-O-benzyl-β-D-ribo-furanosyl)thymine