1-O-Acetyl-2,3,5-tri-O-benzyl-D-ribofuranose

Base Information

• Chemical Name: 1-O-Acetyl-2,3,5-tri-O-benzyl-D-ribofuranose
• CAS No.: 58381-23-0
• Molecular Formula: C28H30 O6
• Molecular Weight: 462.543
• Hs Code.: 2932190090
• DSSTox Substance ID: DTXSID90556349
• Nikkaji Number: J2.285.804A
• Mol file: 58381-23-0.mol

Synonyms:1-O-Acetyl-2,3,5-tri-O-benzyl-D-ribofuranose;58381-23-0;[(3R,4R,5R)-3,4-bis(phenylmethoxy)-5-(phenylmethoxymethyl)oxolan-2-yl] acetate;(3R,4R,5R)-3,4-Bis(benzyloxy)-5-((benzyloxy)methyl)tetrahydrofuran-2-yl acetate;D-Ribofuranose, 2,3,5-tris-O-(phenylmethyl)-, acetate;DTXSID90556349;(3R,4R,5R)-3,4-bis(benzyloxy)-5-(benzyloxymethyl)tetrahydrofuran-2-yl acetate;(3R,4R,5R)-3,4-BIS(BENZYLOXY)-5-[(BENZYLOXY)METHYL]OXOLAN-2-YL ACETATE;AKOS016010561;BS-28920;D87696;W-203188

Chemical Property of 1-O-Acetyl-2,3,5-tri-O-benzyl-D-ribofuranose

Chemical Property:

• PSA: 63.22000
• LogP: 4.66200
• Storage Temp.: Refrigerator
• Solubility.: Chloroform, Ethyl Acetate
• XLogP3: 4.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 12
• Exact Mass: 462.20423867
• Heavy Atom Count: 34
• Complexity: 579

Purity/Quality:

98%, ^*data from raw suppliers

1-O-Acetyl-2,3,5-tri-O-benzyl-D-ribofuranose ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OC1C(C(C(O1)COCC2=CC=CC=C2)OCC3=CC=CC=C3)OCC4=CC=CC=C4
• Isomeric SMILES: CC(=O)OC1[C@@H]([C@@H]([C@H](O1)COCC2=CC=CC=C2)OCC3=CC=CC=C3)OCC4=CC=CC=C4

Technology Process of 1-O-Acetyl-2,3,5-tri-O-benzyl-D-ribofuranose

There total 4 articles about 1-O-Acetyl-2,3,5-tri-O-benzyl-D-ribofuranose 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: 78.97%

2,3,5-tri-O-benzyl-D-ribofuranose (16838-89-4) + acetic anhydride (108-24-7) → (3R,4R,5R)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)tetrahydrofuran-2-yl acetate (58381-23-0)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 0 - 25 ℃; for 1h;

Reference yield:

D-Ribose (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) → (3R,4R,5R)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)tetrahydrofuran-2-yl acetate (58381-23-0)

Guidance literature:

Multi-step reaction with 4 steps

1: acetyl chloride / 20 °C

2: potassium hydroxide; tetra(n-butyl)ammonium hydrogensulfate / tetrahydrofuran / 12 h / Reflux

3: acetic acid; hydrogenchloride / 1.5 h / 65 °C

4: pyridine

With pyridine; hydrogenchloride; tetra(n-butyl)ammonium hydrogensulfate; acetic acid; acetyl chloride; potassium hydroxide; In tetrahydrofuran;

Reference yield:

methyl ribofuranoside (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) → (3R,4R,5R)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)tetrahydrofuran-2-yl acetate (58381-23-0)

Guidance literature:

Multi-step reaction with 3 steps

1: potassium hydroxide; tetra(n-butyl)ammonium hydrogensulfate / tetrahydrofuran / 12 h / Reflux

2: acetic acid; hydrogenchloride / 1.5 h / 65 °C

3: pyridine

With pyridine; hydrogenchloride; tetra(n-butyl)ammonium hydrogensulfate; acetic acid; potassium hydroxide; In tetrahydrofuran;

upstream raw materials:

2,3,5-tri-O-benzyl-D-ribofuranose

acetic anhydride

D-Ribose

methyl ribofuranoside

Downstream raw materials:

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

methyl 6-O-(2,3,5-tri-O-benzyl-β-D-ribofuranosyl)-2,3,4-tri-O-benzyl-α-D-glucopyranoside

4-penten-1-yl 2,3,5-tri-O-benzyl-β-D-ribofuranoside

Refernces

• 1、 -. "COMPOUNDS, PHARMACEUTICAL COMPOSITIONS AND USE THEREOF AS INHIBITORS OF RAN GTPASE". Paragraph 0071. . Retrieved 2019/04/09.