5-O-benzyl-1,2,3-tri-O-acetyl-α-D-ribofuranoside

Base Information

• Chemical Name: 5-O-benzyl-1,2,3-tri-O-acetyl-α-D-ribofuranoside
• CAS No.: 124151-36-6
• Molecular Formula: C₁₈H₂₂O₈
• Molecular Weight: 366.368
• Mol file: 124151-36-6.mol

Synonyms:

Chemical Property of 5-O-benzyl-1,2,3-tri-O-acetyl-α-D-ribofuranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-O-benzyl-1,2,3-tri-O-acetyl-α-D-ribofuranoside

There total 6 articles about 5-O-benzyl-1,2,3-tri-O-acetyl-α-D-ribofuranoside 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:

acetic anhydride (108-24-7) + 3,5-O-dibenzyloxy-1,2-O-isorpopylidene-α-D-ribofuranose (55735-86-9) → 5-O-benzyl-1,2,3-tri-O-acetyl-β-D-ribofuranoside (118964-37-7) + 5-O-benzyl-1,2,3-tri-O-acetyl-α-D-ribofuranoside (118964-37-7,124151-36-6)

Guidance literature:

With sulfuric acid; acetic acid; In dichloromethane; at 20 ℃; for 8h; Overall yield = 76 percent; Overall yield = 1.5 g;

DOI:10.1016/j.carres.2020.108178

Reference yield:

(2R,3R,4R,5R)-2-benzyloxymethyl-3,4-isopropylidenedioxy-5-methoxytetrahydrofuran (33019-63-5) → 5-O-benzyl-1,2,3-tri-O-acetyl-D-ribofuranoside (124151-36-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 70percent aq. acetic acid / 6 h / 80 °C

2: pyridine, DMAP / CH₂Cl₂ / 0.5 h

With pyridine; dmap; acetic acid; In dichloromethane;

DOI:10.1016/S0040-4020(01)97590-8

Reference yield:

((3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methanol (4099-85-8,828937-29-7) → 5-O-benzyl-1,2,3-tri-O-acetyl-D-ribofuranoside (124151-36-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 90 percent / sodium hydride, tetra-n-butylammonium iodide / tetrahydrofuran / 6 h / Ambient temperature

2: 70percent aq. acetic acid / 6 h / 80 °C

3: pyridine, DMAP / CH₂Cl₂ / 0.5 h

With pyridine; dmap; tetra-(n-butyl)ammonium iodide; sodium hydride; acetic acid; In tetrahydrofuran; dichloromethane;

DOI:10.1016/S0040-4020(01)97590-8

upstream raw materials:

5-O-benzyl-D-ribofuranose

acetic anhydride

(2R,3R,4R,5R)-2-benzyloxymethyl-3,4-isopropylidenedioxy-5-methoxytetrahydrofuran

((3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methanol

Downstream raw materials:

Diisopropyl-phosphoramidous acid (2R,3R,4R)-4-benzyloxy-2-benzyloxymethyl-5-{(2S,3R,4R)-2,3,4-tris-benzyloxy-5-[(4-methoxy-phenyl)-diphenyl-methoxy]-pentyloxy}-tetrahydro-furan-3-yl ester 2-cyano-ethyl ester

2,5-di-O-benzyl-3-O-levulinyl-β-ribofuranosyl 2,3,4-tri-O-benzyl-5-O-monomethoxytrityl-D-ribitol

2,5-di-O-benzyl-β-D-ribofuranosyl 2,3,4-tri-O-benzyl-5-O-monomethoxytrityl-D-ribitol

2,5-di-O-benzyl-3-O-levulinyl-β-ribofuranosyl 2,3,4-tri-O-benzyl-D-ribitol

Refernces

• 1、 Chan,Just. "Synthese of oligomers of the capsular polysaccharide of the Haemophilus influenzae type b bacteria". . p. 151 - 162. Retrieved 2007/10/02.