2-O-glucopyranosylribitol-4'-phosphate

Base Information

• Chemical Name: 2-O-glucopyranosylribitol-4'-phosphate
• CAS No.: 121496-69-3
• Molecular Formula: C₁₁H₂₃O₁₃P
• Molecular Weight: 394.27
• Mol file: 121496-69-3.mol

Synonyms:2-O-glucopyranosylribitol-4’-phosphate

Chemical Property of 2-O-glucopyranosylribitol-4'-phosphate

Chemical Property:

• Boiling Point: 847.9°Cat760mmHg
• Flash Point: 466.6°C
• PSA: 236.64000
• Density: 1.8g/cm³
• LogP: -5.00510

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2-O-glucopyranosylribitol-4'-phosphate

There total 7 articles about 2-O-glucopyranosylribitol-4'-phosphate 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: 100.0%

Phosphoric acid (2R,3R,4R,5R,6R)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-((1R,2S,3S)-2,3,4-tris-benzyloxy-1-hydroxymethyl-butoxy)-tetrahydro-pyran-3-yl ester diphenyl ester (116490-85-8) → 2-O-β-D-Glucopyranosyl-L-ribitol 4'-phosphate (121496-69-3)

Guidance literature:

With hydrogen; platinum(IV) oxide; palladium on activated charcoal; In ethanol; ethyl acetate; for 48h;

DOI:10.1016/0008-6215(88)84144-2

Reference yield:

2,3-di-O-acetyl-4,6-O-ethylidene-α-D-glucopyranosyl bromide (116490-77-8) → 2-O-β-D-Glucopyranosyl-L-ribitol 4'-phosphate (121496-69-3)

Guidance literature:

Multi-step reaction with 7 steps

1: 86 percent / mercuric bromode, mercuric cyanide, pulverised molecular sieves (3 A) / benzene; nitromethane

2: 70 percent / sodium hydride 50 percent disp. in oil / dimethylformamide / 1.5 h / Ambient temperature

3: 80 percent / Dowex 50W-X₄ (H+) resin / methanol / 6 h / Heating

4: 49 percent / aqueous 5percent sodium hydroxide, tetrabutylammonium bromide / CH₂Cl₂ / 19 h / Heating

5: 1.) 1,2,4-triazole, triethylamine, oxolane; 2.) 4-dimethylaminopyridine / 1.) 10 min at 10 deg C, 45 min at R_.T_.; 2.) pyridine, 1.5 h at 40 deg C

6: 74 percent / palladium dichloride, sodium acetate / H₂O; acetic acid / 40 °C

7: 100 percent / H₂ / Pd/C, platinum oxide / ethanol; ethyl acetate / 48 h

With tetrahydrofuran; 1,2,4-Triazole; dmap; sodium hydroxide; 3 A molecular sieve; Dowex 50W-X₄ (H+) resin; tetrabutylammomium bromide; hydrogen; sodium acetate; mercury(II) cyanide; sodium hydride; triethylamine; mercury dibromide; palladium dichloride; platinum(IV) oxide; palladium on activated charcoal; In methanol; nitromethane; ethanol; dichloromethane; water; acetic acid; ethyl acetate; N,N-dimethyl-formamide; benzene;

DOI:10.1016/0008-6215(88)84144-2

Reference yield:

5-O-allyl-1,2,3-tri-O-benzyl-4-O-(2,3-di-O-acetyl-4,6-O-ethylidene-β-D-glucopyranosyl)-D-ribitol (116490-78-9) → 2-O-β-D-Glucopyranosyl-L-ribitol 4'-phosphate (121496-69-3)

Guidance literature:

Multi-step reaction with 6 steps

1: 70 percent / sodium hydride 50 percent disp. in oil / dimethylformamide / 1.5 h / Ambient temperature

2: 80 percent / Dowex 50W-X₄ (H+) resin / methanol / 6 h / Heating

3: 49 percent / aqueous 5percent sodium hydroxide, tetrabutylammonium bromide / CH₂Cl₂ / 19 h / Heating

4: 1.) 1,2,4-triazole, triethylamine, oxolane; 2.) 4-dimethylaminopyridine / 1.) 10 min at 10 deg C, 45 min at R_.T_.; 2.) pyridine, 1.5 h at 40 deg C

5: 74 percent / palladium dichloride, sodium acetate / H₂O; acetic acid / 40 °C

6: 100 percent / H₂ / Pd/C, platinum oxide / ethanol; ethyl acetate / 48 h

With tetrahydrofuran; 1,2,4-Triazole; dmap; sodium hydroxide; Dowex 50W-X₄ (H+) resin; tetrabutylammomium bromide; hydrogen; sodium acetate; sodium hydride; triethylamine; palladium dichloride; platinum(IV) oxide; palladium on activated charcoal; In methanol; ethanol; dichloromethane; water; acetic acid; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1016/0008-6215(88)84144-2

upstream raw materials:

Phosphoric acid (2R,3R,4R,5R,6R)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-((1R,2S,3S)-2,3,4-tris-benzyloxy-1-hydroxymethyl-butoxy)-tetrahydro-pyran-3-yl ester diphenyl ester

2,3-di-O-acetyl-4,6-O-ethylidene-α-D-glucopyranosyl bromide

5-O-allyl-1,2,3-tri-O-benzyl-4-O-(2,3-di-O-acetyl-4,6-O-ethylidene-β-D-glucopyranosyl)-D-ribitol

5-O-allyl-1,2,3-tri-O-benzyl-4-O-(2,3-di-O-benzyl-β-D-glucopyranosyl)-D-ribitol

Refernces