methyl 3,5-dibenzoyloxy-2-deoxy-β-D-erythropentofuranoside

Base Information

• Chemical Name: methyl 3,5-dibenzoyloxy-2-deoxy-β-D-erythropentofuranoside
• CAS No.: 51785-70-7
• Molecular Formula: C₂₀H₂₀O₆
• Molecular Weight: 356.375
• Mol file: 51785-70-7.mol

Synonyms:methyl 3,5-dibenzoyloxy-2-deoxy-β-D-erythropentofuranoside

Chemical Property of methyl 3,5-dibenzoyloxy-2-deoxy-β-D-erythropentofuranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 3,5-dibenzoyloxy-2-deoxy-β-D-erythropentofuranoside

There total 14 articles about methyl 3,5-dibenzoyloxy-2-deoxy-β-D-erythropentofuranoside 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: 74.0%

C20H22O5 → methyl 3,5-dibenzoyloxy-2-deoxy-β-D-erythropentofuranoside (51785-70-7)

Guidance literature:

With air; eosin Y-sensitized titanium dioxide; In acetone; at 20 ℃; for 12h;

DOI:10.1021/acscatal.7b03029

Reference yield:

benzoyl chloride (98-88-4) + 1-O-methyl-2-deoxy-D-ribofuranoside (51255-17-5,51255-18-6,60134-26-1,89577-26-4,96038-80-1,96039-31-5,144301-84-8,144301-85-9) → methyl 3,5-dibenzoyloxy-2-deoxy-β-D-erythropentofuranoside (51785-70-7) + methyl 3,5-dibenzoyloxy-2-deoxy-α-D-erythropentofuranoside (80339-59-9)

Guidance literature:

In pyridine; at 23 ℃;

DOI:10.1016/S0040-4039(00)94998-0

Reference yield:

L-arabinose (5328-37-0) → methyl 3,5-di-O-benzoyl-2-deoxy-L-erythro-pentofuranoside (51785-70-7,80339-59-9,102303-03-7,102303-04-8,108647-88-7)

Guidance literature:

Multi-step reaction with 6 steps

1: 49 percent / imidazole / dimethylformamide

2: 67 percent / CuSO₄, H₂SO₄

3: 89 percent / Bu₄NF / tetrahydrofuran

4: 82 percent / pyridine / 3 h / Ambient temperature

5: 89 percent / I₂ / Heating

6: 1) phenyl chlorothionocarbonate, 4-(dimethylamino)pyridine, 2) Bu₃SnH, AIBN / 1) CH₂Cl₂, r.t., 0.5 h, 2) toluene, 80 deg C, 3 h

With pyridine; 1H-imidazole; dmap; 2,2'-azobis(isobutyronitrile); sulfuric acid; tetrabutyl ammonium fluoride; iodine; tri-n-butyl-tin hydride; copper(II) sulfate; phenylcarbonochloridothioate; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1016/0008-6215(92)84166-P

upstream raw materials:

(2S,3R)-2-Hydroxymethyl-5-methoxy-tetrahydro-furan-3-ol

benzoyl chloride

1-O-methyl-2-deoxy-D-ribofuranoside

2-deoxy-D-ribose

Downstream raw materials:

1-(2-deoxy-3,5-di-O-benzoyl-β-L-erythro-pentofuranosyl)-5-fluorouracil

C₂₃H₂₄O₇

1-O-acetyl-3,5-di-O-benzoyl-2-deoxy-α-L-erythro-pentofuranoside

1-O-acetyl-3,5-di-O-benzoyl-2-deoxy-β-L-erythro-pentofuranoside

Refernces

• 1、 Adamo, Mauro F.A.,Adlington, Robert M.,Baldwin, Jack E.,Day, Anna L.. "A parallel synthesis approach towards a family of C-nucleosides". . p. 841 - 849. Retrieved 2007/10/03.
• 2、 Fronza, Giovanni,Fuganti, Claudio,Grasselli, Piero,Servi, Stefano. "BAKER'S YEAST MEDIATED PREPARATION OF CARBOHYDRATE-LIKE CHIRAL SYNTHONS". . p. 4961 - 4964. Retrieved 2007/10/02.