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

Base Information

• Chemical Name: methyl 3,5-dibenzoyloxy-2-deoxy-α-D-erythropentofuranoside
• CAS No.: 80339-59-9
• Molecular Formula: C₂₀H₂₀O₆
• Molecular Weight: 356.375
• Mol file: 80339-59-9.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

There total 15 articles about methyl 3,5-dibenzoyloxy-2-deoxy-α-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:

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:

1-O-methyl-β-2-deoxy-D-erythro-pentofuranose (51255-18-6) + benzoyl chloride (98-88-4) → methyl 3,5-dibenzoyloxy-2-deoxy-α-D-erythropentofuranoside (80339-59-9)

Guidance literature:

With triethylamine; In dichloromethane; at 0 - 20 ℃; for 14h; Inert atmosphere;

DOI:10.1002/asia.201901695

Reference yield:

2-Deoxy-D-ribose (533-67-5) → methyl 3,5-dibenzoyloxy-2-deoxy-α-D-erythropentofuranoside (80339-59-9)

Guidance literature:

Multi-step reaction with 2 steps

1: hydrogenchloride / diethyl ether / 3 h / 20 °C

2: triethylamine / dichloromethane / 14 h / 0 - 20 °C / Inert atmosphere

With hydrogenchloride; triethylamine; In diethyl ether; dichloromethane;

DOI:10.1002/asia.201901695

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:

3,5-O-bis(4-chlorobenzoyl)-2-deoxy-α-D-ribofuranosyl chloride

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

C₁₉H₁₈O₆

1-O-acetyl-3,5-di-O-benzoyl-2-deoxy-α-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.