3-Methoxy-1-(2',3',5'-tri-O-benzyl-α-D-ribofuranosyl)-propin

Base Information

• Chemical Name: 3-Methoxy-1-(2',3',5'-tri-O-benzyl-α-D-ribofuranosyl)-propin
• CAS No.: 113794-31-3
• Molecular Formula: C₃₀H₃₂O₅
• Molecular Weight: 472.581
• Mol file: 113794-31-3.mol

Synonyms:3-Methoxy-1-(2',3',5'-tri-O-benzyl-α-D-ribofuranosyl)-propin

Chemical Property of 3-Methoxy-1-(2',3',5'-tri-O-benzyl-α-D-ribofuranosyl)-propin

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-Methoxy-1-(2',3',5'-tri-O-benzyl-α-D-ribofuranosyl)-propin

There total 3 articles about 3-Methoxy-1-(2',3',5'-tri-O-benzyl-α-D-ribofuranosyl)-propin 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:

2,3,5-tri-O-benzyl-1-O-(p-nitrobenzoyl)-β-D-ribofuranose (51450-29-4) → 3-Methoxy-1-(2',3',5'-tri-O-benzyl-α-D-ribofuranosyl)-propin (113794-31-3)

Guidance literature:

Multi-step reaction with 2 steps

1: HBr / CH₂Cl₂ / 0.42 h / Ambient temperature

2: ZnCl₂ / tetrahydrofuran; CCl₄ / 0.5 h / Heating

With hydrogen bromide; zinc(II) chloride; In tetrahydrofuran; tetrachloromethane; dichloromethane;

DOI:10.1021/ja00216a025

Reference yield:

(2R,3R,4R,5S)-3,4-Bis-benzyloxy-2-benzyloxymethyl-5-bromo-tetrahydro-furan (84471-54-5) → 3-Methoxy-1-(2',3',5'-tri-O-benzyl-β-D-ribofuranosyl)-propin (113889-67-1) + 3-Methoxy-1-(2',3',5'-tri-O-benzyl-α-D-ribofuranosyl)-propin (113794-31-3)

Guidance literature:

With zinc(II) chloride; In tetrahydrofuran; tetrachloromethane; for 0.5h; Yield given. Yields of byproduct given; Heating;

DOI:10.1021/ja00216a025

Reference yield:

2,3,5-tri-O-benzyl-D-ribofuranose (16838-89-4) → 3-Methoxy-1-(2',3',5'-tri-O-benzyl-α-D-ribofuranosyl)-propin (113794-31-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) 0.1M EtMgBr / 1.) THF, 50 deg C, 2 h, 2.) THF, 50 deg C, 2.5 h

2: 6 percent / TsCl / pyridine / 8 h / 80 °C

With ethylmagnesium bromide; p-toluenesulfonyl chloride; In pyridine;

DOI:10.1002/ardp.19943270604

upstream raw materials:

(2R,3R,4R,5S)-3,4-Bis-benzyloxy-2-benzyloxymethyl-5-bromo-tetrahydro-furan

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

2,3,5-tri-O-benzyl-1-O-(p-nitrobenzoyl)-β-D-ribofuranose

Downstream raw materials:

1,3,4,6-tetra-O-benzyl-2,5-anhydro-D-talitol

(2,3,5-tri-O-benzyl-α-D-ribosyl)methanol

α-1-(3-methoxy-1(Z)-propenyl)-2,3,5-tri-O-benzyl-α-D-ribose