Biphenyl-4-carboxylic acid (2S,5R)-5-methoxy-3-methylene-tetrahydro-furan-2-ylmethyl ester

Base Information

• Chemical Name: Biphenyl-4-carboxylic acid (2S,5R)-5-methoxy-3-methylene-tetrahydro-furan-2-ylmethyl ester
• CAS No.: 172342-53-9
• Molecular Formula: C₂₀H₂₀O₄
• Molecular Weight: 324.376
• Mol file: 172342-53-9.mol

Synonyms:Biphenyl-4-carboxylic acid (2S,5R)-5-methoxy-3-methylene-tetrahydro-furan-2-ylmethyl ester

Chemical Property of Biphenyl-4-carboxylic acid (2S,5R)-5-methoxy-3-methylene-tetrahydro-furan-2-ylmethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Biphenyl-4-carboxylic acid (2S,5R)-5-methoxy-3-methylene-tetrahydro-furan-2-ylmethyl ester

There total 4 articles about Biphenyl-4-carboxylic acid (2S,5R)-5-methoxy-3-methylene-tetrahydro-furan-2-ylmethyl ester 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: 71.0%

Methyl 2-deoxy-5-O-(4-phenylbenzoyl)-β-D-glyceropentofuranosid-3-ulose (129468-48-0) + 1,1-dibromomethane (74-95-3) → Biphenyl-4-carboxylic acid (2S,5R)-5-methoxy-3-methylene-tetrahydro-furan-2-ylmethyl ester (172342-53-9)

Guidance literature:

With titanium tetrachloride; zinc; In tetrahydrofuran; dichloromethane; 1.) 0 deg C, 15 min, 2.) r.t., 45 min;

DOI:10.1021/jo00127a041

Reference yield:

methyl 2-deoxy-5-O-(4-phenylbenzoyl)-β-D-erythro-pentofuranoside (125611-95-2) → Biphenyl-4-carboxylic acid (2S,5R)-5-methoxy-3-methylene-tetrahydro-furan-2-ylmethyl ester (172342-53-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 88 percent / pyridine, CrO₃, Ac₂O / CH₂Cl₂ / 0.25 h / Ambient temperature

2: 71 percent / Zn, TiCl₄ / CH₂Cl₂; tetrahydrofuran / 1.) 0 deg C, 15 min, 2.) r.t., 45 min

With pyridine; chromium(VI) oxide; acetic anhydride; titanium tetrachloride; zinc; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo00127a041

Reference yield:

4-biphenyl-carboxylic acid chloride (14002-51-8) → Biphenyl-4-carboxylic acid (2S,5R)-5-methoxy-3-methylene-tetrahydro-furan-2-ylmethyl ester (172342-53-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 27 percent / pyridine / 4 h / 0 °C

2: 88 percent / pyridine, CrO₃, Ac₂O / CH₂Cl₂ / 0.25 h / Ambient temperature

3: 71 percent / Zn, TiCl₄ / CH₂Cl₂; tetrahydrofuran / 1.) 0 deg C, 15 min, 2.) r.t., 45 min

With pyridine; chromium(VI) oxide; acetic anhydride; titanium tetrachloride; zinc; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo00127a041

upstream raw materials:

Methyl 2-deoxy-5-O-(4-phenylbenzoyl)-β-D-glyceropentofuranosid-3-ulose

1,1-dibromomethane

methyl 2-deoxy-5-O-(4-phenylbenzoyl)-β-D-erythro-pentofuranoside

4-biphenyl-carboxylic acid chloride

Downstream raw materials:

Methyl 3-C-(adenin-9-ylmethyl)-2-deoxy-5-O-(4-phenylbenzoyl)-β-D-erythro-pentofuranoside

Methyl 2-deoxy-5-O-(4-phenylbenzoyl)-3-C-((thymin-1-yl)methyl)-β-D-erythro-pentofuranoside

Biphenyl-4-carboxylic acid (2R,3R,5R)-3-hydroxy-3-hydroxymethyl-5-methoxy-tetrahydro-furan-2-ylmethyl ester