(R)-(5-benzyloxymethyl-furan-2-yl)hydroxyacetic acid butyl ester

Base Information

• Chemical Name: (R)-(5-benzyloxymethyl-furan-2-yl)hydroxyacetic acid butyl ester
• CAS No.: 100638-89-9
• Molecular Formula: C₁₈H₂₂O₅
• Molecular Weight: 318.37
• Mol file: 100638-89-9.mol

Synonyms:(R)-(5-benzyloxymethyl-furan-2-yl)hydroxyacetic acid butyl ester

Chemical Property of (R)-(5-benzyloxymethyl-furan-2-yl)hydroxyacetic acid butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-(5-benzyloxymethyl-furan-2-yl)hydroxyacetic acid butyl ester

There total 2 articles about (R)-(5-benzyloxymethyl-furan-2-yl)hydroxyacetic acid butyl 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: 90.0%

2-benzyloxymethylfuran (16361-14-1) + butyl glyoxalate (6295-06-3) → (R)-(5-benzyloxymethyl-furan-2-yl)hydroxyacetic acid butyl ester (100638-89-9)

Guidance literature:

butyl glyoxalate; With titanium(IV) isopropylate; (R)-6,6'-dibromo-1,1'-binaphth-2-ol; In toluene; at 0 ℃;

2-benzyloxymethylfuran; In toluene; at 0 - 20 ℃; for 20h; optical yield given as %ee; enantioselective reaction;

DOI:10.1021/ol800927w

Reference yield: 55.0%

2-benzyloxymethylfuran (16361-14-1) + butyl glyoxalate (6295-06-3) → butyl 2-(5-benzyloxymethyl-2-furyl)glycolate (100638-89-9,100638-90-2)

Guidance literature:

With toluene-4-sulfonic acid; In benzene; for 12h; Ambient temperature;

DOI:10.1016/S0008-6215(00)90756-0

Reference yield:

butyl 2-(5-benzyloxymethyl-2-furyl)glycolate (100638-89-9,100638-90-2) → 1,7-di-O-benzyl-3,4-dideoxy-α-DL-hept-3-en-2-ulopyranos-5-ulose (100638-97-9,100638-98-0)

Guidance literature:

Multi-step reaction with 6 steps

1: toluene-p-sulphonic acid / 0.5 h / 0 °C

2: 99 percent / lithium aluminium hydride / diethyl ether / 0.25 h

3: 93 percent / NaOH / dimethylsulfoxide / 12 h

4: 100 percent / toluene-p-sulphonic acid / methanol / 4 h / Ambient temperature

5: 94 percent / Br₂ / diethyl ether / 0.5 h / -45 - -35 °C

6: aq. 1percent H₂SO₄ / acetone / 2 h / Ambient temperature

With sodium hydroxide; lithium aluminium tetrahydride; sulfuric acid; bromine; toluene-4-sulfonic acid; In methanol; diethyl ether; dimethyl sulfoxide; acetone;

DOI:10.1016/S0008-6215(00)90756-0

upstream raw materials:

2-benzyloxymethylfuran

butyl glyoxalate

Downstream raw materials:

butyl 2-(5-benzyloxymethyl-2-furyl)-O-(tetrahydropyran-2-yl)glycolate

2-benzyloxymethyl-5-<2-hydroxy-1-(tetrahydropyran-2-yloxy)ethyl>furan

2-benzyloxymethyl-5-(2-benzyloxy-1-hydroxyethyl)furan

2-(2-benzyloxy-1-hydroxyethyl)-5-benzyloxymethyl-2,5-dimethoxy-2,5-dihydrofuran