Benzoic acid (3R,4R,5R)-4-benzyloxy-2-methoxy-5-methyl-tetrahydro-furan-3-yl ester

Base Information

• Chemical Name: Benzoic acid (3R,4R,5R)-4-benzyloxy-2-methoxy-5-methyl-tetrahydro-furan-3-yl ester
• CAS No.: 162210-58-4
• Molecular Formula: C₂₀H₂₂O₅
• Molecular Weight: 342.392
• Mol file: 162210-58-4.mol

Synonyms:Benzoic acid (3R,4R,5R)-4-benzyloxy-2-methoxy-5-methyl-tetrahydro-furan-3-yl ester

Chemical Property of Benzoic acid (3R,4R,5R)-4-benzyloxy-2-methoxy-5-methyl-tetrahydro-furan-3-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzoic acid (3R,4R,5R)-4-benzyloxy-2-methoxy-5-methyl-tetrahydro-furan-3-yl ester

There total 1 articles about Benzoic acid (3R,4R,5R)-4-benzyloxy-2-methoxy-5-methyl-tetrahydro-furan-3-yl 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: 95.0%

benzoyl chloride (98-88-4) + (3R,4S,5R)-4-Benzyloxy-2-methoxy-5-methyl-tetrahydro-furan-3-ol → Benzoic acid (3R,4R,5R)-4-benzyloxy-2-methoxy-5-methyl-tetrahydro-furan-3-yl ester (162210-58-4)

Guidance literature:

With TEA; In dichloromethane; for 10h; Ambient temperature;

DOI:10.1016/0040-4039(94)80021-9

Reference yield: 87.0%

Benzoic acid (3R,4R,5R)-4-benzyloxy-2-methoxy-5-methyl-tetrahydro-furan-3-yl ester (162210-58-4) + ethanethiol (75-08-1) → Benzoic acid (1R,2R,3R)-2-benzyloxy-1-(bis-ethylsulfanyl-methyl)-3-hydroxy-butyl ester

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at -20 ℃; for 3h;

DOI:10.1016/0040-4039(94)80021-9

Reference yield:

Benzoic acid (3R,4R,5R)-4-benzyloxy-2-methoxy-5-methyl-tetrahydro-furan-3-yl ester (162210-58-4) → (E)-(3R,6S,7R)-6-Benzyloxy-3-[(R)-2-(2-isobutyl-[1,3]dioxolan-2-yl)-1-methyl-ethyl]-7-methoxymethoxy-oct-4-enoic acid ethyl ester (162210-51-7)

Guidance literature:

Multi-step reaction with 6 steps

1: 87 percent / BF₃*Et₂O / CH₂Cl₂ / 3 h / -20 °C

2: 92 percent / Hunig's base / CH₂Cl₂ / 0 deg C, 1 h and room t., 15 h

3: 68 percent / I₂, NaHCO₃ / acetone; H₂O / 1 h / -20 °C

4: 62 percent / n-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide / -78 deg C, 3 h, room t., 1 h

5: 95 percent / K₂CO₃ / methanol / 5 h / 40 °C

6: 93 percent / EtCOOH / 4 h / 120 °C

With n-butyllithium; boron trifluoride diethyl etherate; iodine; sodium hydrogencarbonate; potassium carbonate; N-ethyl-N,N-diisopropylamine; propionic acid; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; water; acetone;

DOI:10.1016/0040-4039(94)80021-9

upstream raw materials:

benzoyl chloride

Downstream raw materials:

(-)-Reiswigin A

Benzoic acid (1R,2R,3R)-2-benzyloxy-1-formyl-3-methoxymethoxy-butyl ester

(Z)-(2R,3S,4S,7R)-3-Benzyloxy-8-(2-isobutyl-[1,3]dioxolan-2-yl)-2-methoxymethoxy-7-methyl-oct-5-en-4-ol

Benzoic acid (1R,2R,3R)-2-benzyloxy-1-(bis-ethylsulfanyl-methyl)-3-methoxymethoxy-butyl ester