Propionic acid (R)-5-((3aR,5R,6S,6aR)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-tetrahydro-furan-2-ylmethyl ester

Base Information

• Chemical Name: Propionic acid (R)-5-((3aR,5R,6S,6aR)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-tetrahydro-furan-2-ylmethyl ester
• CAS No.: 221015-13-0
• Molecular Formula: C₂₂H₃₀O₇
• Molecular Weight: 406.476
• Mol file: 221015-13-0.mol

Synonyms:

Chemical Property of Propionic acid (R)-5-((3aR,5R,6S,6aR)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-tetrahydro-furan-2-ylmethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Propionic acid (R)-5-((3aR,5R,6S,6aR)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-tetrahydro-furan-2-ylmethyl ester

There total 4 articles about Propionic acid (R)-5-((3aR,5R,6S,6aR)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-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:

2',5-Anhydro-3-O-benzyl-6-deoxy-5-C-((2'R,S)-2'-hydroxy-3'-iodopropyl)-1,2-O-isopropylidene-α-D-glucofuranose (221015-12-9) → (R)-5-((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-5-hydroxy-pentan-2-one + Propionic acid (R)-5-((3aR,5R,6S,6aR)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-tetrahydro-furan-2-ylmethyl ester (221015-13-0)

Guidance literature:

With cesium propionate; In N,N-dimethyl-formamide; at 60 ℃; Yield given. Yields of byproduct given;

DOI:10.1055/s-1999-3392

Reference yield:

3-O-benzyl-1,2-O-isopropylidene-1,5-D-xylo-dialdofuranose (23558-05-6) → Propionic acid (R)-5-((3aR,5R,6S,6aR)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-tetrahydro-furan-2-ylmethyl ester (221015-13-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) Mg / 1.) Et₂O, reflux, 1 h, 2.) Et₂O, 1 h

2: 58 percent / I₂, NaHCO₃ / dimethylformamide / 1 h / 20 °C

3: 1.) Cs₂CO₃ / 1.) DMF, 30 min, 2.) DMF, 60 deg C, overnight

With iodine; sodium hydrogencarbonate; caesium carbonate; magnesium; In N,N-dimethyl-formamide;

DOI:10.1055/s-1999-3392

Reference yield:

1(1R)-1-((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)pent-4-en-1-ol (209849-11-6) → Propionic acid (R)-5-((3aR,5R,6S,6aR)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-tetrahydro-furan-2-ylmethyl ester (221015-13-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 58 percent / I₂, NaHCO₃ / dimethylformamide / 1 h / 20 °C

2: 1.) Cs₂CO₃ / 1.) DMF, 30 min, 2.) DMF, 60 deg C, overnight

With iodine; sodium hydrogencarbonate; caesium carbonate; In N,N-dimethyl-formamide;

DOI:10.1055/s-1999-3392

upstream raw materials:

propionic acid

2',5-Anhydro-3-O-benzyl-6-deoxy-5-C-((2'R,S)-2'-hydroxy-3'-iodopropyl)-1,2-O-isopropylidene-α-D-glucofuranose

3-O-benzyl-1,2-O-isopropylidene-1,5-D-xylo-dialdofuranose

1(1R)-1-((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)pent-4-en-1-ol