(E)-3-((2R,3R,4R,5S)-3-Benzyloxy-4,5-dihydroxy-tetrahydro-furan-2-yl)-acrylic acid ethyl ester

Base Information

• Chemical Name: (E)-3-((2R,3R,4R,5S)-3-Benzyloxy-4,5-dihydroxy-tetrahydro-furan-2-yl)-acrylic acid ethyl ester
• CAS No.: 247144-48-5
• Molecular Formula: C₁₆H₂₀O₆
• Molecular Weight: 308.331
• Mol file: 247144-48-5.mol

Synonyms:(E)-3-((2R,3R,4R,5S)-3-Benzyloxy-4,5-dihydroxy-tetrahydro-furan-2-yl)-acrylic acid ethyl ester

Chemical Property of (E)-3-((2R,3R,4R,5S)-3-Benzyloxy-4,5-dihydroxy-tetrahydro-furan-2-yl)-acrylic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-3-((2R,3R,4R,5S)-3-Benzyloxy-4,5-dihydroxy-tetrahydro-furan-2-yl)-acrylic acid ethyl ester

There total 1 articles about (E)-3-((2R,3R,4R,5S)-3-Benzyloxy-4,5-dihydroxy-tetrahydro-furan-2-yl)-acrylic acid ethyl 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:

ethyl (E)-[3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-gluco]-heptofuran-5-en-uronate (108788-49-4) → (E)-3-((2R,3R,4R,5S)-3-Benzyloxy-4,5-dihydroxy-tetrahydro-furan-2-yl)-acrylic acid ethyl ester (247144-48-5)

Guidance literature:

With trifluoroacetic acid; In water; at 0 - 25 ℃; for 3h;

DOI:10.1016/j.tetlet.2004.09.053

Reference yield: 83.0%

(E)-3-((2R,3R,4R,5S)-3-Benzyloxy-4,5-dihydroxy-tetrahydro-furan-2-yl)-acrylic acid ethyl ester (247144-48-5) → (E)-(4R,5S)-5-Benzyloxy-4-formyloxy-6-oxo-hex-2-enoic acid ethyl ester

Guidance literature:

With sodium periodate; In water; acetone; at 0 - 25 ℃; for 0.666667h;

DOI:10.1016/j.tetlet.2004.09.053

Reference yield:

(E)-3-((2R,3R,4R,5S)-3-Benzyloxy-4,5-dihydroxy-tetrahydro-furan-2-yl)-acrylic acid ethyl ester (247144-48-5) → (3aS,6R,6aR)-4-Benzyl-6-benzyloxy-hexahydro-furo[3,2-b]pyrrol-2-one (800407-08-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 83 percent / NaIO₄ / acetone; H₂O / 0.67 h / 0 - 25 °C

2.1: AcOH / methanol / 1.5 h / -20 °C

2.2: 47 percent / NaCNBH₃ / methanol / -20 - 20 °C

With sodium periodate; acetic acid; In methanol; water; acetone;

DOI:10.1016/j.tetlet.2004.09.053

upstream raw materials:

ethyl (E)-[3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-gluco]-heptofuran-5-en-uronate

Downstream raw materials:

1,4,5-trideoxy-1,4-imino-L-xylo-hexitol

1,4,5-trideoxy-1,4-imino-D-arabino-hexitol

(3aS,6R,6aR)-4-Benzyl-6-benzyloxy-hexahydro-furo[3,2-b]pyrrol-2-one

(2R,3R,4R)-1-Benzyl-4-benzyloxy-2-(2-hydroxy-ethyl)-pyrrolidin-3-ol