(3S,4S)-4-Acetoxy-3-benzyloxy-cyclopent-1-enecarboxylic acid methyl ester

Base Information

• Chemical Name: (3S,4S)-4-Acetoxy-3-benzyloxy-cyclopent-1-enecarboxylic acid methyl ester
• CAS No.: 115434-99-6
• Molecular Formula: C₁₆H₁₈O₅
• Molecular Weight: 290.316
• Mol file: 115434-99-6.mol

Synonyms:(3S,4S)-4-Acetoxy-3-benzyloxy-cyclopent-1-enecarboxylic acid methyl ester

Chemical Property of (3S,4S)-4-Acetoxy-3-benzyloxy-cyclopent-1-enecarboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,4S)-4-Acetoxy-3-benzyloxy-cyclopent-1-enecarboxylic acid methyl ester

There total 6 articles about (3S,4S)-4-Acetoxy-3-benzyloxy-cyclopent-1-enecarboxylic acid methyl 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:

dimethyl (2R,3R,4S)-2,4-diacetoxy-3-benzyloxy-1,1-cyclopentanedicarboxylate (115458-54-3) → (3S,4S)-4-Acetoxy-3-benzyloxy-cyclopent-1-enecarboxylic acid methyl ester (115434-99-6)

Guidance literature:

With sodium chloride; In water; dimethyl sulfoxide; 110 - 160 deg C, 2 h; 160 deg C, 4 h;

DOI:10.1246/bcsj.60.3673

Reference yield:

3-O-Benzyl-D-xylose → (3S,4S)-4-Acetoxy-3-benzyloxy-cyclopent-1-enecarboxylic acid methyl ester (115434-99-6)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.) conc. HCl / 1.) -15 min, 30 min; 2.) pyridine, r.t., 13 h

2: mercury(II) chloride, calcium carbonate / acetonitrile; H₂O / 0.5 h / Ambient temperature

3: pyridine; acetic anhydride / 36 h / Ambient temperature

4: sodium borohydride / methanol / 0.5 h / -15 °C

6: NaCl / dimethylsulfoxide; H₂O / 110 - 160 deg C, 2 h; 160 deg C, 4 h

With hydrogenchloride; sodium tetrahydroborate; calcium carbonate; sodium chloride; mercury dichloride; In pyridine; methanol; water; acetic anhydride; dimethyl sulfoxide; acetonitrile;

DOI:10.1246/bcsj.60.3673

Reference yield:

Acetic acid (1R,2S,3R)-3-acetoxy-1-acetoxymethyl-2-benzyloxy-4-oxo-butyl ester (115434-93-0) → (3S,4S)-4-Acetoxy-3-benzyloxy-cyclopent-1-enecarboxylic acid methyl ester (115434-99-6)

Guidance literature:

Multi-step reaction with 4 steps

1: pyridine; acetic anhydride / 36 h / Ambient temperature

2: sodium borohydride / methanol / 0.5 h / -15 °C

4: NaCl / dimethylsulfoxide; H₂O / 110 - 160 deg C, 2 h; 160 deg C, 4 h

With sodium tetrahydroborate; sodium chloride; In pyridine; methanol; water; acetic anhydride; dimethyl sulfoxide;

DOI:10.1246/bcsj.60.3673

upstream raw materials:

dimethyl (2R,3R,4S)-2,4-diacetoxy-3-benzyloxy-1,1-cyclopentanedicarboxylate

Acetic acid (1R,2S,3R)-3-acetoxy-1-acetoxymethyl-2-benzyloxy-4-oxo-butyl ester

2,4,5-tri-O-acetyl-3-O-benzyl-D-xylose diethyl dithioacetal

methyl (4S,5R,6R)-4,6,7-triacetoxy-5-benzyloxy-2-(methoxycarbonyl)heptanoate

Downstream raw materials:

(3S,4S)-3-benzyloxy-4-hydroxy-1-cyclopentene-1-methanol

(S)-2-Benzyloxy-4-(tert-butyl-diphenyl-silanyloxymethyl)-cyclopent-3-enone

(3S,4R)-3-benzyloxy-4-hydroxy-1-cyclopentene-1-methanol

(3S,4S)-3-(benzyloxy)-1-<<(t-butyldiphenylsilyl)oxy>methyl>-4-hydroxy-1-cyclopentene