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

Base Information

• Chemical Name: (3S,4R)-3-benzyloxy-4-hydroxy-1-cyclopentene-1-methanol
• CAS No.: 115509-83-6
• Molecular Formula: C₁₃H₁₆O₃
• Molecular Weight: 220.268
• Mol file: 115509-83-6.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 12 articles about (3S,4R)-3-benzyloxy-4-hydroxy-1-cyclopentene-1-methanol 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%

(3S,4R)-3-benzyloxy-1-(t-butyldiphenylsilyloxymethyl)-4-hydroxy-1-cyclopentene (115509-81-4) → (3S,4R)-3-benzyloxy-4-hydroxy-1-cyclopentene-1-methanol (115509-83-6)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 2h; Ambient temperature;

DOI:10.1246/bcsj.60.3673

Reference yield:

3-O-benzyl-1,2-O-isopropylidene-α-D-xylofuranose (34370-91-7,59358-33-7,68354-70-1,70798-12-8,19139-80-1) → (3S,4R)-3-benzyloxy-4-hydroxy-1-cyclopentene-1-methanol (115509-83-6)

Guidance literature:

Multi-step reaction with 12 steps

1: 80percent acetic acid / H₂O / Heating

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

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

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

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

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

8: 75 percent / DIBAL-H / CH₂Cl₂; toluene / -78 °C

9: 73 percent / imidazole / dimethylformamide / Ambient temperature

10: 223 mg / PCC, molecular sieves 4A / CH₂Cl₂ / 0.5 h / Ambient temperature

11: 84 percent / sodium borohydride / methanol / 1 h / 0 °C

12: 90 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / Ambient temperature

With 1H-imidazole; hydrogenchloride; sodium tetrahydroborate; 4 A molecular sieve; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; acetic acid; pyridinium chlorochromate; calcium carbonate; sodium chloride; mercury dichloride; In tetrahydrofuran; pyridine; methanol; dichloromethane; water; acetic anhydride; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1246/bcsj.60.3673

Reference yield:

3-O-Benzyl-D-xylose → (3S,4R)-3-benzyloxy-4-hydroxy-1-cyclopentene-1-methanol (115509-83-6)

Guidance literature:

Multi-step reaction with 11 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

7: 75 percent / DIBAL-H / CH₂Cl₂; toluene / -78 °C

8: 73 percent / imidazole / dimethylformamide / Ambient temperature

9: 223 mg / PCC, molecular sieves 4A / CH₂Cl₂ / 0.5 h / Ambient temperature

10: 84 percent / sodium borohydride / methanol / 1 h / 0 °C

11: 90 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / Ambient temperature

With 1H-imidazole; hydrogenchloride; sodium tetrahydroborate; 4 A molecular sieve; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; pyridinium chlorochromate; calcium carbonate; sodium chloride; mercury dichloride; In tetrahydrofuran; pyridine; methanol; dichloromethane; water; acetic anhydride; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1246/bcsj.60.3673

upstream raw materials:

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

3-O-benzyl-1,2-O-isopropylidene-α-D-xylofuranose

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

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