3aH-Cyclopenta[b]furan-2,3a,6-triol,hexahydro-,[2S-(2-alpha-,3a-alpha-,6-bta-,6a-alpha-)]-(9CI)

Base Information

• Chemical Name: 3aH-Cyclopenta[b]furan-2,3a,6-triol,hexahydro-,[2S-(2-alpha-,3a-alpha-,6-bta-,6a-alpha-)]-(9CI)
• CAS No.: 149672-39-9
• Molecular Formula: C₇H₁₂O₄
• Molecular Weight: 160.17
• Mol file: 149672-39-9.mol

Synonyms:3aH-Cyclopenta[b]furan-2,3a,6-triol,hexahydro-,[2S-(2-alpha-,3a-alpha-,6-bta-,6a-alpha-)]-(9CI)

Chemical Property of 3aH-Cyclopenta[b]furan-2,3a,6-triol,hexahydro-,[2S-(2-alpha-,3a-alpha-,6-bta-,6a-alpha-)]-(9CI)

Chemical Property:

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3aH-Cyclopenta[b]furan-2,3a,6-triol,hexahydro-,[2S-(2-alpha-,3a-alpha-,6-bta-,6a-alpha-)]-(9CI)

There total 6 articles about 3aH-Cyclopenta[b]furan-2,3a,6-triol,hexahydro-,[2S-(2-alpha-,3a-alpha-,6-bta-,6a-alpha-)]-(9CI) 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:

(3aS,6aS)-2,2-Dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-one (40269-48-5) → (3aS,6R,6aR)-Hexahydro-cyclopenta[b]furan-2,3a,6-triol (149672-39-9)

Guidance literature:

Multi-step reaction with 6 steps

1: 1) NaH / 1) pentane, THF, 0 deg C, 2) THF, r.t., 1 h

2: 1,5,7-triazabicyclo<4.4.0>dec-5-ene / CH₂Cl₂ / 24 h / Ambient temperature

3: 77 percent / 3-chloroperbenzoic acid / CH₂Cl₂ / 22 h / Ambient temperature

4: 1) phosphate buffer, aq. NaOH, 2) LiAlH₄ / 1) r.t., 1.5 h, hog-liver esterase, pH 7.75, 2) Et₂O, reflux, 6 h

5: 66 percent / 1,1,1-triacetoxy-1,1-dihydro-1,2-benziodoxol-3(1H)-one / CH₂Cl₂ / 2 h

6: H₂O, Amberlite IR-120 (H⁽¹⁺⁾ form) / 1.5 h / 55 °C

With sodium hydroxide; lithium aluminium tetrahydride; phosphate buffer; Amberlite IR-120 (H⁽¹⁺⁾ form); water; sodium hydride; Dess-Martin periodane; 3-chloro-benzenecarboperoxoic acid; 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine; In dichloromethane;

DOI:10.1002/hlca.19930760132

Reference yield:

ethyl (E/Z,1'RS,5'SR)-(3',3'-dimethyl-2',4'-dioxabicyclo<3.3.0>oct-6'-ylidene)acetate → (3aS,6R,6aR)-Hexahydro-cyclopenta[b]furan-2,3a,6-triol (149672-39-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 1,5,7-triazabicyclo<4.4.0>dec-5-ene / CH₂Cl₂ / 24 h / Ambient temperature

2: 77 percent / 3-chloroperbenzoic acid / CH₂Cl₂ / 22 h / Ambient temperature

3: 1) phosphate buffer, aq. NaOH, 2) LiAlH₄ / 1) r.t., 1.5 h, hog-liver esterase, pH 7.75, 2) Et₂O, reflux, 6 h

4: 66 percent / 1,1,1-triacetoxy-1,1-dihydro-1,2-benziodoxol-3(1H)-one / CH₂Cl₂ / 2 h

5: H₂O, Amberlite IR-120 (H⁽¹⁺⁾ form) / 1.5 h / 55 °C

With sodium hydroxide; lithium aluminium tetrahydride; phosphate buffer; Amberlite IR-120 (H⁽¹⁺⁾ form); water; Dess-Martin periodane; 3-chloro-benzenecarboperoxoic acid; 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine; In dichloromethane;

DOI:10.1002/hlca.19930760132

Reference yield:

(1'R,5'R,6'S)-(6'-hydroxy-3',3'-dimethyl-2',4'-dioxabicyclo[3.3.0]oct-6'-yl)acetaldehyde → (3aS,6R,6aR)-Hexahydro-cyclopenta[b]furan-2,3a,6-triol (149672-39-9)

Guidance literature:

With Amberlite IR-120 (H⁽¹⁺⁾ form); water; at 55 ℃; for 1.5h;

DOI:10.1002/hlca.19930760132

upstream raw materials:

(3aS,6aS)-2,2-Dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-one

(1R,5R,6S)-6-(2'-hydroxyethyl)-3,3-dimethyl-2,4-dioxabicyclo[3.3.0]octan-6-ol

Refernces