5α-(t-butyldimethylsilyloxy)-2ξ-methoxy-4β--3,3aβ,4,5,6,6aβ-hexahydro-2H-cyclopentafuran

Base Information

• Chemical Name: 5α-(t-butyldimethylsilyloxy)-2ξ-methoxy-4β--3,3aβ,4,5,6,6aβ-hexahydro-2H-cyclopentafuran
• CAS No.: 105394-08-9
• Molecular Formula: C₂₈H₄₀O₆SSi
• Molecular Weight: 532.774

Synonyms:

Chemical Property of 5α-(t-butyldimethylsilyloxy)-2ξ-methoxy-4β--3,3aβ,4,5,6,6aβ-hexahydro-2H-cyclopentafuran

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5α-(t-butyldimethylsilyloxy)-2ξ-methoxy-4β--3,3aβ,4,5,6,6aβ-hexahydro-2H-cyclopentafuran

There total 16 articles about 5α-(t-butyldimethylsilyloxy)-2ξ-methoxy-4β--3,3aβ,4,5,6,6aβ-hexahydro-2H-cyclopentafuran 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,5S,6aR)-4-Phenylsulfanylmethyl-hexahydro-cyclopenta[b]furan-2,5-diol (86021-78-5,105455-57-0,105455-58-1,118919-53-2,118919-54-3) → 2-Benzenesulfonyl-2-[(3aS,5S,6aR)-5-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-hexahydro-cyclopenta[b]furan-4-yl]-1-phenyl-ethanol (105394-08-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 95 percent / BF₃*Et₂O / -20 °C

2: 88 percent / imidazol / dimethylformamide / 40 °C

3: mClPBA / CH₂Cl₂ / -78 °C

With 1H-imidazole; 3-chloro-benzenecarboperoxoic acid; boron trifluoride diethyl etherate; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(01)80897-2

Reference yield:

(3aS,5S,6aR)-5-Hydroxy-4-phenylsulfanylmethyl-hexahydro-cyclopenta[b]furan-2-one (86021-69-4,91739-11-6,118919-52-1) → 2-Benzenesulfonyl-2-[(3aS,5S,6aR)-5-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-hexahydro-cyclopenta[b]furan-4-yl]-1-phenyl-ethanol (105394-08-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 75 percent / DIBAL / CH₂Cl₂ / -78 °C

2: 95 percent / BF₃*Et₂O / -20 °C

3: 88 percent / imidazol / dimethylformamide / 40 °C

4: mClPBA / CH₂Cl₂ / -78 °C

With 1H-imidazole; diisobutylaluminium hydride; 3-chloro-benzenecarboperoxoic acid; boron trifluoride diethyl etherate; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(01)80897-2

Reference yield:

Toluene-4-sulfonic acid (3aS,5S,6aR)-5-hydroxy-2-oxo-hexahydro-cyclopenta[b]furan-4-ylmethyl ester (105394-12-5,118919-51-0) → 2-Benzenesulfonyl-2-[(3aS,5S,6aR)-5-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-hexahydro-cyclopenta[b]furan-4-yl]-1-phenyl-ethanol (105394-08-9)

Guidance literature:

Multi-step reaction with 6 steps

1: 98 percent / t-BuOK / dimethylsulfoxide / 0.5 h / Ambient temperature

2: 75 percent / DIBAL / CH₂Cl₂ / -78 °C

3: 95 percent / BF₃*Et₂O / -20 °C

4: 88 percent / imidazol / dimethylformamide / 40 °C

5: mClPBA / CH₂Cl₂ / -78 °C

With 1H-imidazole; potassium tert-butylate; diisobutylaluminium hydride; 3-chloro-benzenecarboperoxoic acid; boron trifluoride diethyl etherate; In dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(01)80897-2

upstream raw materials:

benzaldehyde

((2S,3aS,5S,6aR)-4-Benzenesulfonylmethyl-2-methoxy-hexahydro-cyclopenta[b]furan-5-yloxy)-tert-butyl-dimethyl-silane

((2R,3aS,5S,6aR)-4-Benzenesulfonylmethyl-2-methoxy-hexahydro-cyclopenta[b]furan-5-yloxy)-tert-butyl-dimethyl-silane

(3aS,5S,6aR)-4-Phenylsulfanylmethyl-hexahydro-cyclopenta[b]furan-2,5-diol

Downstream raw materials:

Benzoic acid 2-benzenesulfonyl-2-[(3aS,4S,5S,6aR)-5-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-hexahydro-cyclopenta[b]furan-4-yl]-1-phenyl-ethyl ester

5α-(t-butyldimethylsilyloxy)-4β-(ethen-2'-phenyl)-2ξ-methoxy-3,3aβ,4,5,6,6aβ-hexahydro-2H-cyclopentafuran

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