(+/-)-4β-(tert-Butyldiphenylsiloxymethyl)-2α,3α-(isopropylidenedioxy)(1-²H)cyclopentan-1α-ol

Base Information

• Chemical Name: (+/-)-4β-(tert-Butyldiphenylsiloxymethyl)-2α,3α-(isopropylidenedioxy)(1-²H)cyclopentan-1α-ol
• CAS No.: 144874-61-3
• Molecular Formula: C₂₅H₃₄O₄Si
• Molecular Weight: 427.62

Synonyms:(+/-)-4β-(tert-Butyldiphenylsiloxymethyl)-2α,3α-(isopropylidenedioxy)(1-²H)cyclopentan-1α-ol

Chemical Property of (+/-)-4β-(tert-Butyldiphenylsiloxymethyl)-2α,3α-(isopropylidenedioxy)(1-²H)cyclopentan-1α-ol

Chemical Property:

Purity/Quality:

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Technology Process of (+/-)-4β-(tert-Butyldiphenylsiloxymethyl)-2α,3α-(isopropylidenedioxy)(1-²H)cyclopentan-1α-ol

There total 7 articles about (+/-)-4β-(tert-Butyldiphenylsiloxymethyl)-2α,3α-(isopropylidenedioxy)(1-²H)cyclopentan-1α-ol 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: 89.0%

(3aRS,6RS,6aRS)-6-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethyldihydro-3aH-cyclopenta[d][1,3]dioxol-4(5H)-one (144874-60-2) → (+/-)-4β-(tert-Butyldiphenylsiloxymethyl)-2α,3α-(isopropylidenedioxy)(1-2H)cyclopentan-1α-ol (144874-61-3)

Guidance literature:

With sodium borodeuteride; In ethanol; at 0 ℃; for 1h;

Reference yield:

cyclopenta-1,3-diene (542-92-7,25568-84-7,7313-32-8) → (+/-)-4β-(tert-Butyldiphenylsiloxymethyl)-2α,3α-(isopropylidenedioxy)(1-2H)cyclopentan-1α-ol (144874-61-3)

Guidance literature:

Multi-step reaction with 6 steps

1: 2.) imidazole, 4-(dimethylamino)pyridine / 2.) dichloromethane, 0 deg C, 3 h

2: 84 percent / N-Methylmorpholine N-oxide / osmium tetraoxide / acetone; H₂O; butan-1-ol / 15 h / Ambient temperature

3: 81 percent / p-toluenesulfonic acid / 3 h / Ambient temperature

4: 250 mg / imidazole, 4-(dimethylamino)pyridine / CH₂Cl₂ / 0.5 h / 0 °C

5: 2.33 g / pyridinium chlorochromate, 4 Angstroem molecular sieves / CH₂Cl₂ / 1 h / Ambient temperature

6: 89 percent / NaBD₄ / aq. ethanol / 1 h / 0 °C

With 1H-imidazole; dmap; sodium borodeuteride; 4 A molecular sieve; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; pyridinium chlorochromate; osmium(VIII) oxide; In ethanol; dichloromethane; water; acetone; butan-1-ol;

Reference yield:

(+/-)-4β-(tert-Butyldimethylsiloxymethyl)cyclopent-2-en-1β-ol (137760-85-1,144938-70-5) → (+/-)-4β-(tert-Butyldiphenylsiloxymethyl)-2α,3α-(isopropylidenedioxy)(1-2H)cyclopentan-1α-ol (144874-61-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 84 percent / N-Methylmorpholine N-oxide / osmium tetraoxide / acetone; H₂O; butan-1-ol / 15 h / Ambient temperature

2: 81 percent / p-toluenesulfonic acid / 3 h / Ambient temperature

3: 250 mg / imidazole, 4-(dimethylamino)pyridine / CH₂Cl₂ / 0.5 h / 0 °C

4: 2.33 g / pyridinium chlorochromate, 4 Angstroem molecular sieves / CH₂Cl₂ / 1 h / Ambient temperature

5: 89 percent / NaBD₄ / aq. ethanol / 1 h / 0 °C

With 1H-imidazole; dmap; sodium borodeuteride; 4 A molecular sieve; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; pyridinium chlorochromate; osmium(VIII) oxide; In ethanol; dichloromethane; water; acetone; butan-1-ol;

upstream raw materials:

(3aRS,6RS,6aRS)-6-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethyldihydro-3aH-cyclopenta[d][1,3]dioxol-4(5H)-one

cyclopenta-1,3-diene

(+/-)-4β-(tert-Butyldimethylsiloxymethyl)cyclopent-2-en-1β-ol

(+/-)-4β-(tert-Butyldimethylsiloxymethyl)cyclopentane-1β,2α,3α-triol

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