(3aS,4S,6aS)-4-Benzyloxymethyl-2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[1,3]dioxol-4-ol

Base Information

• Chemical Name: (3aS,4S,6aS)-4-Benzyloxymethyl-2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[1,3]dioxol-4-ol
• CAS No.: 114948-34-4
• Molecular Formula: C₁₆H₂₀O₄
• Molecular Weight: 276.332
• Mol file: 114948-34-4.mol

Synonyms:(3aS,4S,6aS)-4-Benzyloxymethyl-2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[1,3]dioxol-4-ol

Chemical Property of (3aS,4S,6aS)-4-Benzyloxymethyl-2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[1,3]dioxol-4-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3aS,4S,6aS)-4-Benzyloxymethyl-2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[1,3]dioxol-4-ol

There total 8 articles about (3aS,4S,6aS)-4-Benzyloxymethyl-2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[1,3]dioxol-4-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: 86.0%

(benzyloxymethyl)tributylstannane (66222-28-4) + (3aS,6aS)-2,2-dimethyl-3a,6a-dihydro-4H-cyclopenta[d][1,3]dioxol-4-one (104010-72-2) → (3aS,4S,6aS)-4-Benzyloxymethyl-2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[1,3]dioxol-4-ol (114948-34-4)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; at -78 ℃;

DOI:10.1016/S0040-4039(00)95558-8

Reference yield: 79.0%

1-[(4S,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]-1-(benzyloxymethyl)-2-propen-1-ol (681853-97-4) → (3aS,4S,6aS)-4-Benzyloxymethyl-2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[1,3]dioxol-4-ol (114948-34-4) + (1R,4S,5S)-1-(benzyloxymethyl)-2-en-4,5-(O-isopropylidenedioxy)-cyclopentan-1-ol (681853-99-6)

Guidance literature:

tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In dichloromethane; at 20 ℃; for 48h;

DOI:10.1021/jo0356762

Reference yield:

(1R)-(+)-1-[(4R,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]-2-(benzyloxy)ethan-1-ol (97204-83-6) → (3aS,4S,6aS)-4-Benzyloxymethyl-2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[1,3]dioxol-4-ol (114948-34-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 92 percent / oxalyl chloride; triethylamine; DMSO / CH₂Cl₂ / -78 - 20 °C

2: 95 percent / tetrahydrofuran / -78 °C

3: 17 percent / Grubbs catalyst / CH₂Cl₂ / 20 °C

With oxalyl dichloride; dimethyl sulfoxide; triethylamine; Grubbs catalyst first generation; In tetrahydrofuran; dichloromethane; 2: Grignard reaction;

DOI:10.1081/NCN-200061832

upstream raw materials:

(benzyloxymethyl)tributylstannane

(3aS,6aS)-2,2-dimethyl-3a,6a-dihydro-4H-cyclopenta[d][1,3]dioxol-4-one

1-[(4S,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]-1-(benzyloxymethyl)-2-propen-1-ol

5-O-benzyl-2,3-O-isopropylidene-D-ribofuranose

Downstream raw materials:

Acetic acid (3aS,4S,6aS)-4-benzyloxymethyl-2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[1,3]dioxol-4-yl ester

(-)-9-<(1R,4R,5S)-3-<(benzyloxy)methyl>-4,5-O-isopropylidene-2-cyclopenten-1-yl>adenine

(1S,4R,5S)-(-)-3-<(benzyloxy)methyl>-4,5-O-isopropylidene-2-cyclopenten-1-ol

Acetic acid (3aS,4S,6aR)-6-benzyloxymethyl-2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[1,3]dioxol-4-yl ester