(3aR,4S,6aR)-6-(Benzyloxymethyl)-4-(triisopropylsilyloxy)-2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[d][1,3]dioxol

Base Information

• Chemical Name: (3aR,4S,6aR)-6-(Benzyloxymethyl)-4-(triisopropylsilyloxy)-2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[d][1,3]dioxol
• CAS No.: 246137-20-2
• Molecular Formula: C₂₅H₄₀O₄Si
• Molecular Weight: 432.676

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

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

Chemical Property:

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

There total 2 articles about (3aR,4S,6aR)-6-(Benzyloxymethyl)-4-(triisopropylsilyloxy)-2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[d][1,3]dioxol 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: 99.0%

triisopropylsilyl chloride (13154-24-0) + (1S,4R,5S)-(-)-3-<(benzyloxy)methyl>-4,5-O-isopropylidene-2-cyclopenten-1-ol (89291-76-9) → (3aR,4S,6aR)-6-(Benzyloxymethyl)-4-(triisopropylsilyloxy)-2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[d][1,3]dioxol (246137-20-2)

Guidance literature:

With pyridine; dmap; at 25 ℃; for 24h;

DOI:10.1515/znb-1999-0816

Reference yield:

(3aR,6aR)-6-Benzyloxymethyl-2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[d][1,3]dioxol-4-one (117307-62-7,89291-75-8) → (3aR,4S,6aR)-6-(Benzyloxymethyl)-4-(triisopropylsilyloxy)-2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[d][1,3]dioxol (246137-20-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 94 percent / NaBH₄; CeCl₃*7H₂O / methanol / -20 - 25 °C

2: 99 percent / pyridine; DMAP / 24 h / 25 °C

With pyridine; dmap; sodium tetrahydroborate; cerium(III) chloride; In methanol; 1: Reduction / 2: Etherification;

DOI:10.1515/znb-1999-0816

Reference yield: 86.0%

(3aR,4S,6aR)-6-(Benzyloxymethyl)-4-(triisopropylsilyloxy)-2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[d][1,3]dioxol (246137-20-2) → (4aS)-4,4a-Anhydro-5-O-benzyl-4a-carba-1-O-(triisopropylsilyl)-2,3-O-isopropylidene-β-L-lyxofuranose (243462-53-5)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 25 ℃; for 12h;

DOI:10.1515/znb-1999-0816

upstream raw materials:

triisopropylsilyl chloride

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

(3aR,6aR)-6-Benzyloxymethyl-2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[d][1,3]dioxol-4-one

Downstream raw materials:

(4aS)-4,4a-Anhydro-5-O-benzyl-4a-carba-1-O-(triisopropylsilyl)-2,3-O-isopropylidene-β-L-lyxofuranose

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