(4aR)-4,4a-Anhydro-5-O-benzyl-4a-carba-1-O-(triisopropylsilyl)-2,3-O-isopropylidene-β-D-ribofuranose

Base Information

Chemical Name:(4aR)-4,4a-Anhydro-5-O-benzyl-4a-carba-1-O-(triisopropylsilyl)-2,3-O-isopropylidene-β-D-ribofuranose
CAS No.:243462-55-7
Molecular Formula:C₂₅H₄₀O₅Si
Molecular Weight:448.675
Hs Code.:

Synonyms:(4aR)-4,4a-Anhydro-5-O-benzyl-4a-carba-1-O-(triisopropylsilyl)-2,3-O-isopropylidene-β-D-ribofuranose

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (4aR)-4,4a-Anhydro-5-O-benzyl-4a-carba-1-O-(triisopropylsilyl)-2,3-O-isopropylidene-β-D-ribofuranose

Chemical Property:

Purity/Quality:: 98% ^*data from raw suppliers

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Technology Process of (4aR)-4,4a-Anhydro-5-O-benzyl-4a-carba-1-O-(triisopropylsilyl)-2,3-O-isopropylidene-β-D-ribofuranose

There total 3 articles about (4aR)-4,4a-Anhydro-5-O-benzyl-4a-carba-1-O-(triisopropylsilyl)-2,3-O-isopropylidene-β-D-ribofuranose 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: 88.3%

: 13154-24-0
triisopropylsilyl chloride

: 247909-16-6
(4aR)-4,4a-Anhydro-5-O-benzyl-4a-carba-2,3-O-isopropylidene-β-D-ribofuranose

: 243462-55-7
(4aR)-4,4a-Anhydro-5-O-benzyl-4a-carba-1-O-(triisopropylsilyl)-2,3-O-isopropylidene-β-D-ribofuranose

Guidance literature:: With pyridine; dmap; at 25 ℃; for 6h;
DOI:10.1515/znb-1999-0816

Reference yield:

: 89291-76-9
(1S,4R,5S)-(-)-3-<(benzyloxy)methyl>-4,5-O-isopropylidene-2-cyclopenten-1-ol

: 243462-55-7
(4aR)-4,4a-Anhydro-5-O-benzyl-4a-carba-1-O-(triisopropylsilyl)-2,3-O-isopropylidene-β-D-ribofuranose

Guidance literature:: Multi-step reaction with 2 steps

1: 65 percent / m-CPBA / CH₂Cl₂ / 12 h

2: 88.3 percent / pyridine; DMAP / 6 h / 25 °C

With pyridine; dmap; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; 1: Epoxidation / 2: Etherification;
DOI:10.1515/znb-1999-0816

Reference yield:

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

: 243462-55-7
(4aR)-4,4a-Anhydro-5-O-benzyl-4a-carba-1-O-(triisopropylsilyl)-2,3-O-isopropylidene-β-D-ribofuranose

Guidance literature:: Multi-step reaction with 3 steps

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

2: 65 percent / m-CPBA / CH₂Cl₂ / 12 h

3: 88.3 percent / pyridine; DMAP / 6 h / 25 °C

With pyridine; dmap; sodium tetrahydroborate; cerium(III) chloride; 3-chloro-benzenecarboperoxoic acid; In methanol; dichloromethane; 1: Reduction / 2: Epoxidation / 3: Etherification;
DOI:10.1515/znb-1999-0816