(-)-(1R,2R,3S,5R)-3-(benzyloxy)-5-(hydroxymethyl)-4-methylenecyclopentane-1,2-diol

Base Information

Chemical Name:(-)-(1R,2R,3S,5R)-3-(benzyloxy)-5-(hydroxymethyl)-4-methylenecyclopentane-1,2-diol
CAS No.:1307273-60-4
Molecular Formula:C₁₄H₁₈O₄
Molecular Weight:250.295
Hs Code.:

Synonyms:(-)-(1R,2R,3S,5R)-3-(benzyloxy)-5-(hydroxymethyl)-4-methylenecyclopentane-1,2-diol

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Chemical Property of (-)-(1R,2R,3S,5R)-3-(benzyloxy)-5-(hydroxymethyl)-4-methylenecyclopentane-1,2-diol

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Technology Process of (-)-(1R,2R,3S,5R)-3-(benzyloxy)-5-(hydroxymethyl)-4-methylenecyclopentane-1,2-diol

There total 4 articles about (-)-(1R,2R,3S,5R)-3-(benzyloxy)-5-(hydroxymethyl)-4-methylenecyclopentane-1,2-diol 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:

: 1307273-58-0
(3aS,4S,6R,6aR)-6-(tert-butoxymethyl)-2,2-dimethyl-5-methylenetetrahydro-3aH-cyclopenta[d][1,3]-dioxol-4-ol

: 1307273-60-4
(-)-(1R,2R,3S,5R)-3-(benzyloxy)-5-(hydroxymethyl)-4-methylenecyclopentane-1,2-diol

Guidance literature:: Multi-step reaction with 2 steps

1.1: sodium hydride / tetrahydrofuran / 0.25 h / 20 °C

1.2: 3.5 h / 40 °C

2.1: hydrogenchloride; water / methanol / 3.5 h / Reflux

With hydrogenchloride; water; sodium hydride; In tetrahydrofuran; methanol;

Reference yield:

: 223596-25-6
(3aR,6R,6aR)-6-(tert-butoxymethyl)-2,2-dimethyltetrahydro-4H-cyclopenta[d][1,3]dioxol-4-one

: 1307273-60-4
(-)-(1R,2R,3S,5R)-3-(benzyloxy)-5-(hydroxymethyl)-4-methylenecyclopentane-1,2-diol

Guidance literature:: Multi-step reaction with 4 steps

1.1: lithium diisopropyl amide / tetrahydrofuran / 3 h / -78 °C

1.2: -78 - 20 °C

1.3: 4 h / 20 °C

2.1: cerium(III) chloride heptahydrate / methanol / 0.17 h / 20 °C

2.2: 0.33 h / -78 °C

3.1: sodium hydride / tetrahydrofuran / 0.25 h / 20 °C

3.2: 3.5 h / 40 °C

4.1: hydrogenchloride; water / methanol / 3.5 h / Reflux

With hydrogenchloride; cerium(III) chloride heptahydrate; water; sodium hydride; lithium diisopropyl amide; In tetrahydrofuran; methanol; 1.3: Hofmann Degradation;

Reference yield:

: 1307273-57-9
(3R,6R,6aR)-6-(tert-butoxymethyl)-2,2-dimethyl-5-methylenedihydro-3aH-cyclopenta[d][1,3]-dioxol-4-(5H)one

: 1307273-60-4
(-)-(1R,2R,3S,5R)-3-(benzyloxy)-5-(hydroxymethyl)-4-methylenecyclopentane-1,2-diol

Guidance literature:: Multi-step reaction with 3 steps

1.1: cerium(III) chloride heptahydrate / methanol / 0.17 h / 20 °C

1.2: 0.33 h / -78 °C

2.1: sodium hydride / tetrahydrofuran / 0.25 h / 20 °C

2.2: 3.5 h / 40 °C

3.1: hydrogenchloride; water / methanol / 3.5 h / Reflux

With hydrogenchloride; cerium(III) chloride heptahydrate; water; sodium hydride; In tetrahydrofuran; methanol;