(1R,2S,3S,4S)-1,4-di(benzoyloxy)-2-hydroxymethyl-3-(2-methoxycarbonylethyl)cyclopentane

Base Information

Chemical Name:(1R,2S,3S,4S)-1,4-di(benzoyloxy)-2-hydroxymethyl-3-(2-methoxycarbonylethyl)cyclopentane
CAS No.:358395-64-9
Molecular Formula:C₂₄H₂₆O₇
Molecular Weight:426.466
Hs Code.:

Synonyms:(1R,2S,3S,4S)-1,4-di(benzoyloxy)-2-hydroxymethyl-3-(2-methoxycarbonylethyl)cyclopentane

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Chemical Property of (1R,2S,3S,4S)-1,4-di(benzoyloxy)-2-hydroxymethyl-3-(2-methoxycarbonylethyl)cyclopentane

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Technology Process of (1R,2S,3S,4S)-1,4-di(benzoyloxy)-2-hydroxymethyl-3-(2-methoxycarbonylethyl)cyclopentane

There total 10 articles about (1R,2S,3S,4S)-1,4-di(benzoyloxy)-2-hydroxymethyl-3-(2-methoxycarbonylethyl)cyclopentane 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: 74.0%

: 358395-57-0
(1R,2S,3S,4S)-1,4-bis-O-(benzoyl)-2-(tert-butyldiphenylsilyloxymethyl)-3-(methoxycarbonylethyl)cyclopentane-1,4-diol

: 358395-64-9
(1R,2S,3S,4S)-1,4-di(benzoyloxy)-2-hydroxymethyl-3-(2-methoxycarbonylethyl)cyclopentane

Guidance literature:: With hydrogenchloride; methanol; In diethyl ether;
DOI:10.1016/S0040-4039(01)00754-7

Reference yield:

: 358395-59-2
(2S,4R,5R)-6-(tert-butyldiphenylsilyloxy)-1,1-diethylthio-5-iodohexane-2,4-diol

: 358395-64-9
(1R,2S,3S,4S)-1,4-di(benzoyloxy)-2-hydroxymethyl-3-(2-methoxycarbonylethyl)cyclopentane

Guidance literature:: Multi-step reaction with 7 steps

1: 88 percent / pyridine / 20 °C

2: 100 percent / HgO; HgCl₂ / acetone; H₂O / Heating

3: 74 percent / KHMDS / tetrahydrofuran / 1 h / -80 - 20 °C

4: Jones reagent / acetone / 2 h / -10 - 20 °C

5: 401 mg / diethyl ether

6: 72 percent / Bu₃SnH; BEt₃; O₂ / p-xylene / 0.67 h / 20 °C

7: 68 percent / HCl / diethyl ether; methanol / 20 h / 20 °C

With hydrogenchloride; jones reagent; triethyl borane; oxygen; tri-n-butyl-tin hydride; potassium hexamethylsilazane; mercury dichloride; mercury(II) oxide; In tetrahydrofuran; pyridine; methanol; diethyl ether; para-xylene; water; acetone;
DOI:10.1016/S0040-4020(03)00258-8

Reference yield:

: 358395-61-6
(2S,4R,5R)-6-(tert-butyldiphenylsilyloxy)-2,4-di(benzoyloxy)-5-iodohexanal

: 358395-64-9
(1R,2S,3S,4S)-1,4-di(benzoyloxy)-2-hydroxymethyl-3-(2-methoxycarbonylethyl)cyclopentane

Guidance literature:: Multi-step reaction with 5 steps

1: 74 percent / KHMDS / tetrahydrofuran / 1 h / -80 - 20 °C

2: Jones reagent / acetone / 2 h / -10 - 20 °C

3: 401 mg / diethyl ether

4: 72 percent / Bu₃SnH; BEt₃; O₂ / p-xylene / 0.67 h / 20 °C

5: 68 percent / HCl / diethyl ether; methanol / 20 h / 20 °C

With hydrogenchloride; jones reagent; triethyl borane; oxygen; tri-n-butyl-tin hydride; potassium hexamethylsilazane; In tetrahydrofuran; methanol; diethyl ether; para-xylene; acetone;
DOI:10.1016/S0040-4020(03)00258-8