<3S-(3α,4β,5α)>-5-(Benzyloxy)-1-(hydroxymethyl)-3,4-bis(methoxymethoxy)-1-cyclopentene

Base Information

Chemical Name:<3S-(3α,4β,5α)>-5-(Benzyloxy)-1-(hydroxymethyl)-3,4-bis(methoxymethoxy)-1-cyclopentene
CAS No.:144811-26-7
Molecular Formula:C₁₇H₂₄O₆
Molecular Weight:324.374
Hs Code.:

Synonyms:<3S-(3α,4β,5α)>-5-(Benzyloxy)-1-(hydroxymethyl)-3,4-bis(methoxymethoxy)-1-cyclopentene

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Chemical Property of <3S-(3α,4β,5α)>-5-(Benzyloxy)-1-(hydroxymethyl)-3,4-bis(methoxymethoxy)-1-cyclopentene

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Technology Process of <3S-(3α,4β,5α)>-5-(Benzyloxy)-1-(hydroxymethyl)-3,4-bis(methoxymethoxy)-1-cyclopentene

There total 11 articles about <3S-(3α,4β,5α)>-5-(Benzyloxy)-1-(hydroxymethyl)-3,4-bis(methoxymethoxy)-1-cyclopentene 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:

: 144811-25-6
((3S,4R,5R)-5-Benzyloxy-3,4-bis-methoxymethoxy-cyclopent-1-enylmethoxy)-tert-butyl-dimethyl-silane

: 144811-26-7
<3S-(3α,4β,5α)>-5-(Benzyloxy)-1-(hydroxymethyl)-3,4-bis(methoxymethoxy)-1-cyclopentene

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 ℃; for 1h; Yield given;
DOI:10.1021/ja00051a051

Reference yield:

: 144811-22-3
(4S-trans)-2-(Hydroxymethyl)-4,5-bis(methoxymethoxy)-2-cyclopenten-1-one

: 144811-26-7
<3S-(3α,4β,5α)>-5-(Benzyloxy)-1-(hydroxymethyl)-3,4-bis(methoxymethoxy)-1-cyclopentene

Guidance literature:: Multi-step reaction with 4 steps

1: 88 percent / imidazole / dimethylformamide / 1.) 0 deg C, 10 min, 2.) 25 deg C, 16 h

2: 53 percent / CeCl₃*7H₂O, NaBH₄ / methanol / 1.) 0 deg C, 30 min, 2.) 25 deg C, 2 h

3: 75 percent / NaH / dimethylformamide / 1 h / 0 °C

4: TBAF / tetrahydrofuran / 1 h / 0 °C

With 1H-imidazole; sodium tetrahydroborate; cerium(III) chloride; tetrabutyl ammonium fluoride; sodium hydride; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;
DOI:10.1021/jo00083a023

Reference yield:

: 144811-23-4
(4S-trans)-2-<<(tert-Butyldimethylsilyl)oxy>methyl>-4,5-bis(methoxymethoxy)-2-cyclopenten-1-one

: 144811-26-7
<3S-(3α,4β,5α)>-5-(Benzyloxy)-1-(hydroxymethyl)-3,4-bis(methoxymethoxy)-1-cyclopentene

Guidance literature:: Multi-step reaction with 3 steps

1: 53 percent / CeCl₃*7H₂O, NaBH₄ / methanol / 1.) 0 deg C, 30 min, 2.) 25 deg C, 2 h

2: 75 percent / NaH / dimethylformamide / 1 h / 0 °C

3: TBAF / tetrahydrofuran / 1 h / 0 °C

With sodium tetrahydroborate; cerium(III) chloride; tetrabutyl ammonium fluoride; sodium hydride; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;
DOI:10.1021/jo00083a023