[(2R,4S,5S)-5-Iodomethyl-4-(4-methoxy-benzyloxy)-tetrahydro-furan-2-yl]-acetic acid ethyl ester

Base Information

Chemical Name:[(2R,4S,5S)-5-Iodomethyl-4-(4-methoxy-benzyloxy)-tetrahydro-furan-2-yl]-acetic acid ethyl ester
CAS No.:815588-04-6
Molecular Formula:C₁₇H₂₃IO₅
Molecular Weight:434.271
Hs Code.:

Synonyms:[(2R,4S,5S)-5-Iodomethyl-4-(4-methoxy-benzyloxy)-tetrahydro-furan-2-yl]-acetic acid ethyl ester

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Chemical Property of [(2R,4S,5S)-5-Iodomethyl-4-(4-methoxy-benzyloxy)-tetrahydro-furan-2-yl]-acetic acid ethyl ester

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Technology Process of [(2R,4S,5S)-5-Iodomethyl-4-(4-methoxy-benzyloxy)-tetrahydro-furan-2-yl]-acetic acid ethyl ester

There total 1 articles about [(2R,4S,5S)-5-Iodomethyl-4-(4-methoxy-benzyloxy)-tetrahydro-furan-2-yl]-acetic acid ethyl ester 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: 94.0%

: 89238-99-3
O-(4-methoxybenzyl)-trichloroacetimidate

: 112065-93-7
ethyl 2-[(2R,4S,5S)-4-hydroxy-5-(iodomethyl)tetrahydro-2-furanyl]acetate

: 815588-04-6
[(2R,4S,5S)-5-Iodomethyl-4-(4-methoxy-benzyloxy)-tetrahydro-furan-2-yl]-acetic acid ethyl ester

Guidance literature:: With camphor-10-sulfonic acid; In dichloromethane; at 20 ℃; for 20h;
DOI:10.1055/s-2004-831334

Reference yield:

: 815588-04-6
[(2R,4S,5S)-5-Iodomethyl-4-(4-methoxy-benzyloxy)-tetrahydro-furan-2-yl]-acetic acid ethyl ester

: 815588-12-6
(4S,6S)-6,8-Bis-(tert-butyl-dimethyl-silanyloxy)-4-(4-methoxy-benzyloxy)-1-{(4S,6S)-6-[2-(4-methoxy-benzyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-octan-2-one

Guidance literature:: Multi-step reaction with 8 steps

1.1: 88 percent / Zn / ethanol / 1 h / 70 °C

2.1: 84 percent / DIBALH / toluene / 1.5 h / -78 - 20 °C

3.1: 90 percent / DMAP; Et₃N / CH₂Cl₂ / 72 h / 20 °C

4.1: O₃ / CH₂Cl₂; methanol / -78 °C

4.2: 89 percent / NaBH₄ / CH₂Cl₂; methanol / 1.5 h / 20 °C

5.1: DMAP; Et₃N / CH₂Cl₂ / 1.5 h

6.1: NaI; NaHCO₃ / butan-2-one / 3 h / Heating

7.1: t-BuLi / hexamethylphosphoric acid triamide; tetrahydrofuran / 0.5 h / -78 °C

7.2: 88 percent / hexamethylphosphoric acid triamide; tetrahydrofuran / 0.5 h / -78 °C

8.1: 84 percent / aq. Hg(ClO₄)2 / tetrahydrofuran / 0.17 h

With dmap; mercury(II) perchlorate; tert.-butyl lithium; diisobutylaluminium hydride; sodium hydrogencarbonate; ozone; triethylamine; sodium iodide; zinc; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; ethanol; dichloromethane; toluene; butanone;
DOI:10.1055/s-2004-831334

Reference yield:

: 815588-04-6
[(2R,4S,5S)-5-Iodomethyl-4-(4-methoxy-benzyloxy)-tetrahydro-furan-2-yl]-acetic acid ethyl ester

: 815588-11-5
(4S,6S)-4-{2-[(2S,4S)-4,6-Bis-(tert-butyl-dimethyl-silanyloxy)-2-(4-methoxy-benzyloxy)-hexyl]-[1,3]dithian-2-ylmethyl}-6-[2-(4-methoxy-benzyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxane

Guidance literature:: Multi-step reaction with 7 steps

1.1: 88 percent / Zn / ethanol / 1 h / 70 °C

2.1: 84 percent / DIBALH / toluene / 1.5 h / -78 - 20 °C

3.1: 90 percent / DMAP; Et₃N / CH₂Cl₂ / 72 h / 20 °C

4.1: O₃ / CH₂Cl₂; methanol / -78 °C

4.2: 89 percent / NaBH₄ / CH₂Cl₂; methanol / 1.5 h / 20 °C

5.1: DMAP; Et₃N / CH₂Cl₂ / 1.5 h

6.1: NaI; NaHCO₃ / butan-2-one / 3 h / Heating

7.1: t-BuLi / hexamethylphosphoric acid triamide; tetrahydrofuran / 0.5 h / -78 °C

7.2: 88 percent / hexamethylphosphoric acid triamide; tetrahydrofuran / 0.5 h / -78 °C

With dmap; tert.-butyl lithium; diisobutylaluminium hydride; sodium hydrogencarbonate; ozone; triethylamine; sodium iodide; zinc; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; ethanol; dichloromethane; toluene; butanone;
DOI:10.1055/s-2004-831334