(2R,3S)-3-(benzyloxy)-8-iodo-5-methoxy-7-(methoxymethoxy)-2-(4-methoxyphenyl)chroman

Base Information

Chemical Name:(2R,3S)-3-(benzyloxy)-8-iodo-5-methoxy-7-(methoxymethoxy)-2-(4-methoxyphenyl)chroman
CAS No.:1453207-45-8
Molecular Formula:C₂₆H₂₇IO₆
Molecular Weight:562.401
Hs Code.:

Synonyms:(2R,3S)-3-(benzyloxy)-8-iodo-5-methoxy-7-(methoxymethoxy)-2-(4-methoxyphenyl)chroman

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Chemical Property of (2R,3S)-3-(benzyloxy)-8-iodo-5-methoxy-7-(methoxymethoxy)-2-(4-methoxyphenyl)chroman

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Technology Process of (2R,3S)-3-(benzyloxy)-8-iodo-5-methoxy-7-(methoxymethoxy)-2-(4-methoxyphenyl)chroman

There total 9 articles about (2R,3S)-3-(benzyloxy)-8-iodo-5-methoxy-7-(methoxymethoxy)-2-(4-methoxyphenyl)chroman 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: 99.0%

: 1453207-44-7
(2R,3S)-5-methoxy-7-(methoxymethoxy)-2-(4-methoxyphenyl)chroman-3-ol

: 100-39-0
benzyl bromide

: 1453207-45-8
(2R,3S)-3-(benzyloxy)-8-iodo-5-methoxy-7-(methoxymethoxy)-2-(4-methoxyphenyl)chroman

Guidance literature:: With sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 0 - 20 ℃; for 2h;
DOI:10.1021/ol4021095

Reference yield:

: 480-66-0,67471-34-5
2,4,6-trihydroxyacetophenone

: 1453207-45-8
(2R,3S)-3-(benzyloxy)-8-iodo-5-methoxy-7-(methoxymethoxy)-2-(4-methoxyphenyl)chroman

Guidance literature:: Multi-step reaction with 11 steps

1.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / 0 °C / Inert atmosphere

2.1: potassium carbonate / acetone / 10 h / 80 °C

3.1: hydrogenchloride; water / methanol / 12 h / 30 °C

4.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.17 h / 0 °C

4.2: Claisen-Schmidt Condensation / 12.67 h / 2 - 20 °C

5.1: triethylamine; chloroformic acid ethyl ester / tetrahydrofuran / 0.55 h / 0 °C

5.2: 0.33 h / 20 °C

5.3: 0.75 h / -10 °C

6.1: 1H-imidazole / N,N-dimethyl-formamide / 0 - 20 °C

7.1: hydroquinidein 1,4-phthalazinediyl diether; methanesulfonamide / tert-butyl alcohol; water / 0 °C

8.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1.5 h / 20 °C

9.1: pyridinium p-toluenesulfonate; orthoformic acid triethyl ester / 1,2-dichloro-ethane / 5.33 h / 20 - 50 °C

9.2: 20 °C

10.1: N-iodo-succinimide / N,N-dimethyl-formamide / 0 °C

11.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 2 h / 0 - 20 °C

With 1H-imidazole; hydrogenchloride; N-iodo-succinimide; methanesulfonamide; tetrabutyl ammonium fluoride; water; pyridinium p-toluenesulfonate; chloroformic acid ethyl ester; sodium hydride; potassium carbonate; hydroquinidein 1,4-phthalazinediyl diether; triethylamine; N-ethyl-N,N-diisopropylamine; orthoformic acid triethyl ester; In tetrahydrofuran; methanol; dichloromethane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetone; mineral oil; tert-butyl alcohol; 4.1: |Claisen-Schmidt Condensation / 7.1: |Sharpless Dihydroxylation;
DOI:10.1021/ol4021095

Reference yield:

: 65490-09-7
2'-hydroxy-4',6'-bis(methoxymethoxy)acetophenone

: 1453207-45-8
(2R,3S)-3-(benzyloxy)-8-iodo-5-methoxy-7-(methoxymethoxy)-2-(4-methoxyphenyl)chroman

Guidance literature:: Multi-step reaction with 10 steps

1.1: potassium carbonate / acetone / 10 h / 80 °C

2.1: hydrogenchloride; water / methanol / 12 h / 30 °C

3.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.17 h / 0 °C

3.2: Claisen-Schmidt Condensation / 12.67 h / 2 - 20 °C

4.1: triethylamine; chloroformic acid ethyl ester / tetrahydrofuran / 0.55 h / 0 °C

4.2: 0.33 h / 20 °C

4.3: 0.75 h / -10 °C

5.1: 1H-imidazole / N,N-dimethyl-formamide / 0 - 20 °C

6.1: hydroquinidein 1,4-phthalazinediyl diether; methanesulfonamide / tert-butyl alcohol; water / 0 °C

7.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1.5 h / 20 °C

8.1: pyridinium p-toluenesulfonate; orthoformic acid triethyl ester / 1,2-dichloro-ethane / 5.33 h / 20 - 50 °C

8.2: 20 °C

9.1: N-iodo-succinimide / N,N-dimethyl-formamide / 0 °C

10.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 2 h / 0 - 20 °C

With 1H-imidazole; hydrogenchloride; N-iodo-succinimide; methanesulfonamide; tetrabutyl ammonium fluoride; water; pyridinium p-toluenesulfonate; chloroformic acid ethyl ester; sodium hydride; potassium carbonate; hydroquinidein 1,4-phthalazinediyl diether; triethylamine; orthoformic acid triethyl ester; In tetrahydrofuran; methanol; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetone; mineral oil; tert-butyl alcohol; 3.1: |Claisen-Schmidt Condensation / 6.1: |Sharpless Dihydroxylation;
DOI:10.1021/ol4021095