(3R,4R,5R,6R,E)-tert-butyl 8-iodo-3-methoxy-5-[(4-methoxybenzyl)oxy]-4,6-dimethylnon-7-enoate

Base Information

Chemical Name:(3R,4R,5R,6R,E)-tert-butyl 8-iodo-3-methoxy-5-[(4-methoxybenzyl)oxy]-4,6-dimethylnon-7-enoate
CAS No.:1360572-07-1
Molecular Formula:C₂₄H₃₇IO₅
Molecular Weight:532.459
Hs Code.:

Synonyms:(3R,4R,5R,6R,E)-tert-butyl 8-iodo-3-methoxy-5-[(4-methoxybenzyl)oxy]-4,6-dimethylnon-7-enoate

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Chemical Property of (3R,4R,5R,6R,E)-tert-butyl 8-iodo-3-methoxy-5-[(4-methoxybenzyl)oxy]-4,6-dimethylnon-7-enoate

Chemical Property:

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Technology Process of (3R,4R,5R,6R,E)-tert-butyl 8-iodo-3-methoxy-5-[(4-methoxybenzyl)oxy]-4,6-dimethylnon-7-enoate

There total 11 articles about (3R,4R,5R,6R,E)-tert-butyl 8-iodo-3-methoxy-5-[(4-methoxybenzyl)oxy]-4,6-dimethylnon-7-enoate 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: 73.0%

: 1360572-01-5
(3R,4R,5R,6R)-tert-butyl 3-methoxy-5-[(4-methoxybenzyl)oxy]-4,6-dimethylnon-7-ynoate

: 1360572-07-1
(3R,4R,5R,6R,E)-tert-butyl 8-iodo-3-methoxy-5-[(4-methoxybenzyl)oxy]-4,6-dimethylnon-7-enoate

Guidance literature:: (3R,4R,5R,6R)-tert-butyl 3-methoxy-5-[(4-methoxybenzyl)oxy]-4,6-dimethylnon-7-ynoate; With Schwartz's reagent; In benzene; Inert atmosphere; Heating;

With iodine; In dichloromethane; benzene; at -25 ℃; Inert atmosphere;
DOI:10.1002/anie.201106762

Reference yield:

: 1360572-18-4
(2R,3R,4R)-2,4-dimethylhept-5-yn-1,3-diol

: 1360572-07-1
(3R,4R,5R,6R,E)-tert-butyl 8-iodo-3-methoxy-5-[(4-methoxybenzyl)oxy]-4,6-dimethylnon-7-enoate

Guidance literature:: Multi-step reaction with 6 steps

1.1: pyridinium p-toluenesulfonate / dichloromethane / 1 h / Molecular sieve; Inert atmosphere

2.1: diisobutylaluminium hydride / hexane; dichloromethane / 3.83 h / -78 - 20 °C / Inert atmosphere

3.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1.58 h / -78 - -40 °C / Inert atmosphere

3.2: -40 - 20 °C / Inert atmosphere

4.1: boron trifluoride diethyl etherate / toluene / 0.5 h / -78 °C / Inert atmosphere

5.1: N,N,N',N'-tetramethyl-1,8-diaminonaphthalene / dichloromethane / 20 °C / Inert atmosphere

6.1: Schwartz's reagent / benzene / Inert atmosphere; Heating

6.2: -25 °C / Inert atmosphere

With Schwartz's reagent; oxalyl dichloride; boron trifluoride diethyl etherate; pyridinium p-toluenesulfonate; N,N,N',N'-tetramethyl-1,8-diaminonaphthalene; diisobutylaluminium hydride; dimethyl sulfoxide; In hexane; dichloromethane; toluene; benzene; 3.1: Swarts reaction;
DOI:10.1002/anie.201106762

Reference yield:

: 27301-54-8,57984-70-0,58072-60-9,90242-65-2
(S)-(+)-pent-3-yn-2-ol

: 1360572-07-1
(3R,4R,5R,6R,E)-tert-butyl 8-iodo-3-methoxy-5-[(4-methoxybenzyl)oxy]-4,6-dimethylnon-7-enoate

Guidance literature:: Multi-step reaction with 9 steps

1.1: triethylamine / dichloromethane / 2 h / -78 °C / Inert atmosphere

2.1: indium iodide; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide / 17 h / 20 °C / Inert atmosphere

3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 13.58 h / 0 - 20 °C / Inert atmosphere

4.1: pyridinium p-toluenesulfonate / dichloromethane / 1 h / Molecular sieve; Inert atmosphere

5.1: diisobutylaluminium hydride / hexane; dichloromethane / 3.83 h / -78 - 20 °C / Inert atmosphere

6.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1.58 h / -78 - -40 °C / Inert atmosphere

6.2: -40 - 20 °C / Inert atmosphere

7.1: boron trifluoride diethyl etherate / toluene / 0.5 h / -78 °C / Inert atmosphere

8.1: N,N,N',N'-tetramethyl-1,8-diaminonaphthalene / dichloromethane / 20 °C / Inert atmosphere

9.1: Schwartz's reagent / benzene / Inert atmosphere; Heating

9.2: -25 °C / Inert atmosphere

With Schwartz's reagent; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; oxalyl dichloride; indium iodide; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; N,N,N',N'-tetramethyl-1,8-diaminonaphthalene; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; dichloromethane; toluene; benzene; 2.1: Marshall reaction / 6.1: Swarts reaction;
DOI:10.1002/anie.201106762