(4R,5R)-(3S,4S,7R,8S,9R,10R,E)-8-((tert-butyldimethylsilyl)oxy)-10-methoxy-12-((4-methoxybenzyl)oxy)-3,5,7,9-tetramethyldodeca-1,5-dien-4-yl 2,2-dimethyl-5-((R,E)-3-methylhexa-1,5-dien-1-yl)-1,3-dioxolane-4-carboxylate

Base Information

Chemical Name:(4R,5R)-(3S,4S,7R,8S,9R,10R,E)-8-((tert-butyldimethylsilyl)oxy)-10-methoxy-12-((4-methoxybenzyl)oxy)-3,5,7,9-tetramethyldodeca-1,5-dien-4-yl 2,2-dimethyl-5-((R,E)-3-methylhexa-1,5-dien-1-yl)-1,3-dioxolane-4-carboxylate
CAS No.:1551543-73-7
Molecular Formula:C₄₄H₇₂O₈Si
Molecular Weight:757.136
Hs Code.:

(4R,5R)-(3S,4S,7R,8S,9R,10R,E)-8-((tert-butyldimethylsilyl)oxy)-10-methoxy-12-((4-methoxybenzyl)oxy)-3,5,7,9-tetramethyldodeca-1,5-dien-4-yl 2,2-dimethyl-5-((R,E)-3-methylhexa-1,5-dien-1-yl)-1,3-dioxolane-4-carboxylate

Synonyms:(4R,5R)-(3S,4S,7R,8S,9R,10R,E)-8-((tert-butyldimethylsilyl)oxy)-10-methoxy-12-((4-methoxybenzyl)oxy)-3,5,7,9-tetramethyldodeca-1,5-dien-4-yl 2,2-dimethyl-5-((R,E)-3-methylhexa-1,5-dien-1-yl)-1,3-dioxolane-4-carboxylate

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Chemical Property of (4R,5R)-(3S,4S,7R,8S,9R,10R,E)-8-((tert-butyldimethylsilyl)oxy)-10-methoxy-12-((4-methoxybenzyl)oxy)-3,5,7,9-tetramethyldodeca-1,5-dien-4-yl 2,2-dimethyl-5-((R,E)-3-methylhexa-1,5-dien-1-yl)-1,3-dioxolane-4-carboxylate

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Technology Process of (4R,5R)-(3S,4S,7R,8S,9R,10R,E)-8-((tert-butyldimethylsilyl)oxy)-10-methoxy-12-((4-methoxybenzyl)oxy)-3,5,7,9-tetramethyldodeca-1,5-dien-4-yl 2,2-dimethyl-5-((R,E)-3-methylhexa-1,5-dien-1-yl)-1,3-dioxolane-4-carboxylate

There total 12 articles about (4R,5R)-(3S,4S,7R,8S,9R,10R,E)-8-((tert-butyldimethylsilyl)oxy)-10-methoxy-12-((4-methoxybenzyl)oxy)-3,5,7,9-tetramethyldodeca-1,5-dien-4-yl 2,2-dimethyl-5-((R,E)-3-methylhexa-1,5-dien-1-yl)-1,3-dioxolane-4-carboxylate 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%

: 1551543-35-1
(4R,5R)-2,2-dimethyl-5-((R,E)-3-methylhexa-1,5-dien-1-yl)-1,3-dioxolane-4-carboxylic acid

: 1551543-36-2
(3S,4S,7R,8S,9R,10R,E)-8-((tert-butyldimethylsilyl)oxy)-10-methoxy-12-((4-methoxybenzyl)oxy)-3,5,7,9-tetramethyldodeca-1,5-dien-4-ol

: 1551543-73-7
(4R,5R)-(3S,4S,7R,8S,9R,10R,E)-8-((tert-butyldimethylsilyl)oxy)-10-methoxy-12-((4-methoxybenzyl)oxy)-3,5,7,9-tetramethyldodeca-1,5-dien-4-yl 2,2-dimethyl-5-((R,E)-3-methylhexa-1,5-dien-1-yl)-1,3-dioxolane-4-carboxylate

Guidance literature:: With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20 ℃; for 14h; Inert atmosphere;
DOI:10.1021/ol500004k

Reference yield:

: 1551543-71-5
(4R,5S,6S,7R,E)-methyl 5-((tert-butyldimethylsilyl)oxy)-7-methoxy-9-((4-methoxybenzyl)oxy)-2,4,6-trimethylnon-2-enoate

: 1551543-73-7
(4R,5R)-(3S,4S,7R,8S,9R,10R,E)-8-((tert-butyldimethylsilyl)oxy)-10-methoxy-12-((4-methoxybenzyl)oxy)-3,5,7,9-tetramethyldodeca-1,5-dien-4-yl 2,2-dimethyl-5-((R,E)-3-methylhexa-1,5-dien-1-yl)-1,3-dioxolane-4-carboxylate

Guidance literature:: Multi-step reaction with 4 steps

1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 0 °C

2: Dess-Martin periodane / dichloromethane / 0 °C

3: (R,R)-trans-EZ-crotyl mix / dichloromethane / 40 h / 20 °C

4: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / 14 h / 20 °C / Inert atmosphere

With dmap; lithium aluminium tetrahydride; (R,R)-trans-EZ-crotyl mix; Dess-Martin periodane; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; dichloromethane;
DOI:10.1021/ol500004k

Reference yield:

: (3aR,4S,6S,6aR)-2,2-dimethyl-6-((Z)-prop-1-en-1-yl)tetrahydrofuro[3,4-d][1,3]dioxol-4-ol

: 1551543-73-7
(4R,5R)-(3S,4S,7R,8S,9R,10R,E)-8-((tert-butyldimethylsilyl)oxy)-10-methoxy-12-((4-methoxybenzyl)oxy)-3,5,7,9-tetramethyldodeca-1,5-dien-4-yl 2,2-dimethyl-5-((R,E)-3-methylhexa-1,5-dien-1-yl)-1,3-dioxolane-4-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

1.1: chlorodimethylsulfonium chloride / dichloromethane / 2.5 h / -78 °C

1.2: 4 h / -78 - 20 °C

2.1: copper(I) bromide dimethylsulfide complex; dimethylsulfide / tetrahydrofuran; diethyl ether / 0.25 h / -50 °C

2.2: 2 h / -50 - -15 °C

3.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / 14 h / 20 °C / Inert atmosphere

With dmap; copper(I) bromide dimethylsulfide complex; dimethylsulfide; chlorodimethylsulfonium chloride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; diethyl ether; dichloromethane; 1.1: |Swern Oxidation / 1.2: |Swern Oxidation;
DOI:10.1021/ol500004k