(1S,2R,4R,5S,7E)-5-<(1S,2R)-2-(benzyloxy)-2-<(p-methoxybenzyl)oxy>-1-<<(p-methoxybenzyl)oxy>methyl>-3-butenyl>-2-(methoxymethoxy)-4,11,11-trimethylbicyclo<6.2.1>undec-7-en-3-one

Base Information

Chemical Name:(1S,2R,4R,5S,7E)-5-<(1S,2R)-2-(benzyloxy)-2-<(p-methoxybenzyl)oxy>-1-<<(p-methoxybenzyl)oxy>methyl>-3-butenyl>-2-(methoxymethoxy)-4,11,11-trimethylbicyclo<6.2.1>undec-7-en-3-one
CAS No.:217819-79-9
Molecular Formula:C₄₄H₅₆O₈
Molecular Weight:712.924
Hs Code.:

(1S,2R,4R,5S,7E)-5-<(1S,2R)-2-(benzyloxy)-2-<(p-methoxybenzyl)oxy>-1-<<(p-methoxybenzyl)oxy>methyl>-3-butenyl>-2-(methoxymethoxy)-4,11,11-trimethylbicyclo<6.2.1>undec-7-en-3-one

Synonyms:(1S,2R,4R,5S,7E)-5-<(1S,2R)-2-(benzyloxy)-2-<(p-methoxybenzyl)oxy>-1-<<(p-methoxybenzyl)oxy>methyl>-3-butenyl>-2-(methoxymethoxy)-4,11,11-trimethylbicyclo<6.2.1>undec-7-en-3-one

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Chemical Property of (1S,2R,4R,5S,7E)-5-<(1S,2R)-2-(benzyloxy)-2-<(p-methoxybenzyl)oxy>-1-<<(p-methoxybenzyl)oxy>methyl>-3-butenyl>-2-(methoxymethoxy)-4,11,11-trimethylbicyclo<6.2.1>undec-7-en-3-one

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Technology Process of (1S,2R,4R,5S,7E)-5-<(1S,2R)-2-(benzyloxy)-2-<(p-methoxybenzyl)oxy>-1-<<(p-methoxybenzyl)oxy>methyl>-3-butenyl>-2-(methoxymethoxy)-4,11,11-trimethylbicyclo<6.2.1>undec-7-en-3-one

There total 1 articles about (1S,2R,4R,5S,7E)-5-<(1S,2R)-2-(benzyloxy)-2-<(p-methoxybenzyl)oxy>-1-<<(p-methoxybenzyl)oxy>methyl>-3-butenyl>-2-(methoxymethoxy)-4,11,11-trimethylbicyclo<6.2.1>undec-7-en-3-one 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:

: 217819-78-8
(1S,2S,3R,4S)-2-<(1Z,3S,4R)-2-(benzyloxy)-4-<(p-methoxybenzyl)oxy>-3-<<(p-methoxybenzyl)oxy>methyl>-1,5-hexadienyl>-3-(methoxymethoxy)-7,7-dimethyl-1-vinylbicyclo<2.2.1>heptan-2-ol

: 74-88-4
methyl iodide

: 217819-79-9
(1S,2R,4R,5S,7E)-5-<(1S,2R)-2-(benzyloxy)-2-<(p-methoxybenzyl)oxy>-1-<<(p-methoxybenzyl)oxy>methyl>-3-butenyl>-2-(methoxymethoxy)-4,11,11-trimethylbicyclo<6.2.1>undec-7-en-3-one

Guidance literature:: With 18-crown-6 ether; potassium hexamethylsilazane; Mechanism; product conformation dependence from reaction temperature, multistep reaction, 1.) toluene, THF, 0 deg C, 5 min; other temperature and time, 2.) toluene, THF, -78 deg C, 2 h;
DOI:10.1021/jo981749j

Reference yield: 30.0%

: 217819-79-9
(1S,2R,4R,5S,7E)-5-<(1S,2R)-2-(benzyloxy)-2-<(p-methoxybenzyl)oxy>-1-<<(p-methoxybenzyl)oxy>methyl>-3-butenyl>-2-(methoxymethoxy)-4,11,11-trimethylbicyclo<6.2.1>undec-7-en-3-one

: (E)-(1S,2R,3S,4R,5S)-5-[(1S,2R)-1-Benzyloxy-2-(4-methoxy-benzyloxy)-1-(4-methoxy-benzyloxymethyl)-but-3-enyl]-2-methoxymethoxy-4,11,11-trimethyl-bicyclo[6.2.1]undec-7-en-3-ol

: (E)-(1S,2R,3R,4R,5S)-5-[(1S,2R)-1-Benzyloxy-2-(4-methoxy-benzyloxy)-1-(4-methoxy-benzyloxymethyl)-but-3-enyl]-2-methoxymethoxy-4,11,11-trimethyl-bicyclo[6.2.1]undec-7-en-3-ol

Guidance literature:: With lithium aluminium tetrahydride; In diethyl ether; at 20 ℃; for 3h;
DOI:10.1021/jo981749j

Reference yield:

: 217819-79-9
(1S,2R,4R,5S,7E)-5-<(1S,2R)-2-(benzyloxy)-2-<(p-methoxybenzyl)oxy>-1-<<(p-methoxybenzyl)oxy>methyl>-3-butenyl>-2-(methoxymethoxy)-4,11,11-trimethylbicyclo<6.2.1>undec-7-en-3-one

: 217819-81-3
(1S,2R,4R,5S,7S,8S)-5-<(1S,2R)-1-(benzyloxy)-4-hydroxy-2-<(p-methoxybenzyl)oxy>-1-<<(p-methoxybenzyl)oxy>methyl>butyl>-7-(tert-butyldimethylsiloxy)-8-hydroxy-2-(methoxymethoxy)-4,11,11-trimethylbicyclo<6.2.1>undecan-3-one

Guidance literature:: Multi-step reaction with 3 steps

1: 1.) pyridine, osmium tetraoxide, 2.) sodium dithionite / 1.) 0 deg C, 1.5 h, 2.) water, 20 deg C, 12 h

2: 208 mg / imidazole / dimethylformamide / 2 h

3: 1.) thexylborane, 2.) NaOH, hydrogen peroxide / 1.) THF, 0 deg C, 100 min, 2.) THF, water, room temperature, 30 min

With pyridine; 1H-imidazole; sodium hydroxide; osmium(VIII) oxide; sodium dithionite; thexylborane; dihydrogen peroxide; In N,N-dimethyl-formamide;
DOI:10.1021/jo981749j