(E)-1'-(5-((2R,4R,5S,6R)-5-benzyloxy-4-dimethylamino-6-methyltetrahydro-2H-pyran-2-yl)-9,10-dimethoxy-1-(methoxymethoxy)-3-methyl-8-(triisopropylsilyloxy)anthracen-2-yl)-4'-methylhex-4'-en-2'-yn-1'-ol

Base Information

Chemical Name:(E)-1'-(5-((2R,4R,5S,6R)-5-benzyloxy-4-dimethylamino-6-methyltetrahydro-2H-pyran-2-yl)-9,10-dimethoxy-1-(methoxymethoxy)-3-methyl-8-(triisopropylsilyloxy)anthracen-2-yl)-4'-methylhex-4'-en-2'-yn-1'-ol
CAS No.:1255790-50-1
Molecular Formula:C₅₀H₆₉NO₈Si
Molecular Weight:840.185
Hs Code.:

(E)-1'-(5-((2R,4R,5S,6R)-5-benzyloxy-4-dimethylamino-6-methyltetrahydro-2H-pyran-2-yl)-9,10-dimethoxy-1-(methoxymethoxy)-3-methyl-8-(triisopropylsilyloxy)anthracen-2-yl)-4'-methylhex-4'-en-2'-yn-1'-ol

Synonyms:(E)-1'-(5-((2R,4R,5S,6R)-5-benzyloxy-4-dimethylamino-6-methyltetrahydro-2H-pyran-2-yl)-9,10-dimethoxy-1-(methoxymethoxy)-3-methyl-8-(triisopropylsilyloxy)anthracen-2-yl)-4'-methylhex-4'-en-2'-yn-1'-ol

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Chemical Property of (E)-1'-(5-((2R,4R,5S,6R)-5-benzyloxy-4-dimethylamino-6-methyltetrahydro-2H-pyran-2-yl)-9,10-dimethoxy-1-(methoxymethoxy)-3-methyl-8-(triisopropylsilyloxy)anthracen-2-yl)-4'-methylhex-4'-en-2'-yn-1'-ol

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Technology Process of (E)-1'-(5-((2R,4R,5S,6R)-5-benzyloxy-4-dimethylamino-6-methyltetrahydro-2H-pyran-2-yl)-9,10-dimethoxy-1-(methoxymethoxy)-3-methyl-8-(triisopropylsilyloxy)anthracen-2-yl)-4'-methylhex-4'-en-2'-yn-1'-ol

There total 8 articles about (E)-1'-(5-((2R,4R,5S,6R)-5-benzyloxy-4-dimethylamino-6-methyltetrahydro-2H-pyran-2-yl)-9,10-dimethoxy-1-(methoxymethoxy)-3-methyl-8-(triisopropylsilyloxy)anthracen-2-yl)-4'-methylhex-4'-en-2'-yn-1'-ol 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: 75.0%

: 1255790-47-6
(E)-4-methylhex-4-en-2-ynal

: 1255790-49-8
(2R,3S,4R,6R)-3-(benzyloxy)-6-(6-bromo-9,10-dimethoxy-5-(methoxymethoxy)-7-methyl-4-((triisopropylsilyl)oxy)anthracen-1-yl)-N,N,2-trimethyltetrahydro-2H-pyran-4-amine

: 1255790-50-1
(E)-1'-(5-((2R,4R,5S,6R)-5-benzyloxy-4-dimethylamino-6-methyltetrahydro-2H-pyran-2-yl)-9,10-dimethoxy-1-(methoxymethoxy)-3-methyl-8-(triisopropylsilyloxy)anthracen-2-yl)-4'-methylhex-4'-en-2'-yn-1'-ol

: (2R,3S,4R,6R)-3-(benzyloxy)-6-(9,10-dimethoxy-5-(methoxymethoxy)-7-methyl-4-((triisopropylsilyl)oxy)anthracen-1-yl)-N,N,2-trimethyltetrahydro-2H-pyran-4-amine

Guidance literature:: (2R,3S,4R,6R)-3-(benzyloxy)-6-(6-bromo-9,10-dimethoxy-5-(methoxymethoxy)-7-methyl-4-((triisopropylsilyl)oxy)anthracen-1-yl)-N,N,2-trimethyltetrahydro-2H-pyran-4-amine; With tert.-butyl lithium; In tetrahydrofuran; pentane; at -78 ℃; for 0.00277778h; Inert atmosphere;

(E)-4-methylhex-4-en-2-ynal; In tetrahydrofuran; pentane; at -78 - 20 ℃; Inert atmosphere;

With water; In tetrahydrofuran; pentane; at 20 ℃; Inert atmosphere;
DOI:10.1016/j.tet.2011.05.117

Reference yield: 75.0%

: 1255790-47-6
(E)-4-methylhex-4-en-2-ynal

: 1255790-49-8
(2R,3S,4R,6R)-3-(benzyloxy)-6-(6-bromo-9,10-dimethoxy-5-(methoxymethoxy)-7-methyl-4-((triisopropylsilyl)oxy)anthracen-1-yl)-N,N,2-trimethyltetrahydro-2H-pyran-4-amine

: 1255790-50-1
(E)-1'-(5-((2R,4R,5S,6R)-5-benzyloxy-4-dimethylamino-6-methyltetrahydro-2H-pyran-2-yl)-9,10-dimethoxy-1-(methoxymethoxy)-3-methyl-8-(triisopropylsilyloxy)anthracen-2-yl)-4'-methylhex-4'-en-2'-yn-1'-ol

Guidance literature:: (2R,3S,4R,6R)-3-(benzyloxy)-6-(6-bromo-9,10-dimethoxy-5-(methoxymethoxy)-7-methyl-4-((triisopropylsilyl)oxy)anthracen-1-yl)-N,N,2-trimethyltetrahydro-2H-pyran-4-amine; With tert.-butyl lithium; In tetrahydrofuran; pentane; at -78 ℃; for 0.00277778h; Inert atmosphere;

(E)-4-methylhex-4-en-2-ynal; In tetrahydrofuran; pentane; at -78 ℃; for 0.0333333h; Inert atmosphere;
DOI:10.1021/ja107926f

Reference yield:

: 80522-42-5
triisopropylsilyl trifluoromethanesulfonate

: 1255790-50-1
(E)-1'-(5-((2R,4R,5S,6R)-5-benzyloxy-4-dimethylamino-6-methyltetrahydro-2H-pyran-2-yl)-9,10-dimethoxy-1-(methoxymethoxy)-3-methyl-8-(triisopropylsilyloxy)anthracen-2-yl)-4'-methylhex-4'-en-2'-yn-1'-ol

: (2R,3S,4R,6R)-3-(benzyloxy)-6-(9,10-dimethoxy-5-(methoxymethoxy)-7-methyl-4-((triisopropylsilyl)oxy)anthracen-1-yl)-N,N,2-trimethyltetrahydro-2H-pyran-4-amine

Guidance literature:: Multi-step reaction with 5 steps

1.1: 2,6-dimethylpyridine / dichloromethane / 21 h / 0 - 20 °C / Inert atmosphere

2.1: pyridine; 20% palladium hydroxide on carbon; hydrogen / methanol; ethyl acetate / 2 h

3.1: N-Bromosuccinimide / dichloromethane / 4 h / -78 - 20 °C / Inert atmosphere

4.1: sodium hydride / tetrahydrofuran; mineral oil / 0.42 h / 0 - 20 °C / Inert atmosphere

5.1: tert.-butyl lithium / tetrahydrofuran; pentane / 0 h / -78 °C / Inert atmosphere

5.2: -78 - 20 °C / Inert atmosphere

5.3: 20 °C / Inert atmosphere

With pyridine; 2,6-dimethylpyridine; N-Bromosuccinimide; 20% palladium hydroxide on carbon; hydrogen; tert.-butyl lithium; sodium hydride; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; mineral oil; pentane;
DOI:10.1016/j.tet.2011.05.117