(1S,3S,4R)-4-(tert-butyldimethylsilyloxy)-3-[(tert-butyldimethylsilyloxy)methyl]-1-cyclohexyl-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline

Base Information

Chemical Name:(1S,3S,4R)-4-(tert-butyldimethylsilyloxy)-3-[(tert-butyldimethylsilyloxy)methyl]-1-cyclohexyl-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline
CAS No.:1354006-34-0
Molecular Formula:C₃₁H₅₇NO₄Si₂
Molecular Weight:563.969
Hs Code.:

(1S,3S,4R)-4-(tert-butyldimethylsilyloxy)-3-[(tert-butyldimethylsilyloxy)methyl]-1-cyclohexyl-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline

Synonyms:(1S,3S,4R)-4-(tert-butyldimethylsilyloxy)-3-[(tert-butyldimethylsilyloxy)methyl]-1-cyclohexyl-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline

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Chemical Property of (1S,3S,4R)-4-(tert-butyldimethylsilyloxy)-3-[(tert-butyldimethylsilyloxy)methyl]-1-cyclohexyl-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline

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Technology Process of (1S,3S,4R)-4-(tert-butyldimethylsilyloxy)-3-[(tert-butyldimethylsilyloxy)methyl]-1-cyclohexyl-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline

There total 9 articles about (1S,3S,4R)-4-(tert-butyldimethylsilyloxy)-3-[(tert-butyldimethylsilyloxy)methyl]-1-cyclohexyl-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline 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:

: C₃₁H₅₆NO₄Si₂⁽¹⁺⁾*I^(1-)

: 1354006-34-0
(1S,3S,4R)-4-(tert-butyldimethylsilyloxy)-3-[(tert-butyldimethylsilyloxy)methyl]-1-cyclohexyl-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline

Guidance literature:: With sodium tris(acetoxy)borohydride; In methanol; at 0 ℃; for 0.5h; stereoselective reaction; Inert atmosphere;
DOI:10.1016/j.tet.2011.11.031

Reference yield:

: 1354006-04-4
(3S,4R)-4-(tert-butyldimethylsilyloxy)-3-[(tert-butyldimethylsilyloxy)methyl]-1-cyclohexyl-6,7-dimethoxy-3,4-dihydroisoquinoline

: 1354006-34-0
(1S,3S,4R)-4-(tert-butyldimethylsilyloxy)-3-[(tert-butyldimethylsilyloxy)methyl]-1-cyclohexyl-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline

Guidance literature:: Multi-step reaction with 2 steps

1: dichloromethane / 40 h / 35 °C / Inert atmosphere

2: sodium tris(acetoxy)borohydride / methanol / 0.5 h / 0 °C / Inert atmosphere

With sodium tris(acetoxy)borohydride; In methanol; dichloromethane;
DOI:10.1016/j.tet.2011.11.031

Reference yield:

: 1354006-20-4
(S)-(3,4-dimethoxyphenyl)[(R)-1-(1-phenylethyl)aziridin-2-yl]methanone

: 1354006-34-0
(1S,3S,4R)-4-(tert-butyldimethylsilyloxy)-3-[(tert-butyldimethylsilyloxy)methyl]-1-cyclohexyl-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline

Guidance literature:: Multi-step reaction with 8 steps

1.1: zinc(II) chloride / methanol / 0.5 h / -78 °C / Inert atmosphere

1.2: 3 h / -78 °C / Inert atmosphere

2.1: acetic acid / dichloromethane / 8 h / 20 °C / Inert atmosphere

2.2: Inert atmosphere

2.3: 20 °C / Inert atmosphere

3.1: dmap; triethylamine / dichloromethane / 20 h / 0 °C / Reflux; Inert atmosphere

4.1: hydrogen; palladium(II) hydroxide / 3 h / 760.05 Torr

5.1: sodium hydroxide / tetrahydrofuran; water / 0.08 h / 0 °C / Inert atmosphere

6.1: 2-chloropyridine; trifluoromethylsulfonic anhydride / dichloromethane / -78 - 0 °C / Inert atmosphere

7.1: dichloromethane / 40 h / 35 °C / Inert atmosphere

8.1: sodium tris(acetoxy)borohydride / methanol / 0.5 h / 0 °C / Inert atmosphere

With 2-chloropyridine; dmap; trifluoromethylsulfonic anhydride; hydrogen; palladium(II) hydroxide; sodium tris(acetoxy)borohydride; acetic acid; triethylamine; sodium hydroxide; zinc(II) chloride; In tetrahydrofuran; methanol; dichloromethane; water; 6.1: Bischler-Napieralski reaction;
DOI:10.1016/j.tet.2011.11.031