(2S,4S,5S)-4-[(Z)-(1R,2R,3S,7S,8R,9S)-2,8-Bis-(tert-butyl-dimethyl-silanyloxy)-1,3,7,9-tetramethyl-10-trityloxy-dec-5-enyl]-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxane

Base Information

Chemical Name:(2S,4S,5S)-4-[(Z)-(1R,2R,3S,7S,8R,9S)-2,8-Bis-(tert-butyl-dimethyl-silanyloxy)-1,3,7,9-tetramethyl-10-trityloxy-dec-5-enyl]-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxane
CAS No.:835929-78-7
Molecular Formula:C₅₇H₈₄O₆Si₂
Molecular Weight:921.461
Hs Code.:

(2S,4S,5S)-4-[(Z)-(1R,2R,3S,7S,8R,9S)-2,8-Bis-(tert-butyl-dimethyl-silanyloxy)-1,3,7,9-tetramethyl-10-trityloxy-dec-5-enyl]-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxane

Synonyms:(2S,4S,5S)-4-[(Z)-(1R,2R,3S,7S,8R,9S)-2,8-Bis-(tert-butyl-dimethyl-silanyloxy)-1,3,7,9-tetramethyl-10-trityloxy-dec-5-enyl]-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxane

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Chemical Property of (2S,4S,5S)-4-[(Z)-(1R,2R,3S,7S,8R,9S)-2,8-Bis-(tert-butyl-dimethyl-silanyloxy)-1,3,7,9-tetramethyl-10-trityloxy-dec-5-enyl]-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxane

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Technology Process of (2S,4S,5S)-4-[(Z)-(1R,2R,3S,7S,8R,9S)-2,8-Bis-(tert-butyl-dimethyl-silanyloxy)-1,3,7,9-tetramethyl-10-trityloxy-dec-5-enyl]-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxane

There total 2 articles about (2S,4S,5S)-4-[(Z)-(1R,2R,3S,7S,8R,9S)-2,8-Bis-(tert-butyl-dimethyl-silanyloxy)-1,3,7,9-tetramethyl-10-trityloxy-dec-5-enyl]-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxane 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: 87.0%

: 835929-77-6
(Z)-(2S,3R,4S,8S,9R,10R)-3,9-Bis-(tert-butyl-dimethyl-silanyloxy)-10-[(2S,4S,5S)-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-2,4,8-trimethyl-undec-5-en-1-ol

: 76-83-5
trityl chloride

: 835929-78-7
(2S,4S,5S)-4-[(Z)-(1R,2R,3S,7S,8R,9S)-2,8-Bis-(tert-butyl-dimethyl-silanyloxy)-1,3,7,9-tetramethyl-10-trityloxy-dec-5-enyl]-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxane

Guidance literature:: With pyridine; dmap; for 18h; Heating;
DOI:10.1021/ol047686a

Reference yield:

: 212703-47-4
2,4-dideoxy-3-O-[(1,1-dimethylethyl)dimethylsilyl]-5-O-[(4-methoxyphenyl)-methyl]-2,4-dimethyl-L-arabinose

: 835929-78-7
(2S,4S,5S)-4-[(Z)-(1R,2R,3S,7S,8R,9S)-2,8-Bis-(tert-butyl-dimethyl-silanyloxy)-1,3,7,9-tetramethyl-10-trityloxy-dec-5-enyl]-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxane

Guidance literature:: Multi-step reaction with 4 steps

1.1: NaHMDS / tetrahydrofuran / 0.17 h / 20 °C

1.2: 77 percent / tetrahydrofuran / 0.5 h / -78 °C

2.1: ZnCl₂; t-BuLi / diethyl ether / -78 - 20 °C

2.2: 60 percent / Pd(PPh₃)4 / diethyl ether

3.1: 80 percent / H₂O; DDQ / CH₂Cl₂ / 1 h / 0 °C

4.1: 87 percent / DMAP; pyridine / 18 h / Heating

With pyridine; dmap; water; tert.-butyl lithium; sodium hexamethyldisilazane; 2,3-dicyano-5,6-dichloro-p-benzoquinone; zinc(II) chloride; In tetrahydrofuran; diethyl ether; dichloromethane;
DOI:10.1021/ol047686a