(2S,3R,4R,6R)-1,4-bis[(tert-butyldimethylsilyl)oxy]-7,7-(ethylenedithio)-3-[(4-methoxybenzyl)oxy]-2,4,6-trimethylnonane

Base Information

• Chemical Name: (2S,3R,4R,6R)-1,4-bis[(tert-butyldimethylsilyl)oxy]-7,7-(ethylenedithio)-3-[(4-methoxybenzyl)oxy]-2,4,6-trimethylnonane
• CAS No.: 188785-95-7
• Molecular Formula: C₃₄H₆₄O₄S₂Si₂
• Molecular Weight: 657.183
• Mol file: 188785-95-7.mol

Synonyms:(2S,3R,4R,6R)-1,4-bis[(tert-butyldimethylsilyl)oxy]-7,7-(ethylenedithio)-3-[(4-methoxybenzyl)oxy]-2,4,6-trimethylnonane

Chemical Property of (2S,3R,4R,6R)-1,4-bis[(tert-butyldimethylsilyl)oxy]-7,7-(ethylenedithio)-3-[(4-methoxybenzyl)oxy]-2,4,6-trimethylnonane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R,4R,6R)-1,4-bis[(tert-butyldimethylsilyl)oxy]-7,7-(ethylenedithio)-3-[(4-methoxybenzyl)oxy]-2,4,6-trimethylnonane

There total 6 articles about (2S,3R,4R,6R)-1,4-bis[(tert-butyldimethylsilyl)oxy]-7,7-(ethylenedithio)-3-[(4-methoxybenzyl)oxy]-2,4,6-trimethylnonane 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%

(2S,3R,4R,6R)-4-[(tert-butyldimethylsilyl)oxy]-7,7-(ethylenedithio)-3-[(4-methoxybenzyl)oxy]-2,4,6-trimethylnonane (944740-60-7) + t-butyldimethylsiyl triflate (69739-34-0) → (2S,3R,4R,6R)-1,4-bis[(tert-butyldimethylsilyl)oxy]-7,7-(ethylenedithio)-3-[(4-methoxybenzyl)oxy]-2,4,6-trimethylnonane (188785-95-7)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 ℃; for 1h;

DOI:10.1016/j.tet.2007.02.044

Reference yield:

t-butyldimethylsiyl triflate (69739-34-0) + tert-Butyl-{(1R,3R)-3-(2-ethyl-[1,3]dithiolan-2-yl)-1-[(4R,5S)-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-1-methyl-butoxy}-dimethyl-silane (188785-91-3) → (2S,3R,4R,6R)-1,4-bis[(tert-butyldimethylsilyl)oxy]-7,7-(ethylenedithio)-3-[(4-methoxybenzyl)oxy]-2,4,6-trimethylnonane (188785-95-7)

Guidance literature:

With aluminium trichloride; borane-THF; N-ethyl-N,N-diisopropylamine; Yield given. Multistep reaction;

DOI:10.1021/ja963575y

Reference yield:

(2S,3R,4R,6R)-4-[(tert-butyldimethylsilyl)oxy]-7,7-(ethylenedithio)-1,3-{[(R)-4-methoxybenzylidene]dioxy}-2,4,6-trimethylnonane (944740-59-4) → (2S,3R,4R,6R)-1,4-bis[(tert-butyldimethylsilyl)oxy]-7,7-(ethylenedithio)-3-[(4-methoxybenzyl)oxy]-2,4,6-trimethylnonane (188785-95-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 96 percent / BH₃*THF; AlCl₃ / diethyl ether; tetrahydrofuran / 3 h / 20 °C

2: 99 percent / ethyldiisopropylamine / CH₂Cl₂ / 1 h / 0 °C

With aluminium trichloride; borane-THF; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; diethyl ether; dichloromethane;

DOI:10.1016/j.tet.2007.02.044

upstream raw materials:

t-butyldimethylsiyl triflate

tert-Butyl-{(1R,3R)-3-(2-ethyl-[1,3]dithiolan-2-yl)-1-[(4R,5S)-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-1-methyl-butoxy}-dimethyl-silane

(2S,3R,4R,6R)-4-[(tert-butyldimethylsilyl)oxy]-7,7-(ethylenedithio)-3-[(4-methoxybenzyl)oxy]-2,4,6-trimethylnonane

(2S,3R,4R,6R)-7,7-(ethylenedithio)-1,3-{[(R)-4-methoxybenzylidene]dioxy}-2,4,6-trimethylnonan-4-ol

Downstream raw materials:

(2S,3R,4R,6R,8R,9S,10R,11R)-11-[(benzyloxy)methoxy]-1,4-bis[(tert-butyldimethylsilyl)oxy]-9-hydroxy-3-[(4-methoxybenzyl)oxy]-2,4,6,8,10-pentamethyltridecan-7-one

(2S,3R,4R,6R,7S,8S,9R,10R,11R)-11-[(benzyloxy)methoxy]-1,4-bis[(tert-butyldimethylsilyl)oxy]-3-[(4-methoxybenzyl)oxy]-2,4,6,8,10-pentamethyltridecane-7,9-diol

(2S,3R,4R,6R,7S,8S,9S,10S,11R)-11-[(benzyloxy)methoxy]-4-[(tert-butyldimethylsilyl)oxy]-3-[(4-methoxybenzyl)oxy]-2,4,6,8,10-pentamethyl-7,9-{[(R)-2,4,6-trimethylbenzylidene]dioxy}tridecanol

(2R,3S,4S,5R,6R,7R,9S,10S,11S,12S,13R)-13-[(benzyloxy)methoxy]-6-[(tert-butyldimethylsilyl)oxy]-3,5-{[(R)-4-methoxybenzylidene]dioxy}-2,4,6,8,10,12-hexamethyl-9,11-{[(R)-2,4,6-trimethylbenzylidene]dioxy}pentadecanal