tert-butyl {(4R,6E,8S,10E,12S,14S,16S)-4,14,16-tris{[tert-butyl(dimethyl)silyl]oxy}-8,12-dihydroxy-18-[(4-methoxybenzyl)-oxy]octadeca-6,10-dien-1-yl}carbamate

Base Information

• Chemical Name: tert-butyl {(4R,6E,8S,10E,12S,14S,16S)-4,14,16-tris{[tert-butyl(dimethyl)silyl]oxy}-8,12-dihydroxy-18-[(4-methoxybenzyl)-oxy]octadeca-6,10-dien-1-yl}carbamate
• CAS No.: 1274953-68-2
• Molecular Formula: C₄₉H₉₃NO₉Si₃
• Molecular Weight: 924.535

Synonyms:tert-butyl {(4R,6E,8S,10E,12S,14S,16S)-4,14,16-tris{[tert-butyl(dimethyl)silyl]oxy}-8,12-dihydroxy-18-[(4-methoxybenzyl)-oxy]octadeca-6,10-dien-1-yl}carbamate

Chemical Property of tert-butyl {(4R,6E,8S,10E,12S,14S,16S)-4,14,16-tris{[tert-butyl(dimethyl)silyl]oxy}-8,12-dihydroxy-18-[(4-methoxybenzyl)-oxy]octadeca-6,10-dien-1-yl}carbamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of tert-butyl {(4R,6E,8S,10E,12S,14S,16S)-4,14,16-tris{[tert-butyl(dimethyl)silyl]oxy}-8,12-dihydroxy-18-[(4-methoxybenzyl)-oxy]octadeca-6,10-dien-1-yl}carbamate

There total 25 articles about tert-butyl {(4R,6E,8S,10E,12S,14S,16S)-4,14,16-tris{[tert-butyl(dimethyl)silyl]oxy}-8,12-dihydroxy-18-[(4-methoxybenzyl)-oxy]octadeca-6,10-dien-1-yl}carbamate 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: 83.0%

tert-butyl ((4R,6E)-4-{[tert-butyl(dimethyl)silyl]oxy}-8-oxooct-6-en-1-yl)carbamate (1274953-66-0) + (3S,5S)-3,5-bis-(tert-butyldimethylsilanyloxy)-7-(4-methoxy-benzyloxy)-heptane-1-al (1274953-67-1) + N,N,N-tributylbutan-1-aminium trifluoro(propa-1,2-dien-1-yl)borate (1275575-88-6) → tert-butyl {(4R,6E,8S,10E,12S,14S,16S)-4,14,16-tris{[tert-butyl(dimethyl)silyl]oxy}-8,12-dihydroxy-18-[(4-methoxybenzyl)-oxy]octadeca-6,10-dien-1-yl}carbamate (1274953-68-2)

Guidance literature:

N,N,N-tributylbutan-1-aminium trifluoro(propa-1,2-dien-1-yl)borate; With chloro-trimethyl-silane; lithium-B-H₂-(10R)-trimethylsilyl-9-borabicyclo[3.3.2]decane; In dichloromethane; toluene; at -78 - -30 ℃; Inert atmosphere;

(3S,5S)-3,5-bis-(tert-butyldimethylsilanyloxy)-7-(4-methoxy-benzyloxy)-heptane-1-al; In dichloromethane; toluene; at -78 ℃; for 4h; Inert atmosphere;

tert-butyl ((4R,6E)-4-{[tert-butyl(dimethyl)silyl]oxy}-8-oxooct-6-en-1-yl)carbamate; optical yield given as %de; Further stages;

DOI:10.1016/j.tet.2011.06.008

Reference yield:

tert-butyl ((4R,6E)-4-{[tert-butyl(dimethyl)silyl]oxy}-8-oxooct-6-en-1-yl)carbamate (1274953-66-0) + (3S,5S)-3,5-bis-(tert-butyldimethylsilanyloxy)-7-(4-methoxy-benzyloxy)-heptane-1-al (1274953-67-1) + allenyltributylstannane (53915-69-8) → tert-butyl {(4R,6E,8S,10E,12S,14S,16S)-4,14,16-tris{[tert-butyl(dimethyl)silyl]oxy}-8,12-dihydroxy-18-[(4-methoxybenzyl)-oxy]octadeca-6,10-dien-1-yl}carbamate (1274953-68-2) + tert-butyl {(4R,6E,10E,14S,16S)-4,14,16-tris{[tert-butyl(dimethyl)silyl]oxy}-8,12-dihydroxy-18-[(4-methoxybenzyl)-oxy]octadeca-6,10-dien-1-yl}carbamate

Guidance literature:

allenyltributylstannane; With chloro-trimethyl-silane; lithium-B-H₂-(10R)-trimethylsilyl-9-borabicyclo[3.3.2]decane; In dichloromethane; toluene; at -78 - -30 ℃; Inert atmosphere;

(3S,5S)-3,5-bis-(tert-butyldimethylsilanyloxy)-7-(4-methoxy-benzyloxy)-heptane-1-al; In dichloromethane; toluene; at -78 ℃; for 4h; Inert atmosphere;

tert-butyl ((4R,6E)-4-{[tert-butyl(dimethyl)silyl]oxy}-8-oxooct-6-en-1-yl)carbamate; optical yield given as %de; Further stages;

DOI:10.1016/j.tet.2011.06.008

Reference yield:

tert-butyl ((4R,6E)-4-{[tert-butyl(dimethyl)silyl]oxy}-8-oxooct-6-en-1-yl)carbamate (1274953-66-0) + (3S,5S)-3,5-bis-(tert-butyldimethylsilanyloxy)-7-(4-methoxy-benzyloxy)-heptane-1-al (1274953-67-1) + 2-allenyl-[1,3,2]-dioxaborinane (169517-16-2) → tert-butyl {(4R,6E,8S,10E,12S,14S,16S)-4,14,16-tris{[tert-butyl(dimethyl)silyl]oxy}-8,12-dihydroxy-18-[(4-methoxybenzyl)-oxy]octadeca-6,10-dien-1-yl}carbamate (1274953-68-2) + tert-butyl {(4R,6E,10E,14S,16S)-4,14,16-tris{[tert-butyl(dimethyl)silyl]oxy}-8,12-dihydroxy-18-[(4-methoxybenzyl)-oxy]octadeca-6,10-dien-1-yl}carbamate + tert-butyl {(4R,6E,8S,10Z,12S,14S,16S)-4,14,16-tris{[tert-butyl(dimethyl)silyl]oxy}-8,12-dihydroxy-18-[(4-methoxybenzyl)-oxy]octadeca-6,10-dien-1-yl}carbamate

Guidance literature:

2-allenyl-[1,3,2]-dioxaborinane; With chloro-trimethyl-silane; lithium-B-H₂-(10R)-trimethylsilyl-9-borabicyclo[3.3.2]decane; In dichloromethane; toluene; at -78 - -30 ℃; Inert atmosphere;

(3S,5S)-3,5-bis-(tert-butyldimethylsilanyloxy)-7-(4-methoxy-benzyloxy)-heptane-1-al; In dichloromethane; toluene; at -78 ℃; for 4h; Inert atmosphere;

tert-butyl ((4R,6E)-4-{[tert-butyl(dimethyl)silyl]oxy}-8-oxooct-6-en-1-yl)carbamate; Further stages;

DOI:10.1016/j.tet.2011.06.008

upstream raw materials:

tert-butyl ((4R,6E)-4-{[tert-butyl(dimethyl)silyl]oxy}-8-oxooct-6-en-1-yl)carbamate

(S,E)-8-(4-methoxy-benzyloxy)-octa-1,5-dien-4-ol

(S)-1-((2S,3S)-3-(2-(4-methoxy-benzyloxy)-ethyl)oxiran-2-yl)-but-3-en-1-ol

(3S,5S)-1-(4-methoxy-benzyloxy)-oct-7-ene-3,5-diol

Downstream raw materials:

5.10.5. tert-butyl {(4R,6E,8S,10E,12S,14R,16S)-4,8,12,14,16-pentakis{[tert-butyl(dimethyl)silyl]oxy}-18-[(4-methoxybenzyl)oxy]octadeca-6,10-dien-1-yl}carbamate

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