(2S,3R,4S,5R,6R,7S,10S,11R,12R,13R)-1,11-di-O-benzyl-13-O-(tert-butyldimethylsilyl)-2,4,6,8,10,12-hexamethyl-3,5-O-isopropylidene-7-(thiophenoxy)-8(E)-pentadecene-1,3,5,6,11,13-hexol

Base Information

Chemical Name:(2S,3R,4S,5R,6R,7S,10S,11R,12R,13R)-1,11-di-O-benzyl-13-O-(tert-butyldimethylsilyl)-2,4,6,8,10,12-hexamethyl-3,5-O-isopropylidene-7-(thiophenoxy)-8(E)-pentadecene-1,3,5,6,11,13-hexol
CAS No.:131681-73-7
Molecular Formula:C₅₀H₇₆O₆SSi
Molecular Weight:833.301
Hs Code.:

(2S,3R,4S,5R,6R,7S,10S,11R,12R,13R)-1,11-di-O-benzyl-13-O-(tert-butyldimethylsilyl)-2,4,6,8,10,12-hexamethyl-3,5-O-isopropylidene-7-(thiophenoxy)-8(E)-pentadecene-1,3,5,6,11,13-hexol

Synonyms:(2S,3R,4S,5R,6R,7S,10S,11R,12R,13R)-1,11-di-O-benzyl-13-O-(tert-butyldimethylsilyl)-2,4,6,8,10,12-hexamethyl-3,5-O-isopropylidene-7-(thiophenoxy)-8(E)-pentadecene-1,3,5,6,11,13-hexol

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Chemical Property of (2S,3R,4S,5R,6R,7S,10S,11R,12R,13R)-1,11-di-O-benzyl-13-O-(tert-butyldimethylsilyl)-2,4,6,8,10,12-hexamethyl-3,5-O-isopropylidene-7-(thiophenoxy)-8(E)-pentadecene-1,3,5,6,11,13-hexol

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Technology Process of (2S,3R,4S,5R,6R,7S,10S,11R,12R,13R)-1,11-di-O-benzyl-13-O-(tert-butyldimethylsilyl)-2,4,6,8,10,12-hexamethyl-3,5-O-isopropylidene-7-(thiophenoxy)-8(E)-pentadecene-1,3,5,6,11,13-hexol

There total 20 articles about (2S,3R,4S,5R,6R,7S,10S,11R,12R,13R)-1,11-di-O-benzyl-13-O-(tert-butyldimethylsilyl)-2,4,6,8,10,12-hexamethyl-3,5-O-isopropylidene-7-(thiophenoxy)-8(E)-pentadecene-1,3,5,6,11,13-hexol 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:

: 100-39-0
benzyl bromide

: 131681-73-7
(2S,3R,4S,5R,6R,7S,10S,11R,12R,13R)-1,11-di-O-benzyl-13-O-(tert-butyldimethylsilyl)-2,4,6,8,10,12-hexamethyl-3,5-O-isopropylidene-7-(thiophenoxy)-8(E)-pentadecene-1,3,5,6,11,13-hexol

Guidance literature:: Multi-step reaction with 10 steps

1: 1.) NaH / 1.) DMF, 0 deg C, 2.) from -50 deg C to RT, overnight

2: 96 percent / formic acid / diethyl ether / 22 °C

3: oxalyl chloride/DMSO / CH₂Cl₂ / 0.33 h / -78 °C

4: 62 percent / diethyl ether / 2 h / 22 °C

5: 97 percent / imidazole / dimethylformamide / 48 h / 60 °C

6: 1.) ozone, 2.) Ph₃P / 1.) CH₂Cl₂, -78 deg C, 2.) from -78 deg C to RT

7: 95 percent / tetrahydrofuran / 72 h / 22 °C

8: 95 percent / DIBAL / toluene / 0.25 h / -10 °C

9: 98 percent / pyridine, n-Bu₃P / 22 °C

10: 1.) n-BuLi, TMEDA / 1.) hexane, -40 deg C, 30 min, 2.) THF, HMPA, -78 deg C, 2 min

With pyridine; 1H-imidazole; n-butyllithium; formic acid; oxalyl dichloride; N,N,N,N,-tetramethylethylenediamine; tributylphosphine; sodium hydride; diisobutylaluminium hydride; ozone; dimethyl sulfoxide; triphenylphosphine; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1021/ja00003a026

Reference yield:

: 123219-41-0
(2R,3S,4R,5R)-3-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-2,4-dimethyl-heptanal

: 131681-73-7
(2S,3R,4S,5R,6R,7S,10S,11R,12R,13R)-1,11-di-O-benzyl-13-O-(tert-butyldimethylsilyl)-2,4,6,8,10,12-hexamethyl-3,5-O-isopropylidene-7-(thiophenoxy)-8(E)-pentadecene-1,3,5,6,11,13-hexol

Guidance literature:: Multi-step reaction with 4 steps

1: 95 percent / tetrahydrofuran / 72 h / 22 °C

2: 95 percent / DIBAL / toluene / 0.25 h / -10 °C

3: 98 percent / pyridine, n-Bu₃P / 22 °C

4: 1.) n-BuLi, TMEDA / 1.) hexane, -40 deg C, 30 min, 2.) THF, HMPA, -78 deg C, 2 min

With pyridine; n-butyllithium; N,N,N,N,-tetramethylethylenediamine; tributylphosphine; diisobutylaluminium hydride; In tetrahydrofuran; toluene;
DOI:10.1021/ja00003a026

Reference yield:

: 106357-31-7
(2S,3S,4R)-1-benzyloxy-2,4-dimethylhex-5-ene-3-ol

: 131681-73-7
(2S,3R,4S,5R,6R,7S,10S,11R,12R,13R)-1,11-di-O-benzyl-13-O-(tert-butyldimethylsilyl)-2,4,6,8,10,12-hexamethyl-3,5-O-isopropylidene-7-(thiophenoxy)-8(E)-pentadecene-1,3,5,6,11,13-hexol

Guidance literature:: Multi-step reaction with 7 steps

1: 98 percent / imidazole / dimethylformamide / 48 h / 60 °C

2: 1.) ozone, 2.) Ph₃P / 1.) CH₂Cl₂, -78 deg C, 2.) from -78 deg C to RT

3: 61 percent / diethyl ether / 2 h / 22 °C

4: 95 percent / (n-Bu)4NF / tetrahydrofuran / 15 h / 22 °C

5: 97 percent / p-toluenesulfonic acid / CH₂Cl₂ / 22 °C

6: 1.) ozone, 2.) Ph₃P / 1.) CH₂Cl₂, -78 deg C, 2.) from -78 deg C to RT

7: 1.) n-BuLi, TMEDA / 1.) hexane, -40 deg C, 30 min, 2.) THF, HMPA, -78 deg C, 2 min

With 1H-imidazole; n-butyllithium; N,N,N,N,-tetramethylethylenediamine; tetrabutyl ammonium fluoride; toluene-4-sulfonic acid; ozone; triphenylphosphine; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ja00003a026