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Cas Database

205491-17-4

205491-17-4

Identification

  • Product Name:Toluene-4-sulfonic acid (S)-2-tert-butoxycarbonylamino-4-(tert-butyl-diphenyl-silanyloxy)-butyl ester

  • CAS Number: 205491-17-4

  • EINECS:

  • Molecular Weight:597.848

  • Molecular Formula: C32H43NO6SSi

  • HS Code:

  • Mol File:205491-17-4.mol

Synonyms:Toluene-4-sulfonic acid (S)-2-tert-butoxycarbonylamino-4-(tert-butyl-diphenyl-silanyloxy)-butyl ester

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Relevant articles and documentsAll total 1 Articles be found

Novel route to the synthesis of hydroxylated pyrrolidine derivatives via the intramolecular reaction of γ-aminoallylstannane with aldehyde. Total synthesis of (+)-preussin

Kadota, Isao,Saya, Shioko,Yamamoto, Yoshinori

, p. 335 - 348 (2007/10/03)

The thermal cyclization of γ-aminoallylstannane (8) having an aldehyde group gave β-hydroxypyrrolidine derivative (9a) as a sole product. This methodology was applied successfully to the total synthesis of (+)-preussin.

Process route upstream and downstream products

Process route

p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

(S)-tert-butyl (4-((tert-butyldiphenylsilyl)oxy)-1-hydroxybutan-2-yl)carbamate
205491-16-3

(S)-tert-butyl (4-((tert-butyldiphenylsilyl)oxy)-1-hydroxybutan-2-yl)carbamate

Toluene-4-sulfonic acid (S)-2-tert-butoxycarbonylamino-4-(tert-butyl-diphenyl-silanyloxy)-butyl ester
205491-17-4

Toluene-4-sulfonic acid (S)-2-tert-butoxycarbonylamino-4-(tert-butyl-diphenyl-silanyloxy)-butyl ester

Conditions
Conditions Yield
With dmap; triethylamine; Ambient temperature;
86%
di-<i>tert</i>-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

Toluene-4-sulfonic acid (S)-2-tert-butoxycarbonylamino-4-(tert-butyl-diphenyl-silanyloxy)-butyl ester
205491-17-4

Toluene-4-sulfonic acid (S)-2-tert-butoxycarbonylamino-4-(tert-butyl-diphenyl-silanyloxy)-butyl ester

Conditions
Conditions Yield
Multi-step reaction with 7 steps
1: 95 percent / 0.5M aq.Na2CO3 / dioxane / Ambient temperature
2: 1.) N-hydroxysuccinimide, DCC; 2.) NaBH4 / 1.) CH2Cl2, r.t., 3 h; 2.) THF, EtOH, 0 deg C, 15 min
3: p-TsOH / CH2Cl2 / Ambient temperature
4: LiAlH4 / diethyl ether / 0.33 h / 0 °C
5: imidazole / CH2Cl2 / Ambient temperature
6: 94 percent / PdCl2(MeCN)2 / acetonitrile / Heating
7: 86 percent / Et3N, DMAP / Ambient temperature
With 1H-imidazole; dmap; dichloro bis(acetonitrile) palladium(II); sodium tetrahydroborate; 1-hydroxy-pyrrolidine-2,5-dione; lithium aluminium tetrahydride; sodium carbonate; toluene-4-sulfonic acid; triethylamine; dicyclohexyl-carbodiimide; In 1,4-dioxane; diethyl ether; dichloromethane; acetonitrile;
(3S)-3-[(tert-butoxycarbonyl)amino]-4-hydroxybutanoic acid methyl ester
136703-59-8

(3S)-3-[(tert-butoxycarbonyl)amino]-4-hydroxybutanoic acid methyl ester

Toluene-4-sulfonic acid (S)-2-tert-butoxycarbonylamino-4-(tert-butyl-diphenyl-silanyloxy)-butyl ester
205491-17-4

Toluene-4-sulfonic acid (S)-2-tert-butoxycarbonylamino-4-(tert-butyl-diphenyl-silanyloxy)-butyl ester

Conditions
Conditions Yield
Multi-step reaction with 5 steps
1: p-TsOH / CH2Cl2 / Ambient temperature
2: LiAlH4 / diethyl ether / 0.33 h / 0 °C
3: imidazole / CH2Cl2 / Ambient temperature
4: 94 percent / PdCl2(MeCN)2 / acetonitrile / Heating
5: 86 percent / Et3N, DMAP / Ambient temperature
With 1H-imidazole; dmap; dichloro bis(acetonitrile) palladium(II); lithium aluminium tetrahydride; toluene-4-sulfonic acid; triethylamine; In diethyl ether; dichloromethane; acetonitrile;
(4S)-2,2-dimethyl-4-(2-hydroxyethyl)oxazolidine-3-carboxylic acid tert-butyl ester
147959-18-0

(4S)-2,2-dimethyl-4-(2-hydroxyethyl)oxazolidine-3-carboxylic acid tert-butyl ester

Toluene-4-sulfonic acid (S)-2-tert-butoxycarbonylamino-4-(tert-butyl-diphenyl-silanyloxy)-butyl ester
205491-17-4

Toluene-4-sulfonic acid (S)-2-tert-butoxycarbonylamino-4-(tert-butyl-diphenyl-silanyloxy)-butyl ester

Conditions
Conditions Yield
Multi-step reaction with 3 steps
1: imidazole / CH2Cl2 / Ambient temperature
2: 94 percent / PdCl2(MeCN)2 / acetonitrile / Heating
3: 86 percent / Et3N, DMAP / Ambient temperature
With 1H-imidazole; dmap; dichloro bis(acetonitrile) palladium(II); triethylamine; In dichloromethane; acetonitrile;
methyl [(4S)-3-(tert-butoxycarbonyl)-2,2-dimethyl-1,3-oxazolidin-4-yl]ethanoate
205491-14-1

methyl [(4S)-3-(tert-butoxycarbonyl)-2,2-dimethyl-1,3-oxazolidin-4-yl]ethanoate

Toluene-4-sulfonic acid (S)-2-tert-butoxycarbonylamino-4-(tert-butyl-diphenyl-silanyloxy)-butyl ester
205491-17-4

Toluene-4-sulfonic acid (S)-2-tert-butoxycarbonylamino-4-(tert-butyl-diphenyl-silanyloxy)-butyl ester

Conditions
Conditions Yield
Multi-step reaction with 4 steps
1: LiAlH4 / diethyl ether / 0.33 h / 0 °C
2: imidazole / CH2Cl2 / Ambient temperature
3: 94 percent / PdCl2(MeCN)2 / acetonitrile / Heating
4: 86 percent / Et3N, DMAP / Ambient temperature
With 1H-imidazole; dmap; dichloro bis(acetonitrile) palladium(II); lithium aluminium tetrahydride; triethylamine; In diethyl ether; dichloromethane; acetonitrile;
(S)-4-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester
205491-15-2

(S)-4-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

Toluene-4-sulfonic acid (S)-2-tert-butoxycarbonylamino-4-(tert-butyl-diphenyl-silanyloxy)-butyl ester
205491-17-4

Toluene-4-sulfonic acid (S)-2-tert-butoxycarbonylamino-4-(tert-butyl-diphenyl-silanyloxy)-butyl ester

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: 94 percent / PdCl2(MeCN)2 / acetonitrile / Heating
2: 86 percent / Et3N, DMAP / Ambient temperature
With dmap; dichloro bis(acetonitrile) palladium(II); triethylamine; In acetonitrile;
Toluene-4-sulfonic acid (S)-2-tert-butoxycarbonylamino-4-(tert-butyl-diphenyl-silanyloxy)-butyl ester
205491-17-4

Toluene-4-sulfonic acid (S)-2-tert-butoxycarbonylamino-4-(tert-butyl-diphenyl-silanyloxy)-butyl ester

Conditions
Conditions Yield
Multi-step reaction with 9 steps
1: 92 percent / CuBr*SMe2 / diethyl ether / 2 h / -35 °C
2: 91 percent / KH / tetrahydrofuran / Ambient temperature
3: 97 percent / TBAF / tetrahydrofuran / Ambient temperature
5: 1.) O3; 2.) Me2S / 1.) MeOH, -78 deg C; 2.) r.t., overnight
6: 99 percent / diethyl ether; tetrahydrofuran / 2 h / -78 °C
7: 1.) 1,1'-thiocarbonyldiimidazole; 2.) n-Bu3SnH, AIBN / 1.) toluene, reflux, 2 h; 2.) toluene, 90 deg C, 40 min
8: 98 percent / TBAF / tetrahydrofuran / Ambient temperature
9: 68 percent / LiAlH4 / tetrahydrofuran / 4 h / Heating
With lithium aluminium tetrahydride; copper(I) bromide dimethylsulfide complex; dimethylsulfide; 2,2'-azobis(isobutyronitrile); tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; potassium hydride; ozone; 1,1'-Thiocarbonyldiimidazole; In tetrahydrofuran; diethyl ether;
octyllithium
3314-49-6

octyllithium

Toluene-4-sulfonic acid (S)-2-tert-butoxycarbonylamino-4-(tert-butyl-diphenyl-silanyloxy)-butyl ester
205491-17-4

Toluene-4-sulfonic acid (S)-2-tert-butoxycarbonylamino-4-(tert-butyl-diphenyl-silanyloxy)-butyl ester

{(R)-1-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-decyl}-carbamic acid tert-butyl ester
205491-09-4

{(R)-1-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-decyl}-carbamic acid tert-butyl ester

Conditions
Conditions Yield
With copper(I) bromide dimethylsulfide complex; In diethyl ether; at -35 ℃; for 2h;
92%
Toluene-4-sulfonic acid (S)-2-tert-butoxycarbonylamino-4-(tert-butyl-diphenyl-silanyloxy)-butyl ester
205491-17-4

Toluene-4-sulfonic acid (S)-2-tert-butoxycarbonylamino-4-(tert-butyl-diphenyl-silanyloxy)-butyl ester

tert-butyl (2S,3S,5R)-2-benzyl-3-hydroxy-5-nonylpyrrolidine-1-carboxylate
158527-21-0

tert-butyl (2S,3S,5R)-2-benzyl-3-hydroxy-5-nonylpyrrolidine-1-carboxylate

Conditions
Conditions Yield
Multi-step reaction with 8 steps
1: 92 percent / CuBr*SMe2 / diethyl ether / 2 h / -35 °C
2: 91 percent / KH / tetrahydrofuran / Ambient temperature
3: 97 percent / TBAF / tetrahydrofuran / Ambient temperature
5: 1.) O3; 2.) Me2S / 1.) MeOH, -78 deg C; 2.) r.t., overnight
6: 99 percent / diethyl ether; tetrahydrofuran / 2 h / -78 °C
7: 1.) 1,1'-thiocarbonyldiimidazole; 2.) n-Bu3SnH, AIBN / 1.) toluene, reflux, 2 h; 2.) toluene, 90 deg C, 40 min
8: 98 percent / TBAF / tetrahydrofuran / Ambient temperature
With copper(I) bromide dimethylsulfide complex; dimethylsulfide; 2,2'-azobis(isobutyronitrile); tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; potassium hydride; ozone; 1,1'-Thiocarbonyldiimidazole; In tetrahydrofuran; diethyl ether;
Toluene-4-sulfonic acid (S)-2-tert-butoxycarbonylamino-4-(tert-butyl-diphenyl-silanyloxy)-butyl ester
205491-17-4

Toluene-4-sulfonic acid (S)-2-tert-butoxycarbonylamino-4-(tert-butyl-diphenyl-silanyloxy)-butyl ester

(-)-(2S,3S,5R)-2-benzyl-3-(tert-butyldimethylsilyloxy)-5-nonylpyrrolidine-1-carboxylic acid tert-butyl ester
175550-96-6

(-)-(2S,3S,5R)-2-benzyl-3-(tert-butyldimethylsilyloxy)-5-nonylpyrrolidine-1-carboxylic acid tert-butyl ester

Conditions
Conditions Yield
Multi-step reaction with 7 steps
1: 92 percent / CuBr*SMe2 / diethyl ether / 2 h / -35 °C
2: 91 percent / KH / tetrahydrofuran / Ambient temperature
3: 97 percent / TBAF / tetrahydrofuran / Ambient temperature
5: 1.) O3; 2.) Me2S / 1.) MeOH, -78 deg C; 2.) r.t., overnight
6: 99 percent / diethyl ether; tetrahydrofuran / 2 h / -78 °C
7: 1.) 1,1'-thiocarbonyldiimidazole; 2.) n-Bu3SnH, AIBN / 1.) toluene, reflux, 2 h; 2.) toluene, 90 deg C, 40 min
With copper(I) bromide dimethylsulfide complex; dimethylsulfide; 2,2'-azobis(isobutyronitrile); tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; potassium hydride; ozone; 1,1'-Thiocarbonyldiimidazole; In tetrahydrofuran; diethyl ether;

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