Silane, (1,1-dimethylethyl)[[(1S,2E)-9-(2-hexyl-1,3-dioxolan-2-yl)-1-[(1S)-2-[(4- methoxyphenyl)diphenylmethoxy]-1-(phenylmethoxy)ethyl]-2-nonenyl]oxy ]dimethyl-

Base Information

• Chemical Name: Silane, (1,1-dimethylethyl)[[(1S,2E)-9-(2-hexyl-1,3-dioxolan-2-yl)-1-[(1S)-2-[(4- methoxyphenyl)diphenylmethoxy]-1-(phenylmethoxy)ethyl]-2-nonenyl]oxy ]dimethyl-
• CAS No.: 189246-61-5
• Molecular Formula: C53H74O6Si
• Molecular Weight: 835.252
• Mol file: 189246-61-5.mol

Synonyms:

Chemical Property of Silane, (1,1-dimethylethyl)[[(1S,2E)-9-(2-hexyl-1,3-dioxolan-2-yl)-1-[(1S)-2-[(4- methoxyphenyl)diphenylmethoxy]-1-(phenylmethoxy)ethyl]-2-nonenyl]oxy ]dimethyl-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Silane, (1,1-dimethylethyl)[[(1S,2E)-9-(2-hexyl-1,3-dioxolan-2-yl)-1-[(1S)-2-[(4- methoxyphenyl)diphenylmethoxy]-1-(phenylmethoxy)ethyl]-2-nonenyl]oxy ]dimethyl-

There total 24 articles about Silane, (1,1-dimethylethyl)[[(1S,2E)-9-(2-hexyl-1,3-dioxolan-2-yl)-1-[(1S)-2-[(4- methoxyphenyl)diphenylmethoxy]-1-(phenylmethoxy)ethyl]-2-nonenyl]oxy ]dimethyl- 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: 91.0%

tert-butyldimethylsilyl chloride (18162-48-6) + (16S,17S)-17-benzyloxy-16,18-dihydroxyoctadec-14-yne-7-one ethylene acetal (189246-60-4) + mono-4-methoxytrityl chloride (14470-28-1) → (16S,17S)-17-benzyloxy-16-(tert-butyldimethylsiloxy)-18-(4-methoxyphenyldiphenylmethoxy)-octadec-14-ene-7-one ethylene acetal (189246-61-5)

Guidance literature:

(16S,17S)-17-benzyloxy-16,18-dihydroxyoctadec-14-yne-7-one ethylene acetal; mono-4-methoxytrityl chloride; With dmap; triethylamine; In dichloromethane; at 0 ℃; for 1h;

With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 - 20 ℃; for 1h;

tert-butyldimethylsilyl chloride; With 1H-imidazole; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 10h;

DOI:10.1016/S0040-4020(98)00484-0

Reference yield:

(3RS)-ethyl-3-hydroxynonanethioate (189246-52-4) → (16S,17S)-17-benzyloxy-16-(tert-butyldimethylsiloxy)-18-(4-methoxyphenyldiphenylmethoxy)-octadec-14-ene-7-one ethylene acetal (189246-61-5)

Guidance literature:

Multi-step reaction with 14 steps

1.1: diisopropylethylamine / CH₂Cl₂ / 10 h / 0 - 20 °C

2.1: LAH / tetrahydrofuran / 1.5 h / 0 - 20 °C

3.1: CBr₄; Ph₃P / CH₂Cl₂ / 0.5 h / 0 °C

4.1: n-BuLi; HMPA / tetrahydrofuran; hexane / 4.5 h / -78 - 0 °C

5.1: H₂ / Pd/C / ethanol / 20 h / 760 Torr

6.1: CBr₄; Ph₃P / CH₂Cl₂ / 0.5 h / 0 °C

7.1: 100 percent / HCl / methanol / 3 h / 50 °C

8.1: 97 percent / Et₃N / CH₂Cl₂ / 0.25 h / 0 - 20 °C

9.1: 89 percent / n-BuLi; HMPA / tetrahydrofuran; hexane / 10.5 h / -78 - 0 °C

10.1: 100 percent / TBAF / tetrahydrofuran / 1.5 h / 20 °C

11.1: 87 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / 2 h / -78 - 0 °C

12.1: 100 percent / HCl / tetrahydrofuran / 0.5 h / 20 °C

13.1: 94 percent / TMSOTf / CH₂Cl₂ / 1 h / 0 °C

14.1: Et₃N; DMAP / CH₂Cl₂ / 1 h / 0 °C

14.2: LAH / tetrahydrofuran / 1 h / 0 - 20 °C

14.3: 91 percent / imidazole / dimethylformamide / 10 h / 0 - 20 °C

With hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; carbon tetrabromide; trimethylsilyl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; hydrogen; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; 1.1: Etherification / 2.1: Reduction / 3.1: Bromination / 4.1: Addition / 5.1: Reduction / 6.1: Bromination / 7.1: Elimination / 8.1: Etherification / 9.1: Addition / 10.1: Elimination / 11.1: Swern oxidation / 12.1: Elimination / 13.1: Etherification / 14.1: Etherification / 14.2: Reduction / 14.3: Etherification;

DOI:10.1016/S0040-4020(98)00484-0

Reference yield:

1-bromo-3-(methoxymethoxy)nonane → (16S,17S)-17-benzyloxy-16-(tert-butyldimethylsiloxy)-18-(4-methoxyphenyldiphenylmethoxy)-octadec-14-ene-7-one ethylene acetal (189246-61-5)

Guidance literature:

Multi-step reaction with 11 steps

1.1: n-BuLi; HMPA / tetrahydrofuran; hexane / 4.5 h / -78 - 0 °C

2.1: H₂ / Pd/C / ethanol / 20 h / 760 Torr

3.1: CBr₄; Ph₃P / CH₂Cl₂ / 0.5 h / 0 °C

4.1: 100 percent / HCl / methanol / 3 h / 50 °C

5.1: 97 percent / Et₃N / CH₂Cl₂ / 0.25 h / 0 - 20 °C

6.1: 89 percent / n-BuLi; HMPA / tetrahydrofuran; hexane / 10.5 h / -78 - 0 °C

7.1: 100 percent / TBAF / tetrahydrofuran / 1.5 h / 20 °C

8.1: 87 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / 2 h / -78 - 0 °C

9.1: 100 percent / HCl / tetrahydrofuran / 0.5 h / 20 °C

10.1: 94 percent / TMSOTf / CH₂Cl₂ / 1 h / 0 °C

11.1: Et₃N; DMAP / CH₂Cl₂ / 1 h / 0 °C

11.2: LAH / tetrahydrofuran / 1 h / 0 - 20 °C

11.3: 91 percent / imidazole / dimethylformamide / 10 h / 0 - 20 °C

With hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; n-butyllithium; oxalyl dichloride; carbon tetrabromide; trimethylsilyl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; hydrogen; dimethyl sulfoxide; triethylamine; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; 1.1: Addition / 2.1: Reduction / 3.1: Bromination / 4.1: Elimination / 5.1: Etherification / 6.1: Addition / 7.1: Elimination / 8.1: Swern oxidation / 9.1: Elimination / 10.1: Etherification / 11.1: Etherification / 11.2: Reduction / 11.3: Etherification;

DOI:10.1016/S0040-4020(98)00484-0

upstream raw materials:

tert-butyldimethylsilyl chloride

(16S,17S)-17-benzyloxy-16,18-dihydroxyoctadec-14-yne-7-one ethylene acetal

mono-4-methoxytrityl chloride

heptanal

Downstream raw materials:

sphingofungin F

(2R,3S)-2-benzyloxy-3-(tert-butyldimethylsiloxy)-12-oxooctadec-4-enal

(2S,3S,4R,5S)-2-amino-4-benzyloxy-2-methyl-3,5-dihydroxy-14-oxoeicos-6-enoic acid

(1'S,4'S,16S,17S,18R)-17-benzyloxy-18-(3',6'-diethoxy-1',4'-dimethyl-4'H-2',5'-diazyl)-16,18-dihydroxyoctadec-14-ene-7-one

Refernces

• 1、 Kobayashi, Shu,Furuta, Takayuki. "Use of heterocycles as chiral ligands and auxiliaries in asymmetric syntheses of sphingosine, sphingofungins B and F". . p. 10275 - 10294. Retrieved 2007/10/03.