(E)-(2S,3R,4S,5S,14R)-2-Amino-4-benzyloxy-5,14-bis-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-icos-6-enoic acid ethyl ester

Base Information

• Chemical Name: (E)-(2S,3R,4S,5S,14R)-2-Amino-4-benzyloxy-5,14-bis-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-icos-6-enoic acid ethyl ester
• CAS No.: 181210-37-7
• Molecular Formula: C₄₁H₇₇NO₆Si₂
• Molecular Weight: 736.236
• Mol file: 181210-37-7.mol

Synonyms:(E)-(2S,3R,4S,5S,14R)-2-Amino-4-benzyloxy-5,14-bis-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-icos-6-enoic acid ethyl ester

Chemical Property of (E)-(2S,3R,4S,5S,14R)-2-Amino-4-benzyloxy-5,14-bis-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-icos-6-enoic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-(2S,3R,4S,5S,14R)-2-Amino-4-benzyloxy-5,14-bis-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-icos-6-enoic acid ethyl ester

There total 19 articles about (E)-(2S,3R,4S,5S,14R)-2-Amino-4-benzyloxy-5,14-bis-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-icos-6-enoic acid ethyl ester 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:

heptanal (111-71-7) → (E)-(2S,3R,4S,5S,14R)-2-Amino-4-benzyloxy-5,14-bis-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-icos-6-enoic acid ethyl ester (181210-37-7)

Guidance literature:

Multi-step reaction with 16 steps

1: Sn(OTf)2, SnO, (S)-1-methyl-2-<(N-1-naphthylamino)methyl>pyrrolidine / CH₂Cl₂; various solvent(s) / 1 h / -78 °C

2: diisopropylethylamine / CH₂Cl₂ / 10 h / Ambient temperature

3: LiAlH₄ / tetrahydrofuran / 1.5 h / Ambient temperature

4: CBr₄, Ph₃P / CH₂Cl₂ / 0.5 h

5: 1.) n-BuLi, 2.) HMPA / 1.) THF, hexane, -78 deg C, 15 min, 2.) THF, hexane, a.) -78 deg C, 10 min, b.) 0 deg C, 4 h

6: H₂ / 10percent Pd/C / ethanol / 20 h / 760 Torr

7: CBr₄, Ph₃P / CH₂Cl₂ / 0.5 h / 0 °C

8: 1.) n-BuLi, 2.) HMPA / 1.) THF, hexane, -78 deg C, 15 min, 2.) THF, hexane, a.) -78 deg C, 10 min, b.) 0 deg C, 10 h

9: 96 percent / conc. aq. HCl / methanol / 0.5 h / 60 °C

10: 85 percent / Et₃N, DMAP / CH₂Cl₂ / 1 h / 0 °C

11: LiAlH₄ / tetrahydrofuran / 1 h / Heating

12: imidazole / dimethylformamide / 10 h / Ambient temperature

13: 85 percent / 98percent aq. formic acid / diethyl ether / 0.5 h / 0 °C

14: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, from -78 to -50 deg C, 70 min, 2.) CH₂Cl₂, 0 deg C, 20 min

15: 1.) LDA, 2.) ZnCl₂

16: TsOH

With 1H-imidazole; hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; lithium aluminium tetrahydride; tin(II) trifluoromethanesulfonate; n-butyllithium; formic acid; oxalyl dichloride; carbon tetrabromide; hydrogen; tin(II) oxide; (2S)-1-methyl-2-<(N-1-naphthylamino)methyl>pyrrolidine; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; zinc(II) chloride; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ja9730829

Reference yield:

(3R)-3-(methoxymethoxy)-1-nonanol (181211-26-7) → (E)-(2S,3R,4S,5S,14R)-2-Amino-4-benzyloxy-5,14-bis-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-icos-6-enoic acid ethyl ester (181210-37-7)

Guidance literature:

Multi-step reaction with 13 steps

1: CBr₄, Ph₃P / CH₂Cl₂ / 0.5 h

2: 1.) n-BuLi, 2.) HMPA / 1.) THF, hexane, -78 deg C, 15 min, 2.) THF, hexane, a.) -78 deg C, 10 min, b.) 0 deg C, 4 h

3: H₂ / 10percent Pd/C / ethanol / 20 h / 760 Torr

4: CBr₄, Ph₃P / CH₂Cl₂ / 0.5 h / 0 °C

5: 1.) n-BuLi, 2.) HMPA / 1.) THF, hexane, -78 deg C, 15 min, 2.) THF, hexane, a.) -78 deg C, 10 min, b.) 0 deg C, 10 h

6: 96 percent / conc. aq. HCl / methanol / 0.5 h / 60 °C

7: 85 percent / Et₃N, DMAP / CH₂Cl₂ / 1 h / 0 °C

8: LiAlH₄ / tetrahydrofuran / 1 h / Heating

9: imidazole / dimethylformamide / 10 h / Ambient temperature

10: 85 percent / 98percent aq. formic acid / diethyl ether / 0.5 h / 0 °C

11: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, from -78 to -50 deg C, 70 min, 2.) CH₂Cl₂, 0 deg C, 20 min

12: 1.) LDA, 2.) ZnCl₂

13: TsOH

With 1H-imidazole; hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; lithium aluminium tetrahydride; n-butyllithium; formic acid; oxalyl dichloride; carbon tetrabromide; hydrogen; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; triphenylphosphine; zinc(II) chloride; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ja9730829

Reference yield:

1-bromo-(3R)-3-(methoxymethoxy)nonane (181211-28-9) → (E)-(2S,3R,4S,5S,14R)-2-Amino-4-benzyloxy-5,14-bis-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-icos-6-enoic acid ethyl ester (181210-37-7)

Guidance literature:

Multi-step reaction with 12 steps

1: 1.) n-BuLi, 2.) HMPA / 1.) THF, hexane, -78 deg C, 15 min, 2.) THF, hexane, a.) -78 deg C, 10 min, b.) 0 deg C, 4 h

2: H₂ / 10percent Pd/C / ethanol / 20 h / 760 Torr

3: CBr₄, Ph₃P / CH₂Cl₂ / 0.5 h / 0 °C

4: 1.) n-BuLi, 2.) HMPA / 1.) THF, hexane, -78 deg C, 15 min, 2.) THF, hexane, a.) -78 deg C, 10 min, b.) 0 deg C, 10 h

5: 96 percent / conc. aq. HCl / methanol / 0.5 h / 60 °C

6: 85 percent / Et₃N, DMAP / CH₂Cl₂ / 1 h / 0 °C

7: LiAlH₄ / tetrahydrofuran / 1 h / Heating

8: imidazole / dimethylformamide / 10 h / Ambient temperature

9: 85 percent / 98percent aq. formic acid / diethyl ether / 0.5 h / 0 °C

10: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, from -78 to -50 deg C, 70 min, 2.) CH₂Cl₂, 0 deg C, 20 min

11: 1.) LDA, 2.) ZnCl₂

12: TsOH

With 1H-imidazole; hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; lithium aluminium tetrahydride; n-butyllithium; formic acid; oxalyl dichloride; carbon tetrabromide; hydrogen; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; triphenylphosphine; zinc(II) chloride; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ja9730829

upstream raw materials:

(1R,1S,2S,3S,4'R,12R)-2-benzyloxy-3,12-di(tert-butyldimethylsiloxy)-1-(3',6'-diethoxy-4'-(isopropyl)-1'H,4'H-2',5'-diazyl)-octadec-4-ene-1-ol

heptanal

(4S,5S)-5-benzyloxy-4-ethynyl-2,2-dimethyl-1,3-dioxane

(2S,3S,12R)-2-benzyloxy-3,12-di(tert-butyldimethylsiloxy)-1-(4-methoxyphenyldiphenylmethoxy)-4-octadecene

Downstream raw materials:

ethyl (2S,3R,4S,5S,14R)-4-benzyloxy-2-(tert-butoxycarbonylamino)-5,14-di(tert-butyldimethylsiloxy)-3-hydroxyeicos-6-enoate

(E)-(2S,3R,4S,5S,14R)-4-Benzyloxy-2-tert-butoxycarbonylamino-5,14-bis-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-icos-6-enoic acid

(2S,3R,4R,5S,14R)-4-benzyloxy-2-(tert-butoxycarbonylamino)-3,5,14-trihydroxyeicos-6-enoic acid