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

Base Information

• Chemical Name: (E)-(2S,3R,4S,5S,14R)-4-Benzyloxy-2-tert-butoxycarbonylamino-5,14-bis-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-icos-6-enoic acid
• CAS No.: 181210-38-8
• Molecular Formula: C₄₄H₈₁NO₈Si₂
• Molecular Weight: 808.3
• Mol file: 181210-38-8.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 23 articles about (E)-(2S,3R,4S,5S,14R)-4-Benzyloxy-2-tert-butoxycarbonylamino-5,14-bis-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-icos-6-enoic acid 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:

(3R)-3-(methoxymethoxy)-1-nonanol (181211-26-7) → (E)-(2S,3R,4S,5S,14R)-4-Benzyloxy-2-tert-butoxycarbonylamino-5,14-bis-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-icos-6-enoic acid (181210-38-8)

Guidance literature:

Multi-step reaction with 14 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: CH₂Cl₂ / 10 h / Ambient temperature

14: aq. LiOH / tetrahydrofuran / 10 h / 0 °C

With 1H-imidazole; hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; lithium hydroxide; lithium aluminium tetrahydride; n-butyllithium; formic acid; oxalyl dichloride; carbon tetrabromide; hydrogen; 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:

heptanal (111-71-7) → (E)-(2S,3R,4S,5S,14R)-4-Benzyloxy-2-tert-butoxycarbonylamino-5,14-bis-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-icos-6-enoic acid (181210-38-8)

Guidance literature:

Multi-step reaction with 17 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: CH₂Cl₂ / 10 h / Ambient temperature

17: aq. LiOH / tetrahydrofuran / 10 h / 0 °C

With 1H-imidazole; hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; lithium hydroxide; 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; 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:

S-ethyl (R)-3-hydroxynonanethioate (181211-25-6) → (E)-(2S,3R,4S,5S,14R)-4-Benzyloxy-2-tert-butoxycarbonylamino-5,14-bis-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-icos-6-enoic acid (181210-38-8)

Guidance literature:

Multi-step reaction with 16 steps

1: diisopropylethylamine / CH₂Cl₂ / 10 h / Ambient temperature

2: LiAlH₄ / tetrahydrofuran / 1.5 h / Ambient temperature

3: CBr₄, Ph₃P / CH₂Cl₂ / 0.5 h

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, 4 h

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

6: CBr₄, Ph₃P / CH₂Cl₂ / 0.5 h / 0 °C

7: 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

8: 96 percent / conc. aq. HCl / methanol / 0.5 h / 60 °C

9: 85 percent / Et₃N, DMAP / CH₂Cl₂ / 1 h / 0 °C

10: LiAlH₄ / tetrahydrofuran / 1 h / Heating

11: imidazole / dimethylformamide / 10 h / Ambient temperature

12: 85 percent / 98percent aq. formic acid / diethyl ether / 0.5 h / 0 °C

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

14: 1.) LDA, 2.) ZnCl₂

15: CH₂Cl₂ / 10 h / Ambient temperature

16: aq. LiOH / tetrahydrofuran / 10 h / 0 °C

With 1H-imidazole; hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; lithium hydroxide; lithium aluminium tetrahydride; n-butyllithium; formic acid; oxalyl dichloride; carbon tetrabromide; hydrogen; 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

upstream raw materials:

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

heptanal

di-tert-butyl dicarbonate

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

Downstream raw materials:

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