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

Base Information

Chemical Name:(E)-(2S,3R,4S,5S)-4-Benzyloxy-2-tert-butoxycarbonylamino-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-icos-6-enoic acid ethyl ester
CAS No.:181211-22-3
Molecular Formula:C₄₀H₇₁NO₇Si
Molecular Weight:706.092
Hs Code.:

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

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

Chemical Property:

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

There total 11 articles about (E)-(2S,3R,4S,5S)-4-Benzyloxy-2-tert-butoxycarbonylamino-5-(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:

: 765-09-3
1-bromotridecane

: 181211-22-3
(E)-(2S,3R,4S,5S)-4-Benzyloxy-2-tert-butoxycarbonylamino-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-icos-6-enoic acid ethyl ester

Guidance literature:: Multi-step reaction with 9 steps

1: 1.) BuLi, 2.) HMPA / 1.) THF, 2.) THF, from -78 deg C to RT

2: 96 percent / 3 N aq. HCl / tetrahydrofuran / Ambient temperature

3: Et₃N, DMAP / CH₂Cl₂ / 0 °C

4: LiAlH₄ / tetrahydrofuran / Heating

5: imidazole / dimethylformamide

6: 83 percent / HCOOH / diethyl ether

7: 95 percent / (COCl)2, DMSO, Et₃N / CH₂Cl₂ / -50 °C

8: 1.) LDA, 2.) ZnCl₂

9: CH₂Cl₂

With 1H-imidazole; hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; lithium aluminium tetrahydride; n-butyllithium; formic acid; oxalyl dichloride; dimethyl sulfoxide; triethylamine; zinc(II) chloride; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ja9730829

Reference yield:

: 181434-86-6
(4S,5S)-5-benzyloxy-4-ethynyl-2,2-dimethyl-1,3-dioxane

: 181211-22-3
(E)-(2S,3R,4S,5S)-4-Benzyloxy-2-tert-butoxycarbonylamino-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-icos-6-enoic acid ethyl ester

Guidance literature:: Multi-step reaction with 9 steps

1: 1.) BuLi, 2.) HMPA / 1.) THF, 2.) THF, from -78 deg C to RT

2: 96 percent / 3 N aq. HCl / tetrahydrofuran / Ambient temperature

3: Et₃N, DMAP / CH₂Cl₂ / 0 °C

4: LiAlH₄ / tetrahydrofuran / Heating

5: imidazole / dimethylformamide

6: 83 percent / HCOOH / diethyl ether

7: 95 percent / (COCl)2, DMSO, Et₃N / CH₂Cl₂ / -50 °C

8: 1.) LDA, 2.) ZnCl₂

9: CH₂Cl₂

With 1H-imidazole; hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; lithium aluminium tetrahydride; n-butyllithium; formic acid; oxalyl dichloride; dimethyl sulfoxide; triethylamine; zinc(II) chloride; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ja9730829

Reference yield:

: 181211-21-2
(E)-(2R,3S)-2-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-octadec-4-enal

: 181211-22-3
(E)-(2S,3R,4S,5S)-4-Benzyloxy-2-tert-butoxycarbonylamino-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-icos-6-enoic acid ethyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 1.) LDA, 2.) ZnCl₂

2: CH₂Cl₂

With zinc(II) chloride; lithium diisopropyl amide; In dichloromethane;
DOI:10.1021/ja9730829