(3R,4S)-4-Benzyloxycarbonylamino-8-(2,3-bis-benzyloxy-benzoylamino)-3-(tert-butyl-dimethyl-silanyloxy)-octanoic acid

Base Information

Chemical Name:(3R,4S)-4-Benzyloxycarbonylamino-8-(2,3-bis-benzyloxy-benzoylamino)-3-(tert-butyl-dimethyl-silanyloxy)-octanoic acid
CAS No.:167275-74-3
Molecular Formula:C₄₃H₅₄N₂O₈Si
Molecular Weight:754.996
Hs Code.:

Synonyms:(3R,4S)-4-Benzyloxycarbonylamino-8-(2,3-bis-benzyloxy-benzoylamino)-3-(tert-butyl-dimethyl-silanyloxy)-octanoic acid

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Chemical Property of (3R,4S)-4-Benzyloxycarbonylamino-8-(2,3-bis-benzyloxy-benzoylamino)-3-(tert-butyl-dimethyl-silanyloxy)-octanoic acid

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Technology Process of (3R,4S)-4-Benzyloxycarbonylamino-8-(2,3-bis-benzyloxy-benzoylamino)-3-(tert-butyl-dimethyl-silanyloxy)-octanoic acid

There total 11 articles about (3R,4S)-4-Benzyloxycarbonylamino-8-(2,3-bis-benzyloxy-benzoylamino)-3-(tert-butyl-dimethyl-silanyloxy)-octanoic 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:

: 167275-72-1
(S)-4-Benzyloxycarbonylamino-8-tert-butoxycarbonylamino-3-oxo-octanoic acid ethyl ester

: 167275-74-3
(3R,4S)-4-Benzyloxycarbonylamino-8-(2,3-bis-benzyloxy-benzoylamino)-3-(tert-butyl-dimethyl-silanyloxy)-octanoic acid

Guidance literature:: Multi-step reaction with 5 steps

1: 66 percent / NaBH₄ / ethanol; tetrahydrofuran / 1.5 h / -78 °C

2: aq. HCl / dioxane / 1.) 0 deg C, 1 h, 2.) r.t., 45 min

3: Et₃N, diethyl phosphorocyanidate / dimethylformamide / 1.) 0 deg C, 4 h, 2.) 0 deg C to r.t., 13 h

4: aq. LiOH / tetrahydrofuran / 3 h / 0 °C

5: imidazole / dimethylformamide / 1.) 0 deg C, 15 min, 2.) 0 deg C to r.t., 17.5 h

With 1H-imidazole; hydrogenchloride; lithium hydroxide; sodium tetrahydroborate; diethyl cyanophosphonate; triethylamine; In tetrahydrofuran; 1,4-dioxane; ethanol; N,N-dimethyl-formamide;
DOI:10.1055/s-1998-5937

Reference yield:

: 167275-82-3
(3R,4S)-4-Benzyloxycarbonylamino-8-(2,3-bis-benzyloxy-benzoylamino)-3-hydroxy-octanoic acid ethyl ester

: 167275-74-3
(3R,4S)-4-Benzyloxycarbonylamino-8-(2,3-bis-benzyloxy-benzoylamino)-3-(tert-butyl-dimethyl-silanyloxy)-octanoic acid

Guidance literature:: Multi-step reaction with 2 steps

1: aq. LiOH / tetrahydrofuran / 3 h / 0 °C

2: imidazole / dimethylformamide / 1.) 0 deg C, 15 min, 2.) 0 deg C to r.t., 17.5 h

With 1H-imidazole; lithium hydroxide; In tetrahydrofuran; N,N-dimethyl-formamide;
DOI:10.1055/s-1998-5937

Reference yield:

: 74272-78-9
2,3-dibenzyloxybenzoic acid

: 167275-74-3
(3R,4S)-4-Benzyloxycarbonylamino-8-(2,3-bis-benzyloxy-benzoylamino)-3-(tert-butyl-dimethyl-silanyloxy)-octanoic acid

Guidance literature:: Multi-step reaction with 3 steps

1: Et₃N, diethyl phosphorocyanidate / dimethylformamide / 1.) 0 deg C, 4 h, 2.) 0 deg C to r.t., 13 h

2: aq. LiOH / tetrahydrofuran / 3 h / 0 °C

3: imidazole / dimethylformamide / 1.) 0 deg C, 15 min, 2.) 0 deg C to r.t., 17.5 h

With 1H-imidazole; lithium hydroxide; diethyl cyanophosphonate; triethylamine; In tetrahydrofuran; N,N-dimethyl-formamide;
DOI:10.1055/s-1998-5937