(2R,3R)-3-Benzyloxycarbonylamino-4-(tert-butyl-dimethyl-silanyloxy)-2-iodo-butyric acid benzyl ester

Base Information

Chemical Name:(2R,3R)-3-Benzyloxycarbonylamino-4-(tert-butyl-dimethyl-silanyloxy)-2-iodo-butyric acid benzyl ester
CAS No.:574005-84-8
Molecular Formula:C₂₅H₃₄INO₅Si
Molecular Weight:583.539
Hs Code.:

Synonyms:(2R,3R)-3-Benzyloxycarbonylamino-4-(tert-butyl-dimethyl-silanyloxy)-2-iodo-butyric acid benzyl ester

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Chemical Property of (2R,3R)-3-Benzyloxycarbonylamino-4-(tert-butyl-dimethyl-silanyloxy)-2-iodo-butyric acid benzyl ester

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Technology Process of (2R,3R)-3-Benzyloxycarbonylamino-4-(tert-butyl-dimethyl-silanyloxy)-2-iodo-butyric acid benzyl ester

There total 6 articles about (2R,3R)-3-Benzyloxycarbonylamino-4-(tert-butyl-dimethyl-silanyloxy)-2-iodo-butyric acid benzyl 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: 93.0%

: 574005-82-6
3-benzyloxycarbonylamino-4-(tert-butyl-dimethyl-silanyloxy)-butyric acid benzyl ester

: 574005-84-8
(2R,3R)-3-Benzyloxycarbonylamino-4-(tert-butyl-dimethyl-silanyloxy)-2-iodo-butyric acid benzyl ester

Guidance literature:: 3-benzyloxycarbonylamino-4-(tert-butyl-dimethyl-silanyloxy)-butyric acid benzyl ester; With lithium hexamethyldisilazane; In tetrahydrofuran; toluene; at -20 ℃; for 0.75h;

With iodine; In tetrahydrofuran; toluene; at -30 ℃; for 1h;
DOI:10.1055/s-2003-38733

Reference yield:

: 1152-61-0
N-Cbz-L-Asp

: 574005-84-8
(2R,3R)-3-Benzyloxycarbonylamino-4-(tert-butyl-dimethyl-silanyloxy)-2-iodo-butyric acid benzyl ester

Guidance literature:: Multi-step reaction with 6 steps

1.1: 98 percent / Ac₂O / 0.02 h / microwave irradiation

2.1: NaBH₄ / tetrahydrofuran / 16 h / 20 °C

3.1: aq. CsCO₃ / acetone / 3 h / 20 °C

4.1: imidazole / dimethylformamide / 16 h / 20 °C

5.1: Et₃N / acetone / 16 h / 20 °C

6.1: LiHMDS / tetrahydrofuran; toluene / 0.75 h / -20 °C

6.2: 93 percent / I₂ / tetrahydrofuran; toluene / 1 h / -30 °C

With 1H-imidazole; sodium tetrahydroborate; acetic anhydride; triethylamine; lithium hexamethyldisilazane; In tetrahydrofuran; N,N-dimethyl-formamide; acetone; toluene;
DOI:10.1055/s-2003-38733

Reference yield:

: 87219-29-2
benzyl (3S)-5-oxotetrahydro-3-furanylcarbamate

: 574005-84-8
(2R,3R)-3-Benzyloxycarbonylamino-4-(tert-butyl-dimethyl-silanyloxy)-2-iodo-butyric acid benzyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: aq. CsCO₃ / acetone / 3 h / 20 °C

2.1: imidazole / dimethylformamide / 16 h / 20 °C

3.1: Et₃N / acetone / 16 h / 20 °C

4.1: LiHMDS / tetrahydrofuran; toluene / 0.75 h / -20 °C

4.2: 93 percent / I₂ / tetrahydrofuran; toluene / 1 h / -30 °C

With 1H-imidazole; triethylamine; lithium hexamethyldisilazane; In tetrahydrofuran; N,N-dimethyl-formamide; acetone; toluene;
DOI:10.1055/s-2003-38733