erythro-N^4a-((tert-butyloxy)carbonyl)-N^im-(triphenylmethyl)-β-hydroxy-L-histidine methyl ester

Base Information

• Chemical Name: erythro-N^4a-((tert-butyloxy)carbonyl)-N^im-(triphenylmethyl)-β-hydroxy-L-histidine methyl ester
• CAS No.: 160054-24-0
• Molecular Formula: C₃₁H₃₃N₃O₅
• Molecular Weight: 527.62

Synonyms:erythro-N^4a-((tert-butyloxy)carbonyl)-N^im-(triphenylmethyl)-β-hydroxy-L-histidine methyl ester

Chemical Property of erythro-N^4a-((tert-butyloxy)carbonyl)-N^im-(triphenylmethyl)-β-hydroxy-L-histidine methyl ester

Chemical Property:

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Technology Process of erythro-N^4a-((tert-butyloxy)carbonyl)-N^im-(triphenylmethyl)-β-hydroxy-L-histidine methyl ester

There total 5 articles about erythro-N^4a-((tert-butyloxy)carbonyl)-N^im-(triphenylmethyl)-β-hydroxy-L-histidine methyl 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: 100.0%

di-tert-butyl dicarbonate (24424-99-5) + erythro-N?-Triphenylmethyl-β-hydroxy-L-histidinmethylester (142582-33-0) → erythro-N4a-((tert-butyloxy)carbonyl)-Nim-(triphenylmethyl)-β-hydroxy-L-histidine methyl ester (160054-24-0)

Guidance literature:

In tetrahydrofuran; water; at 23 ℃; for 1.5h;

DOI:10.1021/ja00092a011

Reference yield:

(4R,3'R,2'R)-3-<2'-bromo-3'-hydroxy-(N-(triphenylmethyl)imidazol-4''-yl)propanoyl>-4-isopropyl-2-oxazolidinone (121895-45-2) → erythro-N4a-((tert-butyloxy)carbonyl)-Nim-(triphenylmethyl)-β-hydroxy-L-histidine methyl ester (160054-24-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 94 percent / NaN₃ / dimethylformamide / 1.5 h / 45 °C

2: 60 percent / MeONa / 0.08 h / 0 °C

3: 84 percent / H₂S / methanol; H₂O / 48 h / 25 °C

4: 100 percent / tetrahydrofuran; H₂O / 1.5 h / 23 °C

With sodium azide; hydrogen sulfide; sodium methylate; In tetrahydrofuran; methanol; water; N,N-dimethyl-formamide;

DOI:10.1021/ja00092a011

Reference yield:

(2S,3R)-2-Azido-3-hydroxy-3-(1-trityl-1H-imidazol-4-yl)-propionic acid methyl ester (141243-34-7) → erythro-N4a-((tert-butyloxy)carbonyl)-Nim-(triphenylmethyl)-β-hydroxy-L-histidine methyl ester (160054-24-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 84 percent / H₂S / methanol; H₂O / 48 h / 25 °C

2: 100 percent / tetrahydrofuran; H₂O / 1.5 h / 23 °C

With hydrogen sulfide; In tetrahydrofuran; methanol; water;

DOI:10.1021/ja00092a011

upstream raw materials:

di-tert-butyl dicarbonate

erythro-N^?-Triphenylmethyl-β-hydroxy-L-histidinmethylester

(2S,3R)-2-Azido-3-hydroxy-3-(1-trityl-1H-imidazol-4-yl)-propionic acid methyl ester

(4R,3'R,2'R)-3-<2'-bromo-3'-hydroxy-(N-(triphenylmethyl)imidazol-4''-yl)propanoyl>-4-isopropyl-2-oxazolidinone

Downstream raw materials:

3-<2'-(2'''-((N-(4''(R)-((N^α((tert-butyloxy)carbonyl)-N^im(triphenylmethyl)-erythro-β-hydroxy-L-histidyl)amino)-3''(S)-hydroxy-2''-(S)-methylpentanoyl)-L-threonyl)amino)ethyl)-2,4'-bithiazole-4-carboxamido>propyl methyl sulfide

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