(S)-1-[(2R,3R)-3-Benzyloxycarbonyl-3-tert-butoxycarbonylamino-2-(tert-butyl-dimethyl-silanyloxy)-propyl]-azetidine-2-carboxylic acid benzyl ester

Base Information

• Chemical Name: (S)-1-[(2R,3R)-3-Benzyloxycarbonyl-3-tert-butoxycarbonylamino-2-(tert-butyl-dimethyl-silanyloxy)-propyl]-azetidine-2-carboxylic acid benzyl ester
• CAS No.: 105879-55-8
• Molecular Formula: C₃₃H₄₈N₂O₇Si
• Molecular Weight: 612.839

Synonyms:

Chemical Property of (S)-1-[(2R,3R)-3-Benzyloxycarbonyl-3-tert-butoxycarbonylamino-2-(tert-butyl-dimethyl-silanyloxy)-propyl]-azetidine-2-carboxylic acid benzyl ester

Chemical Property:

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Technology Process of (S)-1-[(2R,3R)-3-Benzyloxycarbonyl-3-tert-butoxycarbonylamino-2-(tert-butyl-dimethyl-silanyloxy)-propyl]-azetidine-2-carboxylic acid benzyl ester

There total 16 articles about (S)-1-[(2R,3R)-3-Benzyloxycarbonyl-3-tert-butoxycarbonylamino-2-(tert-butyl-dimethyl-silanyloxy)-propyl]-azetidine-2-carboxylic 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: 58.0%

(S)-1-[(2S,3S)-3-tert-Butoxycarbonylamino-2-(tert-butyl-dimethyl-silanyloxy)-3-methoxycarbonyl-propyl]-azetidine-2-carboxylic acid benzyl ester (131472-72-5) + benzyl alcohol (100-51-6,185532-71-2) → benzyl N-<(2S,2'S,3S)-3'-tert-butoxycarbonylamino-3'-benzyloxycarbonyl-2'-tert-butyldimethylsiloxypropyl>-2-azetidinecarboxylate (105879-55-8)

Guidance literature:

With titanium(IV) isopropylate; at 80 ℃; for 16h;

DOI:10.1016/S0040-4039(00)97800-6

Reference yield: 43.0%

benzyl (2R,3R)-2-tert-butoxycarbonylamino-3-tert-butyldimethylsiloxy-4-oxobutyrate (144704-74-5) + benzyl (S)-2-azetidinecarboxylate p-toluenesulfonate salt (131501-48-9) → benzyl N-<(2S,2'S,3S)-3'-tert-butoxycarbonylamino-3'-benzyloxycarbonyl-2'-tert-butyldimethylsiloxypropyl>-2-azetidinecarboxylate (105879-55-8)

Guidance literature:

With sodium cyanoborohydride; In methanol; for 12h;

DOI:10.1016/S0957-4166(00)86041-3

Reference yield: 28.0%

tert-butyldimethylsilyl chloride (18162-48-6) + (S)-1-(3-Benzyloxycarbonyl-3-tert-butoxycarbonylamino-2-hydroxy-propyl)-azetidine-2-carboxylic acid benzyl ester (105762-95-6,105816-50-0) → benzyl N-<(2S,2'S,3S)-3'-tert-butoxycarbonylamino-3'-benzyloxycarbonyl-2'-tert-butyldimethylsiloxypropyl>-2-azetidinecarboxylate (105879-55-8) + (S)-1-[(2R,3R)-3-Benzyloxycarbonyl-3-tert-butoxycarbonylamino-2-(tert-butyl-dimethyl-silanyloxy)-propyl]-azetidine-2-carboxylic acid benzyl ester (105762-97-8,105879-55-8)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; for 18h; Ambient temperature;

DOI:10.1021/jo00376a102

upstream raw materials:

tert-butyldimethylsilyl chloride

(S)-1-(3-Benzyloxycarbonyl-3-tert-butoxycarbonylamino-2-hydroxy-propyl)-azetidine-2-carboxylic acid benzyl ester

benzyl (2R,3R)-2-tert-butoxycarbonylamino-3-tert-butyldimethylsiloxy-4-oxobutyrate

benzyl (S)-2-azetidinecarboxylate p-toluenesulfonate salt

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