[2-tert-butoxycarbonylamino-3-(tert-butyl-diphenyl-silanyloxy)-propionylamino]-acetic acid allyl ester

Base Information

• Chemical Name: [2-tert-butoxycarbonylamino-3-(tert-butyl-diphenyl-silanyloxy)-propionylamino]-acetic acid allyl ester
• CAS No.: 500734-26-9
• Molecular Formula: C₂₉H₄₀N₂O₆Si
• Molecular Weight: 540.732

Synonyms:[2-tert-butoxycarbonylamino-3-(tert-butyl-diphenyl-silanyloxy)-propionylamino]-acetic acid allyl ester

Chemical Property of [2-tert-butoxycarbonylamino-3-(tert-butyl-diphenyl-silanyloxy)-propionylamino]-acetic acid allyl ester

Chemical Property:

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Technology Process of [2-tert-butoxycarbonylamino-3-(tert-butyl-diphenyl-silanyloxy)-propionylamino]-acetic acid allyl ester

There total 2 articles about [2-tert-butoxycarbonylamino-3-(tert-butyl-diphenyl-silanyloxy)-propionylamino]-acetic acid allyl 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: 85.0%

tert-butylchlorodiphenylsilane (58479-61-1) + Boc-D-Ser-Gly-OAllyl (500734-28-1) → [2-tert-butoxycarbonylamino-3-(tert-butyl-diphenyl-silanyloxy)-propionylamino]-acetic acid allyl ester (500734-26-9)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 20 ℃; for 7h;

DOI:10.1016/S0040-4020(02)01224-3

Reference yield:

(R)-N-tert-butoxycarbonyl serine (3262-72-4,3850-40-6,6368-20-3,90582-28-8,84311-18-2) → [2-tert-butoxycarbonylamino-3-(tert-butyl-diphenyl-silanyloxy)-propionylamino]-acetic acid allyl ester (500734-26-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 56 percent / diethyl phosphorocyanidate; triethylamine / dimethylformamide / 0 - 20 °C

2: 85 percent / triethylamine; DMAP / CH₂Cl₂ / 7 h / 20 °C

With dmap; diethyl cyanophosphonate; triethylamine; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(02)01224-3

Reference yield:

[2-tert-butoxycarbonylamino-3-(tert-butyl-diphenyl-silanyloxy)-propionylamino]-acetic acid allyl ester (500734-26-9) → [2-amino-3-(tert-butyl-diphenyl-silanyloxy)-propionylamino]-acetic acid allyl ester; hydrochloride

Guidance literature:

With hydrogenchloride; In 1,4-dioxane; water; at 20 ℃; for 0.5h;

DOI:10.1016/S0040-4020(02)01224-3

upstream raw materials:

tert-butylchlorodiphenylsilane

Boc-D-Ser-Gly-OAllyl

(R)-N-tert-butoxycarbonyl serine

Downstream raw materials:

[2S,8R,11S,15S]-8-(tert-butyldiphenylsilanyloxymethyl)-15-(4,4-dichloropentyl)-11-(1-hydroxy-1-methyl-ethyl)-2-isopropyl-14,14-dimethyl-12,16-dioxa-20-thia-3,6,9,21-tetraaza-bicyclo[16.2.1]heneicosa-1⁽²¹⁾,18-diene-4,7,10,13,17-pentaone

2-(1-tert-butoxycarbonylamino-2-methyl-propyl)-thiazole-4-carboxylic acid 1-(1-{1-[1-(allyloxycarbonylmethyl-carbamoyl)-2-(tert-butyl-diphenyl-silanyloxy)-ethylcarbamoyl]-2-hydroxy-2-methyl-propoxycarbonyl}-1-methyl-ethyl)-5,5-dichloro-hexyl ester

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