6-tert-butoxycarbonylamino-hexanoic acid 3-O-({2-[3-(2-{2-[2-(2-amino-ethoxy)-ethoxy]-ethoxy}-ethoxy)-propyonylamino]-ethoxy}-benzyloxy-phosphoryloxy)-2-O-(tert-butyl-dimethylsilyl)-sn-glyceryl ester

Base Information

• Chemical Name: 6-tert-butoxycarbonylamino-hexanoic acid 3-O-({2-[3-(2-{2-[2-(2-amino-ethoxy)-ethoxy]-ethoxy}-ethoxy)-propyonylamino]-ethoxy}-benzyloxy-phosphoryloxy)-2-O-(tert-butyl-dimethylsilyl)-sn-glyceryl ester
• CAS No.: 888959-52-2
• Molecular Formula: C₄₈H₈₀N₃O₁₆PSi
• Molecular Weight: 1014.23

Synonyms:6-tert-butoxycarbonylamino-hexanoic acid 3-O-({2-[3-(2-{2-[2-(2-amino-ethoxy)-ethoxy]-ethoxy}-ethoxy)-propyonylamino]-ethoxy}-benzyloxy-phosphoryloxy)-2-O-(tert-butyl-dimethylsilyl)-sn-glyceryl ester

Chemical Property of 6-tert-butoxycarbonylamino-hexanoic acid 3-O-({2-[3-(2-{2-[2-(2-amino-ethoxy)-ethoxy]-ethoxy}-ethoxy)-propyonylamino]-ethoxy}-benzyloxy-phosphoryloxy)-2-O-(tert-butyl-dimethylsilyl)-sn-glyceryl ester

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Technology Process of 6-tert-butoxycarbonylamino-hexanoic acid 3-O-({2-[3-(2-{2-[2-(2-amino-ethoxy)-ethoxy]-ethoxy}-ethoxy)-propyonylamino]-ethoxy}-benzyloxy-phosphoryloxy)-2-O-(tert-butyl-dimethylsilyl)-sn-glyceryl ester

There total 8 articles about 6-tert-butoxycarbonylamino-hexanoic acid 3-O-({2-[3-(2-{2-[2-(2-amino-ethoxy)-ethoxy]-ethoxy}-ethoxy)-propyonylamino]-ethoxy}-benzyloxy-phosphoryloxy)-2-O-(tert-butyl-dimethylsilyl)-sn-glyceryl 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:

6-(tert-butoxycarbonylamino)hexanoic acid (6404-29-1) → 6-tert-butoxycarbonylamino-hexanoic acid 3-O-({2-[3-(2-{2-[2-(2-amino-ethoxy)-ethoxy]-ethoxy}-ethoxy)-propyonylamino]-ethoxy}-benzyloxy-phosphoryloxy)-2-O-(tert-butyl-dimethylsilyl)-sn-glyceryl ester (888959-52-2)

Guidance literature:

Multi-step reaction with 6 steps

1: 49 percent / DCC; DMAP / CH₂Cl₂ / 4 °C

2: 90 percent / imidazole / 18 h / 20 °C

3: 97 percent / DDQ; water / CH₂Cl₂ / 20 °C

4: 85 percent / 1H-tetrazole / CH₂Cl₂ / cooling

5: 1H-tetrazole / CH₂Cl₂ / 1.5 h / 20 °C

6: 85.3 mg / m-chloroperbenzoic acid / CH₂Cl₂ / -40 - 20 °C

With 1H-imidazole; 1H-tetrazole; dmap; water; 3-chloro-benzenecarboperoxoic acid; dicyclohexyl-carbodiimide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane;

DOI:10.1021/ol060414i

Reference yield:

6-tert-butoxycarbonylamino-hexanoic acid 3-(benzyloxy-{2-[3-(2-{2-[2-(2-benzyloxycarbonylamino-ethoxy)-ethoxy]-ethoxy}-ethoxy)-propionylamino]-ethoxy}-phosphanyloxy)-2-(tert-butyl-dimethyl-silanyloxy)-propyl ester → 6-tert-butoxycarbonylamino-hexanoic acid 3-O-({2-[3-(2-{2-[2-(2-amino-ethoxy)-ethoxy]-ethoxy}-ethoxy)-propyonylamino]-ethoxy}-benzyloxy-phosphoryloxy)-2-O-(tert-butyl-dimethylsilyl)-sn-glyceryl ester (888959-52-2)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at -40 - 20 ℃;

DOI:10.1021/ol060414i

Reference yield:

3-oxo-1-phenyl-2,7,10,13,16-pentaoxa-4-azanonadecan-19-oic acid (756526-00-8,1334177-88-6) → 6-tert-butoxycarbonylamino-hexanoic acid 3-O-({2-[3-(2-{2-[2-(2-amino-ethoxy)-ethoxy]-ethoxy}-ethoxy)-propyonylamino]-ethoxy}-benzyloxy-phosphoryloxy)-2-O-(tert-butyl-dimethylsilyl)-sn-glyceryl ester (888959-52-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: diisopropylcarbodiimide; HOBt / CH₂Cl₂; dimethylformamide / 0.25 h

1.2: 74 percent / CH₂Cl₂; dimethylformamide / 4 h

2.1: 1H-tetrazole / CH₂Cl₂ / 1.5 h / 20 °C

3.1: 85.3 mg / m-chloroperbenzoic acid / CH₂Cl₂ / -40 - 20 °C

With 1H-tetrazole; benzotriazol-1-ol; 3-chloro-benzenecarboperoxoic acid; diisopropyl-carbodiimide; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ol060414i

upstream raw materials:

3-oxo-1-phenyl-2,7,10,13,16-pentaoxa-4-azanonadecan-19-oic acid

1-O-[6-(N-Boc-amino)hexanoyl]-2-O-tert-butyldimethylsilyl-sn-glycerol

1-O-[6-(N-Boc-amino)-hexanoyl]-3-O-(4-methoxybenzyl)-sn-glycerol

{2-[2-(2-{2-[2-(2-hydroxy-ethylcarbamoyl)-ethoxy]-ethoxy}-ethoxy)-ethoxy]-ethyl}-carbamic acid benzyl ester

Downstream raw materials:

6-tert-butoxycarbonylamino-hexanoic acid 2-(tert-butyl-dimethyl-silanyloxy)-3-{[2-(3-{2-[2-(2-{2-[4-(4-dimethylamino-phenylazo)-benzoylamino]-ethoxy}-ethoxy)-ethoxy]-ethoxy}-propionylamino)-ethoxy]-hydroxy-phosphoryloxy}-propyl ester

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