O-benzyl N-2-(5-amino-3-benzyloxy-4-methoxyphenyl)-2-(t-butyldimethylsilyloxy)ethyl carbamate

Base Information

Chemical Name:O-benzyl N-2-(5-amino-3-benzyloxy-4-methoxyphenyl)-2-(t-butyldimethylsilyloxy)ethyl carbamate
CAS No.:312327-28-9
Molecular Formula:C₃₀H₄₀N₂O₅Si
Molecular Weight:536.744
Hs Code.:

Synonyms:O-benzyl N-2-(5-amino-3-benzyloxy-4-methoxyphenyl)-2-(t-butyldimethylsilyloxy)ethyl carbamate

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Chemical Property of O-benzyl N-2-(5-amino-3-benzyloxy-4-methoxyphenyl)-2-(t-butyldimethylsilyloxy)ethyl carbamate

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Technology Process of O-benzyl N-2-(5-amino-3-benzyloxy-4-methoxyphenyl)-2-(t-butyldimethylsilyloxy)ethyl carbamate

There total 7 articles about O-benzyl N-2-(5-amino-3-benzyloxy-4-methoxyphenyl)-2-(t-butyldimethylsilyloxy)ethyl carbamate 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: 97.0%

: 501-53-1,94274-21-2
benzyl chloroformate

: 312327-27-8
2-(5-amino-3-benzyloxy-4-methoxyphenyl)-2-(tert-butyldimethylsilyloxy)ethylamine

: 312327-28-9
O-benzyl N-2-(5-amino-3-benzyloxy-4-methoxyphenyl)-2-(t-butyldimethylsilyloxy)ethyl carbamate

Guidance literature:: With dmap; potassium carbonate; In tetrahydrofuran; at -78 - -30 ℃;
DOI:10.1021/jo001080s

Reference yield:

: 6635-20-7
isonitrovanillin

: 312327-28-9
O-benzyl N-2-(5-amino-3-benzyloxy-4-methoxyphenyl)-2-(t-butyldimethylsilyloxy)ethyl carbamate

Guidance literature:: Multi-step reaction with 7 steps

1: 98 percent / AlCl₃; pyridine / CHCl₃ / 24 h / Heating

2: 93 percent / dimethylformamide / 48 h / 140 °C

3: 92 percent / KOH; benzyltriethylammonium chloride / CHCl₃ / 36 h / 20 °C

4: Amberlyst A-21 ion-exchange resin / tetrahydrofuran / 3 h / 20 °C

5: 1.86 g / 2,6-lutidine / tetrahydrofuran / 2 h / 0 - 20 °C

6: 76 percent / NaBH₄; NiCl₂*6H₂O / methanol; tetrahydrofuran / 25 h / 0 °C

7: 97 percent / DMAP; K₂CO₃ / tetrahydrofuran / -78 - -30 °C

With pyridine; 2,6-dimethylpyridine; dmap; potassium hydroxide; sodium tetrahydroborate; aluminium trichloride; Amberlyst A-21 ion-exchange resin; N-benzyl-N,N,N-triethylammonium chloride; potassium carbonate; nickel dichloride; In tetrahydrofuran; methanol; chloroform; N,N-dimethyl-formamide; 1: ether cleavage / 2: Alkylation / 3: Methylation / 4: Addition / 5: silylation / 6: Reduction / 7: benzyloxycarbonylation;
DOI:10.1021/jo001080s

Reference yield:

: 116313-85-0
3,4-dihydroxy-5-nitrobenzaldehyde

: 312327-28-9
O-benzyl N-2-(5-amino-3-benzyloxy-4-methoxyphenyl)-2-(t-butyldimethylsilyloxy)ethyl carbamate

Guidance literature:: Multi-step reaction with 6 steps

1: 93 percent / dimethylformamide / 48 h / 140 °C

2: 92 percent / KOH; benzyltriethylammonium chloride / CHCl₃ / 36 h / 20 °C

3: Amberlyst A-21 ion-exchange resin / tetrahydrofuran / 3 h / 20 °C

4: 1.86 g / 2,6-lutidine / tetrahydrofuran / 2 h / 0 - 20 °C

5: 76 percent / NaBH₄; NiCl₂*6H₂O / methanol; tetrahydrofuran / 25 h / 0 °C

6: 97 percent / DMAP; K₂CO₃ / tetrahydrofuran / -78 - -30 °C

With 2,6-dimethylpyridine; dmap; potassium hydroxide; sodium tetrahydroborate; Amberlyst A-21 ion-exchange resin; N-benzyl-N,N,N-triethylammonium chloride; potassium carbonate; nickel dichloride; In tetrahydrofuran; methanol; chloroform; N,N-dimethyl-formamide; 1: Alkylation / 2: Methylation / 3: Addition / 4: silylation / 5: Reduction / 6: benzyloxycarbonylation;
DOI:10.1021/jo001080s