benzyl (2S,5R)-5-benzyloxycarbamoyl-2-benzyloxycarbonylamino-5-tert-butyldimethylsilyloxy-6-methylsulfonyloxyhexanoate

Base Information

Chemical Name:benzyl (2S,5R)-5-benzyloxycarbamoyl-2-benzyloxycarbonylamino-5-tert-butyldimethylsilyloxy-6-methylsulfonyloxyhexanoate
CAS No.:956007-37-7
Molecular Formula:C₃₆H₄₈N₂O₁₀SSi
Molecular Weight:728.936
Hs Code.:

Synonyms:benzyl (2S,5R)-5-benzyloxycarbamoyl-2-benzyloxycarbonylamino-5-tert-butyldimethylsilyloxy-6-methylsulfonyloxyhexanoate

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Chemical Property of benzyl (2S,5R)-5-benzyloxycarbamoyl-2-benzyloxycarbonylamino-5-tert-butyldimethylsilyloxy-6-methylsulfonyloxyhexanoate

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Technology Process of benzyl (2S,5R)-5-benzyloxycarbamoyl-2-benzyloxycarbonylamino-5-tert-butyldimethylsilyloxy-6-methylsulfonyloxyhexanoate

There total 7 articles about benzyl (2S,5R)-5-benzyloxycarbamoyl-2-benzyloxycarbonylamino-5-tert-butyldimethylsilyloxy-6-methylsulfonyloxyhexanoate 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: 98.0%

: 69739-34-0
t-butyldimethylsiyl triflate

: 956007-36-6
benzyl (2S,5R)-5-benzyloxycarbamoyl-2-benzyloxycarbonylamino-5-hydroxy-6-methylsulfonyloxyhexanoate

: 956007-37-7
benzyl (2S,5R)-5-benzyloxycarbamoyl-2-benzyloxycarbonylamino-5-tert-butyldimethylsilyloxy-6-methylsulfonyloxyhexanoate

Guidance literature:: With 2,6-dimethylpyridine; In dichloromethane; at 20 ℃;
DOI:10.1055/s-2007-983785

Reference yield:

: benzyl (2S)-5-benzyloxycarbamoyl-2-benzyloxycarbonylamino-5,6-dihydroxyhexanoate

: 956007-37-7
benzyl (2S,5R)-5-benzyloxycarbamoyl-2-benzyloxycarbonylamino-5-tert-butyldimethylsilyloxy-6-methylsulfonyloxyhexanoate

Guidance literature:: Multi-step reaction with 2 steps

1: 59 percent / pyridine / CHCl₃ / 6 h / 20 °C

2: 98 percent / 2,6-lutidine / CH₂Cl₂ / 20 °C

With pyridine; 2,6-dimethylpyridine; In dichloromethane; chloroform;
DOI:10.1055/s-2007-983785

Reference yield:

: 2687-43-6
O-benzylhydoxylamine hydrochloride

: 956007-37-7
benzyl (2S,5R)-5-benzyloxycarbamoyl-2-benzyloxycarbonylamino-5-tert-butyldimethylsilyloxy-6-methylsulfonyloxyhexanoate

Guidance literature:: Multi-step reaction with 4 steps

1: NaHCO₃; HOBt; EDCI / 12 h / 0 - 20 °C

2: TBAF / tetrahydrofuran / 1 h / 0 °C

3: Et₃N / CHCl₃ / 12 h / 20 °C

4: 2,6-lutidine / CH₂Cl₂ / 2 h / 20 °C

With 2,6-dimethylpyridine; tetrabutyl ammonium fluoride; sodium hydrogencarbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In tetrahydrofuran; dichloromethane; chloroform;
DOI:10.1016/j.tetlet.2004.09.033