benzyl (2S,5R)-2-benzyloxycarbonylamino-5-triisopropylsilyloxymethyl-5,6-dihydroxyhexanoate

Base Information

Chemical Name:benzyl (2S,5R)-2-benzyloxycarbonylamino-5-triisopropylsilyloxymethyl-5,6-dihydroxyhexanoate
CAS No.:796869-82-4
Molecular Formula:C₃₁H₄₇NO₇Si
Molecular Weight:573.802
Hs Code.:

Synonyms:benzyl (2S,5R)-2-benzyloxycarbonylamino-5-triisopropylsilyloxymethyl-5,6-dihydroxyhexanoate

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Chemical Property of benzyl (2S,5R)-2-benzyloxycarbonylamino-5-triisopropylsilyloxymethyl-5,6-dihydroxyhexanoate

Chemical Property:

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Technology Process of benzyl (2S,5R)-2-benzyloxycarbonylamino-5-triisopropylsilyloxymethyl-5,6-dihydroxyhexanoate

There total 1 articles about benzyl (2S,5R)-2-benzyloxycarbonylamino-5-triisopropylsilyloxymethyl-5,6-dihydroxyhexanoate 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:

: 796869-79-9
benzyl (S)-2-benzyloxycarbonylamino-5-triisopropylsilyloxymethyl-5-hexenoate

: 796869-82-4
benzyl (2S,5R)-2-benzyloxycarbonylamino-5-triisopropylsilyloxymethyl-5,6-dihydroxyhexanoate

: 796869-97-1
benzyl (2S,5S)-2-benzyloxycarbonylamino-5-triisopropylsilyloxymethyl-5,6-dihydroxyhexanoate

Guidance literature:: With 1,4-bis(9-O-dihydroquinidine)phthalazine; In water; tert-butyl alcohol; at 0 ℃; for 72h; Further Variations:; Reagents; Product distribution;
DOI:10.1055/s-2007-983785

Reference yield: 89.0%

: 796869-82-4
benzyl (2S,5R)-2-benzyloxycarbonylamino-5-triisopropylsilyloxymethyl-5,6-dihydroxyhexanoate

: 796869-88-0
1-benzyl hydrogen (2S,5S)-2-benzyloxycarbonylamino-5-hydroxy-5-[(triisopropylsilyloxy)methyl]hexanedioate

Guidance literature:: With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; sodium chlorite; In acetonitrile; at 20 ℃; for 12h;
DOI:10.1016/j.tetlet.2004.09.033

Reference yield:

: 796869-82-4
benzyl (2S,5R)-2-benzyloxycarbonylamino-5-triisopropylsilyloxymethyl-5,6-dihydroxyhexanoate

: (S)-2-Amino-4-((S)-3-hydroxy-2-oxo-azetidin-3-yl)-butyric acid benzyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: 89 percent / TEMPO; aq. NaClO; NaClO₂ / acetonitrile / 12 h / 20 °C

2: 95 percent / NaHCO₃; HOBt; EDCI / 12 h / 0 - 20 °C

3: 86 percent / TBAF / tetrahydrofuran / 1 h / 0 °C

4: 91 percent / Et₃N / CHCl₃ / 12 h / 20 °C

5: 88 percent / 2,6-lutidine / CH₂Cl₂ / 2 h / 20 °C

6: 11 percent / KHMDS / tetrahydrofuran / 24 h / -78 - 0 °C

7: TBAF / tetrahydrofuran / 0 °C

8: H₂ / Raney-Ni / aq. methanol

With 2,6-dimethylpyridine; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; sodium chlorite; tetrabutyl ammonium fluoride; hydrogen; potassium hexamethylsilazane; sodium hydrogencarbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; nickel; In tetrahydrofuran; methanol; dichloromethane; chloroform; acetonitrile;
DOI:10.1016/j.tetlet.2004.09.033