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

Base Information

• Chemical Name: 1-benzyl hydrogen (2S,5S)-2-benzyloxycarbonylamino-5-hydroxy-5-[(triisopropylsilyloxy)methyl]hexanedioate
• CAS No.: 796869-88-0
• Molecular Formula: C₃₁H₄₅NO₈Si
• Molecular Weight: 587.786
• Mol file: 796869-88-0.mol

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

Chemical Property of 1-benzyl hydrogen (2S,5S)-2-benzyloxycarbonylamino-5-hydroxy-5-[(triisopropylsilyloxy)methyl]hexanedioate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-benzyl hydrogen (2S,5S)-2-benzyloxycarbonylamino-5-hydroxy-5-[(triisopropylsilyloxy)methyl]hexanedioate

There total 2 articles about 1-benzyl hydrogen (2S,5S)-2-benzyloxycarbonylamino-5-hydroxy-5-[(triisopropylsilyloxy)methyl]hexanedioate 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: 89.0%

benzyl (2S,5R)-2-benzyloxycarbonylamino-5-triisopropylsilyloxymethyl-5,6-dihydroxyhexanoate (796869-82-4) → 1-benzyl hydrogen (2S,5S)-2-benzyloxycarbonylamino-5-hydroxy-5-[(triisopropylsilyloxy)methyl]hexanedioate (796869-88-0)

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:

benzyl (2S)-2-benzyloxycarbonylamino-5-triisopropylsilyloxymethyl-5,6-dihydroxyhexanoate → 1-benzyl hydrogen (2S,5S)-2-benzyloxycarbonylamino-5-hydroxy-5-[(triisopropylsilyloxy)methyl]hexanedioate (796869-88-0) + 1-benzyl hydrogen (2S,5R)-2-benzyloxycarbonylamino-5-hydroxy-5-[(triisopropylsilyloxy)methyl]hexanedioate (956007-33-3)

Guidance literature:

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; sodium chlorite; In phosphate buffer; acetonitrile; at 20 ℃; for 12h; pH=6.7; Title compound not separated from byproducts.;

DOI:10.1055/s-2007-983785

Reference yield:

1-benzyl hydrogen (2S,5S)-2-benzyloxycarbonylamino-5-hydroxy-5-[(triisopropylsilyloxy)methyl]hexanedioate (796869-88-0) → benzyl (2S,5S)-5-benzyloxycarbamoyl-2-benzyloxycarbonylamino-5,6-dihydroxyhexanoate (796869-89-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 95 percent / NaHCO₃; HOBt; EDCI / 12 h / 0 - 20 °C

2: 86 percent / TBAF / tetrahydrofuran / 1 h / 0 °C

With tetrabutyl ammonium fluoride; sodium hydrogencarbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran;

DOI:10.1016/j.tetlet.2004.09.033

upstream raw materials:

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

Downstream raw materials:

(3S,3'S)-1-benzyloxy-3-(3'-benzyloxycarbonyl-3'-benzyloxycarbonylaminopropyl)-3-hydroxy-2-azetidinone

(3S,3'S)-1-benzyloxy-3-(3'-benzyloxycarbonylamino-3'-carboxypropyl)-3-tert-butyldimethylsilyloxy-2-azetidinone

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

benzyl (2S,5S)-5-benzyloxycarbamoyl-2-benzyloxycarbonylamino-5-hydroxy-6-methylsulfonyloxyhexanoate