1,2:5,6-di-O-isopropylidene-α-D-glucofuranos-3-O-yl N-[(S)-1-(methoxycarbonyl)-3-methylbutyl]-(S)-α-phenylglycinate

Base Information

• Chemical Name: 1,2:5,6-di-O-isopropylidene-α-D-glucofuranos-3-O-yl N-[(S)-1-(methoxycarbonyl)-3-methylbutyl]-(S)-α-phenylglycinate
• CAS No.: 902778-48-7
• Molecular Formula: C₂₇H₃₉NO₉
• Molecular Weight: 521.608

Synonyms:1,2:5,6-di-O-isopropylidene-α-D-glucofuranos-3-O-yl N-[(S)-1-(methoxycarbonyl)-3-methylbutyl]-(S)-α-phenylglycinate

Chemical Property of 1,2:5,6-di-O-isopropylidene-α-D-glucofuranos-3-O-yl N-[(S)-1-(methoxycarbonyl)-3-methylbutyl]-(S)-α-phenylglycinate

Chemical Property:

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Technology Process of 1,2:5,6-di-O-isopropylidene-α-D-glucofuranos-3-O-yl N-[(S)-1-(methoxycarbonyl)-3-methylbutyl]-(S)-α-phenylglycinate

There total 3 articles about 1,2:5,6-di-O-isopropylidene-α-D-glucofuranos-3-O-yl N-[(S)-1-(methoxycarbonyl)-3-methylbutyl]-(S)-α-phenylglycinate 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: 81.0%

1,2:5,6-di-O-isopropylidene-α-D-glucofuranos-3-O-yl α-bromo-α-phenylacetate (902778-26-1) + (S)-Leu-OMe (2666-93-5) → 1,2:5,6-di-O-isopropylidene-α-D-glucofuranos-3-O-yl N-[(S)-1-(methoxycarbonyl)-3-methylbutyl]-(S)-α-phenylglycinate (902778-48-7)

Guidance literature:

With tetra-(n-butyl)ammonium iodide; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃; for 12h;

DOI:10.1016/j.tet.2006.04.045

Reference yield:

2-bromophenylacetic acid (4870-65-9,31302-84-8) → 1,2:5,6-di-O-isopropylidene-α-D-glucofuranos-3-O-yl N-[(S)-1-(methoxycarbonyl)-3-methylbutyl]-(S)-α-phenylglycinate (902778-48-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 54 percent / DCC; Et₃N; DMAP / CH₂Cl₂ / 3 h / 20 °C

2: 81 percent / ethyldiisopropylamine; tetrabutylammonium iodide / CH₂Cl₂ / 12 h / 20 °C

With dmap; tetra-(n-butyl)ammonium iodide; triethylamine; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; In dichloromethane;

DOI:10.1016/j.tet.2006.04.045

Reference yield:

1,2:5,6-di-O-isopropylidene-α-D-glucofuranose (582-52-5) → 1,2:5,6-di-O-isopropylidene-α-D-glucofuranos-3-O-yl N-[(S)-1-(methoxycarbonyl)-3-methylbutyl]-(S)-α-phenylglycinate (902778-48-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 54 percent / DCC; Et₃N; DMAP / CH₂Cl₂ / 3 h / 20 °C

2: 81 percent / ethyldiisopropylamine; tetrabutylammonium iodide / CH₂Cl₂ / 12 h / 20 °C

With dmap; tetra-(n-butyl)ammonium iodide; triethylamine; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; In dichloromethane;

DOI:10.1016/j.tet.2006.04.045

upstream raw materials:

1,2:5,6-di-O-isopropylidene-α-D-glucofuranos-3-O-yl α-bromo-α-phenylacetate

(S)-Leu-OMe

2-bromophenylacetic acid

1,2:5,6-di-O-isopropylidene-α-D-glucofuranose

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