2-[(N-benzyloxycarbonyl)amino]ethyl 4,6-dideoxy-4-(3-hydroxy-3-methylbutanamido)-2-O-methyl-β-D-glucopyranoside

Base Information

Chemical Name:2-[(N-benzyloxycarbonyl)amino]ethyl 4,6-dideoxy-4-(3-hydroxy-3-methylbutanamido)-2-O-methyl-β-D-glucopyranoside
CAS No.:1042430-64-7
Molecular Formula:C₂₂H₃₄N₂O₈
Molecular Weight:454.521
Hs Code.:

Synonyms:2-[(N-benzyloxycarbonyl)amino]ethyl 4,6-dideoxy-4-(3-hydroxy-3-methylbutanamido)-2-O-methyl-β-D-glucopyranoside

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Chemical Property of 2-[(N-benzyloxycarbonyl)amino]ethyl 4,6-dideoxy-4-(3-hydroxy-3-methylbutanamido)-2-O-methyl-β-D-glucopyranoside

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Technology Process of 2-[(N-benzyloxycarbonyl)amino]ethyl 4,6-dideoxy-4-(3-hydroxy-3-methylbutanamido)-2-O-methyl-β-D-glucopyranoside

There total 12 articles about 2-[(N-benzyloxycarbonyl)amino]ethyl 4,6-dideoxy-4-(3-hydroxy-3-methylbutanamido)-2-O-methyl-β-D-glucopyranoside 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: 65.0%

: 1042430-63-6
N-benzyloxycarbonylaminoethyl 3-O-benzoyl-4,6-dideoxy-4-(3-hydroxy-3-methylbutanamido)-2-O-methyl-β-D-glucopyranoside

: 1042430-64-7
2-[(N-benzyloxycarbonyl)amino]ethyl 4,6-dideoxy-4-(3-hydroxy-3-methylbutanamido)-2-O-methyl-β-D-glucopyranoside

Guidance literature:: With methanol; sodium methylate; at 20 ℃; for 1h;
DOI:10.1016/j.carres.2007.11.030

Reference yield:

: 1314864-92-0
β-hydroxyisovaleric acid succinimidyl ester

: 2-[(N-benzyloxycarbonyl)amino]ethanol 4-amino-4,6-dideoxy-2-O-methyl-β-D-glucopyranoside

: 1042430-64-7
2-[(N-benzyloxycarbonyl)amino]ethyl 4,6-dideoxy-4-(3-hydroxy-3-methylbutanamido)-2-O-methyl-β-D-glucopyranoside

Guidance literature:: With N-ethyl-N,N-diisopropylamine; In acetonitrile; at 20 ℃; for 4h; Inert atmosphere;
DOI:10.1021/jo200340q

Reference yield:

: 77987-49-6
benzyl 2-hydroxyethylcarbamate

: 1042430-64-7
2-[(N-benzyloxycarbonyl)amino]ethyl 4,6-dideoxy-4-(3-hydroxy-3-methylbutanamido)-2-O-methyl-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 6 steps

1.1: ytterbium(III) triflate / toluene / 0.5 h / Molecular sieve; Inert atmosphere

1.2: 4 h / 100 °C / Inert atmosphere

2.1: silver(l) oxide / dichloromethane / 1 h / 20 °C

2.2: 20 °C

3.1: sodium periodate; ruthenium(III) trichloride hydrate / tetrachloromethane; water; acetonitrile / 2 h / 0 °C

4.1: sodium azide / N,N-dimethyl-formamide / 2 h / 60 °C

4.2: 1 h / 20 °C

5.1: sodium tetrahydroborate; nickel(II) chloride hexahydrate / ethanol; dichloromethane / 1 h / 20 °C

6.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 4 h / 20 °C / Inert atmosphere

With sodium tetrahydroborate; sodium periodate; sodium azide; nickel(II) chloride hexahydrate; ruthenium(III) trichloride hydrate; N-ethyl-N,N-diisopropylamine; silver(l) oxide; ytterbium(III) triflate; In tetrachloromethane; ethanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile;
DOI:10.1021/jo200340q