benzyl 4C-[(tert-butoxycarbonyl)amino]methyl-4-deoxy-2-O-isopropyl-α-D-arabinopyranoside

Base Information

Chemical Name:benzyl 4C-[(tert-butoxycarbonyl)amino]methyl-4-deoxy-2-O-isopropyl-α-D-arabinopyranoside
CAS No.:958001-15-5
Molecular Formula:C₂₁H₃₃NO₆
Molecular Weight:395.496
Hs Code.:

Synonyms:benzyl 4C-[(tert-butoxycarbonyl)amino]methyl-4-deoxy-2-O-isopropyl-α-D-arabinopyranoside

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Chemical Property of benzyl 4C-[(tert-butoxycarbonyl)amino]methyl-4-deoxy-2-O-isopropyl-α-D-arabinopyranoside

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Technology Process of benzyl 4C-[(tert-butoxycarbonyl)amino]methyl-4-deoxy-2-O-isopropyl-α-D-arabinopyranoside

There total 3 articles about benzyl 4C-[(tert-butoxycarbonyl)amino]methyl-4-deoxy-2-O-isopropyl-α-D-arabinopyranoside 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: 58.0%

: 24424-99-5
di-tert-butyl dicarbonate

: 478175-78-9
benzyl 4-cyano-4-deoxy-2,3-O-isopropylidene-α-D-arabinoside

: 958001-15-5
benzyl 4C-[(tert-butoxycarbonyl)amino]methyl-4-deoxy-2-O-isopropyl-α-D-arabinopyranoside

Guidance literature:: benzyl 4-cyano-4-deoxy-2,3-O-isopropylidene-α-D-arabinoside; With aluminium hydride; In tetrahydrofuran; at 0 ℃; for 2h;

di-tert-butyl dicarbonate; With sodium hydroxide; In tetrahydrofuran; water; at 20 ℃; for 5h;
DOI:10.1071/CH06241

Reference yield:

: 478175-66-5
benzyl 2,3-O-isopropylidene-β-L-xylopyranoside

: 958001-15-5
benzyl 4C-[(tert-butoxycarbonyl)amino]methyl-4-deoxy-2-O-isopropyl-α-D-arabinopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1.1: 90 percent / lithium bis(trimethylsilyl)amide / tetrahydrofuran / 1 h / -30 - 20 °C

2.1: 80 percent / Bu₄NF / acetonitrile

3.1: AlH₃ / tetrahydrofuran / 2 h / 0 °C

3.2: 58 percent / NaOH / H₂O; tetrahydrofuran / 5 h / 20 °C

With aluminium hydride; tetrabutyl ammonium fluoride; lithium hexamethyldisilazane; In tetrahydrofuran; acetonitrile;
DOI:10.1071/CH06241

Reference yield:

: 478175-76-7
benzyl 4-O-(imidazol-1-ylsulfonyl)-2,3-O-isopropylidene-β-L-xylopyranoside

: 958001-15-5
benzyl 4C-[(tert-butoxycarbonyl)amino]methyl-4-deoxy-2-O-isopropyl-α-D-arabinopyranoside

Guidance literature:: Multi-step reaction with 2 steps

1.1: 80 percent / Bu₄NF / acetonitrile

2.1: AlH₃ / tetrahydrofuran / 2 h / 0 °C

2.2: 58 percent / NaOH / H₂O; tetrahydrofuran / 5 h / 20 °C

With aluminium hydride; tetrabutyl ammonium fluoride; In tetrahydrofuran; acetonitrile;
DOI:10.1071/CH06241