phenyl 2-amino-N-benzyl-2N,3O-carbamoyl-2-deoxy-5,6-O-isopropylidene-α-D-lyxofuranosyl sulfone

Base Information

Chemical Name:phenyl 2-amino-N-benzyl-2N,3O-carbamoyl-2-deoxy-5,6-O-isopropylidene-α-D-lyxofuranosyl sulfone
CAS No.:220458-75-3
Molecular Formula:C₂₃H₂₅NO₇S
Molecular Weight:459.52
Hs Code.:

Synonyms:phenyl 2-amino-N-benzyl-2N,3O-carbamoyl-2-deoxy-5,6-O-isopropylidene-α-D-lyxofuranosyl sulfone

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Chemical Property of phenyl 2-amino-N-benzyl-2N,3O-carbamoyl-2-deoxy-5,6-O-isopropylidene-α-D-lyxofuranosyl sulfone

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Technology Process of phenyl 2-amino-N-benzyl-2N,3O-carbamoyl-2-deoxy-5,6-O-isopropylidene-α-D-lyxofuranosyl sulfone

There total 3 articles about phenyl 2-amino-N-benzyl-2N,3O-carbamoyl-2-deoxy-5,6-O-isopropylidene-α-D-lyxofuranosyl sulfone 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: 85.0%

: 3173-56-6
benzyl isothiocyanate

: 220458-74-2
(2S,3R)-5-Benzenesulfonyl-2-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,3-dihydro-furan-3-ol

: 220458-75-3
phenyl 2-amino-N-benzyl-2N,3O-carbamoyl-2-deoxy-5,6-O-isopropylidene-α-D-lyxofuranosyl sulfone

Guidance literature:: With potassium tert-butylate; In tetrahydrofuran; 0 deg C, 1 h then r.t., 20 h;
DOI:10.3987/com-98-8292

Reference yield:

: 91510-85-9
phenyl 2,3;5,6-di-O-isopropylidene-1-thio-α-D-mannofuranoside

: 220458-75-3
phenyl 2-amino-N-benzyl-2N,3O-carbamoyl-2-deoxy-5,6-O-isopropylidene-α-D-lyxofuranosyl sulfone

Guidance literature:: Multi-step reaction with 3 steps

1: 80 percent / sat. aq. NaHCO₃, m-CPBA / CH₂Cl₂ / 20 h / Ambient temperature

2: 86 percent / BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide / -78 deg C, 1 h then r.t., 2 h

3: 85 percent / potassium t-butoxide / tetrahydrofuran / 0 deg C, 1 h then r.t., 20 h

With n-butyllithium; potassium tert-butylate; sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane;
DOI:10.3987/com-98-8292

Reference yield:

: 220458-81-1
(3aS,4R,6R,6aS)-4-Benzenesulfonyl-6-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole

: 220458-75-3
phenyl 2-amino-N-benzyl-2N,3O-carbamoyl-2-deoxy-5,6-O-isopropylidene-α-D-lyxofuranosyl sulfone

Guidance literature:: Multi-step reaction with 2 steps

1: 86 percent / BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide / -78 deg C, 1 h then r.t., 2 h

2: 85 percent / potassium t-butoxide / tetrahydrofuran / 0 deg C, 1 h then r.t., 20 h

With n-butyllithium; potassium tert-butylate; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide;
DOI:10.3987/com-98-8292