phenyl 2-amino-N-benzyl-2N,3O-carbamoyl-2,5-dideoxy-5-iodo-α-D-lyxofuranosyl sulfone

Base Information

Chemical Name:phenyl 2-amino-N-benzyl-2N,3O-carbamoyl-2,5-dideoxy-5-iodo-α-D-lyxofuranosyl sulfone
CAS No.:220458-82-2
Molecular Formula:C₁₉H₁₈INO₅S
Molecular Weight:499.326
Hs Code.:

Synonyms:phenyl 2-amino-N-benzyl-2N,3O-carbamoyl-2,5-dideoxy-5-iodo-α-D-lyxofuranosyl sulfone

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Chemical Property of phenyl 2-amino-N-benzyl-2N,3O-carbamoyl-2,5-dideoxy-5-iodo-α-D-lyxofuranosyl sulfone

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Technology Process of phenyl 2-amino-N-benzyl-2N,3O-carbamoyl-2,5-dideoxy-5-iodo-α-D-lyxofuranosyl sulfone

There total 6 articles about phenyl 2-amino-N-benzyl-2N,3O-carbamoyl-2,5-dideoxy-5-iodo-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: 78.0%

: 220458-76-4
phenyl 2-amino-N-benzyl-2N,3O-carbamoyl-2-deoxy-α-D-lyxofuranosyl sulfone

: 220458-82-2
phenyl 2-amino-N-benzyl-2N,3O-carbamoyl-2,5-dideoxy-5-iodo-α-D-lyxofuranosyl sulfone

Guidance literature:: With iodine; triphenylphosphine; In pyridine; dichloromethane; toluene; at 80 ℃; for 4h;
DOI:10.3987/com-98-8292

Reference yield:

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

: 220458-82-2
phenyl 2-amino-N-benzyl-2N,3O-carbamoyl-2,5-dideoxy-5-iodo-α-D-lyxofuranosyl sulfone

Guidance literature:: Multi-step reaction with 6 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

4: H₅IO₆ / ethyl acetate / 3 h / Ambient temperature

5: 97 percent / NaBH₄ / aq. ethanol / 0 deg C, 15 min then r.t., 30 min

6: 78 percent / Ph₃P, iodine / toluene; CH₂Cl₂; pyridine / 4 h / 80 °C

With sodium tetrahydroborate; n-butyllithium; potassium tert-butylate; iodine; sodium hydrogencarbonate; periodic acid; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; In tetrahydrofuran; pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; ethanol; dichloromethane; ethyl acetate; toluene;
DOI:10.3987/com-98-8292

Reference yield:

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

: 220458-82-2
phenyl 2-amino-N-benzyl-2N,3O-carbamoyl-2,5-dideoxy-5-iodo-α-D-lyxofuranosyl sulfone

Guidance literature:: Multi-step reaction with 4 steps

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

2: H₅IO₆ / ethyl acetate / 3 h / Ambient temperature

3: 97 percent / NaBH₄ / aq. ethanol / 0 deg C, 15 min then r.t., 30 min

4: 78 percent / Ph₃P, iodine / toluene; CH₂Cl₂; pyridine / 4 h / 80 °C

With sodium tetrahydroborate; potassium tert-butylate; iodine; periodic acid; triphenylphosphine; In tetrahydrofuran; pyridine; ethanol; dichloromethane; ethyl acetate; toluene;
DOI:10.3987/com-98-8292