phenyl 2-benzylamino-2N,3O-carbamoyl-2,5-dideoxy-5-iodo-α-D-ribofuranosyl sulfone

Base Information

• Chemical Name: phenyl 2-benzylamino-2N,3O-carbamoyl-2,5-dideoxy-5-iodo-α-D-ribofuranosyl sulfone
• CAS No.: 219697-72-0
• Molecular Formula: C₁₉H₁₈INO₅S
• Molecular Weight: 499.326
• Mol file: 219697-72-0.mol

Synonyms:phenyl 2-benzylamino-2N,3O-carbamoyl-2,5-dideoxy-5-iodo-α-D-ribofuranosyl sulfone

Chemical Property of phenyl 2-benzylamino-2N,3O-carbamoyl-2,5-dideoxy-5-iodo-α-D-ribofuranosyl sulfone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of phenyl 2-benzylamino-2N,3O-carbamoyl-2,5-dideoxy-5-iodo-α-D-ribofuranosyl sulfone

There total 5 articles about phenyl 2-benzylamino-2N,3O-carbamoyl-2,5-dideoxy-5-iodo-α-D-ribofuranosyl 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: 95.0%

phenyl 2-benzylamino-2N,3O-carbamoyl-2-deoxy-α-D-ribofuranosyl sulfone (219697-71-9) → phenyl 2-benzylamino-2N,3O-carbamoyl-2,5-dideoxy-5-iodo-α-D-ribofuranosyl sulfone (219697-72-0)

Guidance literature:

With pyridine; iodine; triphenylphosphine; In dichloromethane; toluene; for 4h; Heating;

DOI:10.1139/v98-112

Reference yield:

benzyl isothiocyanate (3173-56-6) → phenyl 2-benzylamino-2N,3O-carbamoyl-2,5-dideoxy-5-iodo-α-D-ribofuranosyl sulfone (219697-72-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 89 percent / t-BuOK / tetrahydrofuran / a) 0 deg C, 1 h, b) RT, 20 h

2: 88 percent / Me₃SiCl, MeOH / 1 h / 0 °C

3: 95 percent / I₂, Ph₃P, pyridine / toluene; CH₂Cl₂ / 4 h / Heating

With pyridine; methanol; chloro-trimethyl-silane; potassium tert-butylate; iodine; triphenylphosphine; In tetrahydrofuran; dichloromethane; toluene;

DOI:10.1139/v98-112

Reference yield:

(2R,3S)-5-Benzenesulfonyl-2-(tert-butyl-dimethyl-silanyloxymethyl)-2,3-dihydro-furan-3-ol (219697-69-5) → phenyl 2-benzylamino-2N,3O-carbamoyl-2,5-dideoxy-5-iodo-α-D-ribofuranosyl sulfone (219697-72-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 89 percent / t-BuOK / tetrahydrofuran / a) 0 deg C, 1 h, b) RT, 20 h

2: 88 percent / Me₃SiCl, MeOH / 1 h / 0 °C

3: 95 percent / I₂, Ph₃P, pyridine / toluene; CH₂Cl₂ / 4 h / Heating

With pyridine; methanol; chloro-trimethyl-silane; potassium tert-butylate; iodine; triphenylphosphine; In tetrahydrofuran; dichloromethane; toluene;

DOI:10.1139/v98-112

upstream raw materials:

phenyl 2-benzylamino-2N,3O-carbamoyl-2-deoxy-α-D-ribofuranosyl sulfone

benzyl isothiocyanate

(2R,3S)-5-Benzenesulfonyl-2-(tert-butyl-dimethyl-silanyloxymethyl)-2,3-dihydro-furan-3-ol

Downstream raw materials:

(4S,5R)-3-benzyl-4-(benzyloxymethyl)-5-vinyl-2-oxazolidinone

(4S,5S)-3-benzyl-4-(benzyloxymethyl)-5-formyl-2-oxazolidinone

(4S,5R)-3-benzyl-4-(hydroxymethyl)-5-vinyl-2-oxazolidinone