(2R,3R,4S)-3-acetylamino-4-(tert-butoxycarbonylamino)-3,4-dihydro-2H-pyran-2,6-dicarboxylic acid 6-benzhydryl ester 2-(2,3,4,5,6-pentafluoro-phenyl) ester

Base Information

• Chemical Name: (2R,3R,4S)-3-acetylamino-4-(tert-butoxycarbonylamino)-3,4-dihydro-2H-pyran-2,6-dicarboxylic acid 6-benzhydryl ester 2-(2,3,4,5,6-pentafluoro-phenyl) ester
• CAS No.: 182251-52-1
• Molecular Formula: C₃₃H₂₉F₅N₂O₈
• Molecular Weight: 676.594
• Mol file: 182251-52-1.mol

Synonyms:(2R,3R,4S)-3-acetylamino-4-(tert-butoxycarbonylamino)-3,4-dihydro-2H-pyran-2,6-dicarboxylic acid 6-benzhydryl ester 2-(2,3,4,5,6-pentafluoro-phenyl) ester

Chemical Property of (2R,3R,4S)-3-acetylamino-4-(tert-butoxycarbonylamino)-3,4-dihydro-2H-pyran-2,6-dicarboxylic acid 6-benzhydryl ester 2-(2,3,4,5,6-pentafluoro-phenyl) ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R,4S)-3-acetylamino-4-(tert-butoxycarbonylamino)-3,4-dihydro-2H-pyran-2,6-dicarboxylic acid 6-benzhydryl ester 2-(2,3,4,5,6-pentafluoro-phenyl) ester

There total 7 articles about (2R,3R,4S)-3-acetylamino-4-(tert-butoxycarbonylamino)-3,4-dihydro-2H-pyran-2,6-dicarboxylic acid 6-benzhydryl ester 2-(2,3,4,5,6-pentafluoro-phenyl) ester 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: 100.0%

pentafluorophenyl trifloroacetate (14533-84-7) + (2R,3R,4S)-3-Acetylamino-4-(tert-butoxycarbonylamino)-3,4-dihydro-2H-pyran-2,6-dicarboxylic acid 6-benzhydryl ester (182251-51-0) → (2R,3R,4S)-3-acetylamino-4-(tert-butoxycarbonylamino)-3,4-dihydro-2H-pyran-2,6-dicarboxylic acid 6-benzhydryl ester 2-(2,3,4,5,6-pentafluoro-phenyl) ester (182251-52-1)

Guidance literature:

With pyridine; In N,N-dimethyl-formamide;

DOI:10.1016/0960-894X(96)00318-6

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → (2R,3R,4S)-3-acetylamino-4-(tert-butoxycarbonylamino)-3,4-dihydro-2H-pyran-2,6-dicarboxylic acid 6-benzhydryl ester 2-(2,3,4,5,6-pentafluoro-phenyl) ester (182251-52-1)

Guidance literature:

Multi-step reaction with 5 steps

1: aq. NaHCO₃ / dioxane / 18 h / 23 °C

2: aq. HCl / CH₂Cl₂ / 24 h / 23 °C

3: aq. NaIO₄ / methanol / 3 h / 23 °C

4: NaClO₂, aq. KH₂PO₄, cyclohexene / 2-methyl-propan-2-ol / 18 h / 23 °C

5: 97 percent / pyridine / dimethylformamide / 3 h / 23 °C

With pyridine; hydrogenchloride; sodium chlorite; sodium periodate; potassium dihydrogenphosphate; sodium hydrogencarbonate; cyclohexene; In 1,4-dioxane; methanol; dichloromethane; N,N-dimethyl-formamide; tert-butyl alcohol;

Reference yield:

(4S,5R,6R)-5-Acetylamino-4-tert-butoxycarbonylamino-6-((1R,2R)-1,2,3-trihydroxy-propyl)-5,6-dihydro-4H-pyran-2-carboxylic acid (166830-74-6) → (2R,3R,4S)-3-acetylamino-4-(tert-butoxycarbonylamino)-3,4-dihydro-2H-pyran-2,6-dicarboxylic acid 6-benzhydryl ester 2-(2,3,4,5,6-pentafluoro-phenyl) ester (182251-52-1)

Guidance literature:

Multi-step reaction with 4 steps

1: aq. HCl / CH₂Cl₂ / 24 h / 23 °C

2: aq. NaIO₄ / methanol / 3 h / 23 °C

3: NaClO₂, aq. KH₂PO₄, cyclohexene / 2-methyl-propan-2-ol / 18 h / 23 °C

4: 97 percent / pyridine / dimethylformamide / 3 h / 23 °C

With pyridine; hydrogenchloride; sodium chlorite; sodium periodate; potassium dihydrogenphosphate; cyclohexene; In methanol; dichloromethane; N,N-dimethyl-formamide; tert-butyl alcohol;

upstream raw materials:

pentafluorophenyl trifloroacetate

(2R,3R,4S)-3-Acetylamino-4-(tert-butoxycarbonylamino)-3,4-dihydro-2H-pyran-2,6-dicarboxylic acid 6-benzhydryl ester

di-tert-butyl dicarbonate

5-acetamido-4-amino-2,6-anhydro-3,4,5-trideoxy-D-glycero-D-galacto-non-2-enonic acid

Downstream raw materials:

(4S,5R,6R)-5-Acetylamino-4-tert-butoxycarbonylamino-6-propylcarbamoyl-5,6-dihydro-4H-pyran-2-carboxylic acid benzhydryl ester

(4S,5R,6R)-5-Acetylamino-4-(tert-butoxycarbonylamino)-6-(methylpropylcarbamoyl)-5,6-dihydro-4H-pyran-2-carboxylic acid benzhydryl ester

(4S,5R,6R)-5-Acetylamino-4-tert-butoxycarbonylamino-6-dipropylcarbamoyl-5,6-dihydro-4H-pyran-2-carboxylic acid benzhydryl ester

(4S,5R,6R)-5-Acetylamino-4-tert-butoxycarbonylamino-6-(pyrrolidine-1-carbonyl)-5,6-dihydro-4H-pyran-2-carboxylic acid benzhydryl ester