{(S)-1-[(3R,4R,6S)-4-Benzyloxy-6-(benzyloxycarbonylamino-methyl)-2-oxo-tetrahydro-pyran-3-ylcarbamoyl]-2-methyl-propyl}-carbamic acid benzyl ester

Base Information

• Chemical Name: {(S)-1-[(3R,4R,6S)-4-Benzyloxy-6-(benzyloxycarbonylamino-methyl)-2-oxo-tetrahydro-pyran-3-ylcarbamoyl]-2-methyl-propyl}-carbamic acid benzyl ester
• CAS No.: 159489-48-2
• Molecular Formula: C₃₄H₃₉N₃O₈
• Molecular Weight: 617.699

Synonyms:

Chemical Property of {(S)-1-[(3R,4R,6S)-4-Benzyloxy-6-(benzyloxycarbonylamino-methyl)-2-oxo-tetrahydro-pyran-3-ylcarbamoyl]-2-methyl-propyl}-carbamic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of {(S)-1-[(3R,4R,6S)-4-Benzyloxy-6-(benzyloxycarbonylamino-methyl)-2-oxo-tetrahydro-pyran-3-ylcarbamoyl]-2-methyl-propyl}-carbamic acid benzyl ester

There total 11 articles about {(S)-1-[(3R,4R,6S)-4-Benzyloxy-6-(benzyloxycarbonylamino-methyl)-2-oxo-tetrahydro-pyran-3-ylcarbamoyl]-2-methyl-propyl}-carbamic acid benzyl 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:

Toluene-4-sulfonic acid (2R,3R,4R,5R,6S)-2-azidomethyl-5-benzyloxycarbonylamino-3-hydroxy-6-methoxy-tetrahydro-pyran-4-yl ester (60076-43-9) → {(S)-1-[(3R,4R,6S)-4-Benzyloxy-6-(benzyloxycarbonylamino-methyl)-2-oxo-tetrahydro-pyran-3-ylcarbamoyl]-2-methyl-propyl}-carbamic acid benzyl ester (159489-48-2)

Guidance literature:

Multi-step reaction with 10 steps

1: LiALH₄ / tetrahydrofuran / -20 - -15 °C

2: 67 percent / Na₂CO₃

3: K₂CO₃ / methanol

4: 60 percent / LiAlH₄ / tetrahydrofuran / -5 °C

5: H₂ / Pd/C / methanol

6: 61 percent / DCC, HOBt / tetrahydrofuran

7: TFA / CH₂Cl₂ / 0 °C

8: 61 percent / NaHCO₃

9: 61 percent / BaO, Ba(OH)2 / dimethylformamide

10: 1.) TsOH, 2.) PDC / 1.) dioxane, 80 deg C, 2.) DMF

With barium dihydroxide; lithium aluminium tetrahydride; dipyridinium dichromate; hydrogen; sodium hydrogencarbonate; sodium carbonate; potassium carbonate; benzotriazol-1-ol; toluene-4-sulfonic acid; dicyclohexyl-carbodiimide; trifluoroacetic acid; barium(II) oxide; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)60720-7

Reference yield:

[(2S,3R,4R,6S)-6-(tert-Butoxycarbonylamino-methyl)-4-hydroxy-2-methoxy-tetrahydro-pyran-3-yl]-carbamic acid benzyl ester (159489-35-7) → {(S)-1-[(3R,4R,6S)-4-Benzyloxy-6-(benzyloxycarbonylamino-methyl)-2-oxo-tetrahydro-pyran-3-ylcarbamoyl]-2-methyl-propyl}-carbamic acid benzyl ester (159489-48-2)

Guidance literature:

Multi-step reaction with 6 steps

1: H₂ / Pd/C / methanol

2: 61 percent / DCC, HOBt / tetrahydrofuran

3: TFA / CH₂Cl₂ / 0 °C

4: 61 percent / NaHCO₃

5: 61 percent / BaO, Ba(OH)2 / dimethylformamide

6: 1.) TsOH, 2.) PDC / 1.) dioxane, 80 deg C, 2.) DMF

With barium dihydroxide; dipyridinium dichromate; hydrogen; sodium hydrogencarbonate; benzotriazol-1-ol; toluene-4-sulfonic acid; dicyclohexyl-carbodiimide; trifluoroacetic acid; barium(II) oxide; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)60720-7

Reference yield:

[(1R,2R,4S,5R,6S)-2-(tert-Butoxycarbonylamino-methyl)-4-methoxy-3,7-dioxa-bicyclo[4.1.0]hept-5-yl]-carbamic acid benzyl ester → {(S)-1-[(3R,4R,6S)-4-Benzyloxy-6-(benzyloxycarbonylamino-methyl)-2-oxo-tetrahydro-pyran-3-ylcarbamoyl]-2-methyl-propyl}-carbamic acid benzyl ester (159489-48-2)

Guidance literature:

Multi-step reaction with 7 steps

1: 60 percent / LiAlH₄ / tetrahydrofuran / -5 °C

2: H₂ / Pd/C / methanol

3: 61 percent / DCC, HOBt / tetrahydrofuran

4: TFA / CH₂Cl₂ / 0 °C

5: 61 percent / NaHCO₃

6: 61 percent / BaO, Ba(OH)2 / dimethylformamide

7: 1.) TsOH, 2.) PDC / 1.) dioxane, 80 deg C, 2.) DMF

With barium dihydroxide; lithium aluminium tetrahydride; dipyridinium dichromate; hydrogen; sodium hydrogencarbonate; benzotriazol-1-ol; toluene-4-sulfonic acid; dicyclohexyl-carbodiimide; trifluoroacetic acid; barium(II) oxide; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)60720-7

upstream raw materials:

{(S)-1-[(2S,3R,4R,6S)-4-Benzyloxy-6-(benzyloxycarbonylamino-methyl)-2-methoxy-tetrahydro-pyran-3-ylcarbamoyl]-2-methyl-propyl}-carbamic acid benzyl ester

Toluene-4-sulfonic acid (2R,3R,4R,5R,6S)-2-azidomethyl-5-benzyloxycarbonylamino-3-hydroxy-6-methoxy-tetrahydro-pyran-4-yl ester

(S)-N-(benzyloxycarbonyl)valine

[(2S,3R,4R,6S)-6-(tert-Butoxycarbonylamino-methyl)-4-hydroxy-2-methoxy-tetrahydro-pyran-3-yl]-carbamic acid benzyl ester

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