Acetic acid (2S,4S,5S)-5-acetylamino-2-methylcarbamoyl-2-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-4-yl ester

Base Information

• Chemical Name: Acetic acid (2S,4S,5S)-5-acetylamino-2-methylcarbamoyl-2-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-4-yl ester
• CAS No.: 146820-99-7
• Molecular Formula: C₃₉H₄₈N₂O₁₁
• Molecular Weight: 720.817
• Mol file: 146820-99-7.mol

Synonyms:

Chemical Property of Acetic acid (2S,4S,5S)-5-acetylamino-2-methylcarbamoyl-2-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-4-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acetic acid (2S,4S,5S)-5-acetylamino-2-methylcarbamoyl-2-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-4-yl ester

There total 13 articles about Acetic acid (2S,4S,5S)-5-acetylamino-2-methylcarbamoyl-2-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-4-yl 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:

methyl-2,3,4-tri-O-benzyl-6-O-trifluoromethanesulfonyl-α-D-glucopyranoside (76679-47-5) → Acetic acid (2S,4S,5S)-5-acetylamino-2-methylcarbamoyl-2-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-4-yl ester (146820-99-7)

Guidance literature:

Multi-step reaction with 11 steps

1: 1) NaH / 1) THF, -10 deg C, 2) r.t.

2: 81 percent / Dowex 50 WX₂ / methanol / 0 °C

3: 91 percent / imidazole / dimethylformamide

4: 1) Tf₂O, pyridine, 2) NaN₃ / 1) -30 deg C

5: 73 percent / aq. TFA / CH₂Cl₂

6: pyridine

7: 95 percent / DBU / CH₂Cl₂ / -78 °C

8: ethanol / 0 °C

9: 1) N-iodosuccinimide (NIS), 2) pyridine / 1) EtCN, -78 deg C

10: Bu₃SnH, AIBN / toluene / 0.5 h / 90 °C

With pyridine; 1H-imidazole; N-iodo-succinimide; sodium azide; 2,2'-azobis(isobutyronitrile); trifluoromethylsulfonic anhydride; Dowex 50 WX₂; tri-n-butyl-tin hydride; sodium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; trifluoroacetic acid; In methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1016/S0040-4039(00)60807-9

Reference yield:

methyl 3,4:5,6-di-O-isopropylidene-D-gluconate (114743-85-0) → Acetic acid (2S,4S,5S)-5-acetylamino-2-methylcarbamoyl-2-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-4-yl ester (146820-99-7)

Guidance literature:

Multi-step reaction with 11 steps

1: 1) NaH / 1) THF, -10 deg C, 2) r.t.

2: 81 percent / Dowex 50 WX₂ / methanol / 0 °C

3: 91 percent / imidazole / dimethylformamide

4: 1) Tf₂O, pyridine, 2) NaN₃ / 1) -30 deg C

5: 73 percent / aq. TFA / CH₂Cl₂

6: pyridine

7: 95 percent / DBU / CH₂Cl₂ / -78 °C

8: ethanol / 0 °C

9: 1) N-iodosuccinimide (NIS), 2) pyridine / 1) EtCN, -78 deg C

10: Bu₃SnH, AIBN / toluene / 0.5 h / 90 °C

With pyridine; 1H-imidazole; N-iodo-succinimide; sodium azide; 2,2'-azobis(isobutyronitrile); trifluoromethylsulfonic anhydride; Dowex 50 WX₂; tri-n-butyl-tin hydride; sodium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; trifluoroacetic acid; In methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1016/S0040-4039(00)60807-9

Reference yield:

(R)-[(4S,5R)-5-((R)-1,2-Dihydroxy-ethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-acetic acid methyl ester → Acetic acid (2S,4S,5S)-5-acetylamino-2-methylcarbamoyl-2-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-4-yl ester (146820-99-7)

Guidance literature:

Multi-step reaction with 9 steps

1: 91 percent / imidazole / dimethylformamide

2: 1) Tf₂O, pyridine, 2) NaN₃ / 1) -30 deg C

3: 73 percent / aq. TFA / CH₂Cl₂

4: pyridine

5: 95 percent / DBU / CH₂Cl₂ / -78 °C

6: ethanol / 0 °C

7: 1) N-iodosuccinimide (NIS), 2) pyridine / 1) EtCN, -78 deg C

8: Bu₃SnH, AIBN / toluene / 0.5 h / 90 °C

With pyridine; 1H-imidazole; N-iodo-succinimide; sodium azide; 2,2'-azobis(isobutyronitrile); trifluoromethylsulfonic anhydride; tri-n-butyl-tin hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; trifluoroacetic acid; In ethanol; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1016/S0040-4039(00)60807-9

upstream raw materials:

acetic anhydride

methyl-2,3,4-tri-O-benzyl-6-O-trifluoromethanesulfonyl-α-D-glucopyranoside

methyl 3,4:5,6-di-O-isopropylidene-D-gluconate

(R)-((4R,5S,4'R)-2,2,2',2'-Tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-acetic acid methyl ester