Acetic acid (2S,3S,4S,5R,6R)-2-acetoxymethyl-5-acetylamino-6-methoxy-3-((1R,2S,3S,4S,5R)-2,3,4-triacetoxy-5-acetoxymethyl-cyclohexylamino)-tetrahydro-pyran-4-yl ester

Base Information

• Chemical Name: Acetic acid (2S,3S,4S,5R,6R)-2-acetoxymethyl-5-acetylamino-6-methoxy-3-((1R,2S,3S,4S,5R)-2,3,4-triacetoxy-5-acetoxymethyl-cyclohexylamino)-tetrahydro-pyran-4-yl ester
• CAS No.: 208524-50-9
• Molecular Formula: C₂₈H₄₂N₂O₁₅
• Molecular Weight: 646.646

Synonyms:

Chemical Property of Acetic acid (2S,3S,4S,5R,6R)-2-acetoxymethyl-5-acetylamino-6-methoxy-3-((1R,2S,3S,4S,5R)-2,3,4-triacetoxy-5-acetoxymethyl-cyclohexylamino)-tetrahydro-pyran-4-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acetic acid (2S,3S,4S,5R,6R)-2-acetoxymethyl-5-acetylamino-6-methoxy-3-((1R,2S,3S,4S,5R)-2,3,4-triacetoxy-5-acetoxymethyl-cyclohexylamino)-tetrahydro-pyran-4-yl ester

There total 10 articles about Acetic acid (2S,3S,4S,5R,6R)-2-acetoxymethyl-5-acetylamino-6-methoxy-3-((1R,2S,3S,4S,5R)-2,3,4-triacetoxy-5-acetoxymethyl-cyclohexylamino)-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-acetamido-3,6-di-O-benzyl-β-D-glucopyranoside (144685-11-0) → Acetic acid (2S,3S,4S,5R,6R)-2-acetoxymethyl-5-acetylamino-6-methoxy-3-((1R,2S,3S,4S,5R)-2,3,4-triacetoxy-5-acetoxymethyl-cyclohexylamino)-tetrahydro-pyran-4-yl ester (208524-50-9)

Guidance literature:

Multi-step reaction with 9 steps

1: Ac₂O, DMSO / 20 h / Ambient temperature

2: 49 percent / L-selectride / tetrahydrofuran / 7 h / refrigeration

3: pyridine / 0.5 h / Ambient temperature

4: NaN₃ / dimethylformamide; H₂O / 32 h / 100 °C

5: 81 percent / hydrogen / 10percent Pd/C / ethanol / 8.5 h / Ambient temperature

6: 2) pyridine / 1) isopropanol, 120 deg C, 15 d

7: 80percent aq. AcOH / 0.5 h / 80 °C

8: hydrogen, HCl / 10percent Pd/C / methanol / 0.5 h / Ambient temperature

9: pyridine

With pyridine; hydrogenchloride; sodium azide; hydrogen; acetic anhydride; L-Selectride; acetic acid; dimethyl sulfoxide; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; water; N,N-dimethyl-formamide;

DOI:10.1002/(SICI)1099-0690(199806)1998:6<1099::AID-EJOC1099<3.0.CO;2-R

Reference yield:

methyl 2-acetamido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside (142560-73-4) → Acetic acid (2S,3S,4S,5R,6R)-2-acetoxymethyl-5-acetylamino-6-methoxy-3-((1R,2S,3S,4S,5R)-2,3,4-triacetoxy-5-acetoxymethyl-cyclohexylamino)-tetrahydro-pyran-4-yl ester (208524-50-9)

Guidance literature:

Multi-step reaction with 10 steps

1: 74 percent / NaCNBH₃ / tetrahydrofuran / 1 h / Ambient temperature

2: Ac₂O, DMSO / 20 h / Ambient temperature

3: 49 percent / L-selectride / tetrahydrofuran / 7 h / refrigeration

4: pyridine / 0.5 h / Ambient temperature

5: NaN₃ / dimethylformamide; H₂O / 32 h / 100 °C

6: 81 percent / hydrogen / 10percent Pd/C / ethanol / 8.5 h / Ambient temperature

7: 2) pyridine / 1) isopropanol, 120 deg C, 15 d

8: 80percent aq. AcOH / 0.5 h / 80 °C

9: hydrogen, HCl / 10percent Pd/C / methanol / 0.5 h / Ambient temperature

10: pyridine

With pyridine; hydrogenchloride; sodium azide; hydrogen; acetic anhydride; L-Selectride; sodium cyanoborohydride; acetic acid; dimethyl sulfoxide; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; water; N,N-dimethyl-formamide;

DOI:10.1002/(SICI)1099-0690(199806)1998:6<1099::AID-EJOC1099<3.0.CO;2-R

Reference yield:

N-((2R,3R,4S,5S,6S)-5-Amino-4-hydroxy-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-3-yl)-acetamide (208524-38-3) → Acetic acid (2S,3S,4S,5R,6R)-2-acetoxymethyl-5-acetylamino-6-methoxy-3-((1R,2S,3S,4S,5R)-2,3,4-triacetoxy-5-acetoxymethyl-cyclohexylamino)-tetrahydro-pyran-4-yl ester (208524-50-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 2) pyridine / 1) isopropanol, 120 deg C, 15 d

2: 80percent aq. AcOH / 0.5 h / 80 °C

3: hydrogen, HCl / 10percent Pd/C / methanol / 0.5 h / Ambient temperature

4: pyridine

With pyridine; hydrogenchloride; hydrogen; acetic acid; palladium on activated charcoal; In methanol;

DOI:10.1002/(SICI)1099-0690(199806)1998:6<1099::AID-EJOC1099<3.0.CO;2-R

upstream raw materials:

acetic anhydride

methyl 2-acetamido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside

methyl 2-acetamido-3,6-di-O-benzyl-β-D-glucopyranoside

N-((2R,3R,4S,5S,6S)-5-Amino-4-hydroxy-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-3-yl)-acetamide

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