Acetic acid (1R,2S,5S,6R)-5,6-diacetoxy-4-acetoxymethyl-2-((3aR,4R,5aS,9aS,9bR)-2,2,8,8-tetramethyl-hexahydro-[1,3]dioxolo[4',5':3,4]benzo[1,2-d][1,3]dioxin-4-ylamino)-cyclohex-3-enyl ester

Base Information

• Chemical Name: Acetic acid (1R,2S,5S,6R)-5,6-diacetoxy-4-acetoxymethyl-2-((3aR,4R,5aS,9aS,9bR)-2,2,8,8-tetramethyl-hexahydro-[1,3]dioxolo[4',5':3,4]benzo[1,2-d][1,3]dioxin-4-ylamino)-cyclohex-3-enyl ester
• CAS No.: 79527-23-4
• Molecular Formula: C₂₈H₄₁NO₁₂
• Molecular Weight: 583.633

Synonyms:

Chemical Property of Acetic acid (1R,2S,5S,6R)-5,6-diacetoxy-4-acetoxymethyl-2-((3aR,4R,5aS,9aS,9bR)-2,2,8,8-tetramethyl-hexahydro-[1,3]dioxolo[4',5':3,4]benzo[1,2-d][1,3]dioxin-4-ylamino)-cyclohex-3-enyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of Acetic acid (1R,2S,5S,6R)-5,6-diacetoxy-4-acetoxymethyl-2-((3aR,4R,5aS,9aS,9bR)-2,2,8,8-tetramethyl-hexahydro-[1,3]dioxolo[4',5':3,4]benzo[1,2-d][1,3]dioxin-4-ylamino)-cyclohex-3-enyl ester

There total 8 articles about Acetic acid (1R,2S,5S,6R)-5,6-diacetoxy-4-acetoxymethyl-2-((3aR,4R,5aS,9aS,9bR)-2,2,8,8-tetramethyl-hexahydro-[1,3]dioxolo[4',5':3,4]benzo[1,2-d][1,3]dioxin-4-ylamino)-cyclohex-3-enyl 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:

DL-1,2,3-tri-O-acetyl-(1,3/2,4,6)-6-acetoxymethyl-4-bromo-1,2,3-cyclohexanetriol (70878-41-0) → Acetic acid (1S,2R,5R,6S)-5,6-diacetoxy-4-acetoxymethyl-2-((3aR,4R,5aS,9aS,9bR)-2,2,8,8-tetramethyl-hexahydro-[1,3]dioxolo[4',5':3,4]benzo[1,2-d][1,3]dioxin-4-ylamino)-cyclohex-3-enyl ester (79527-23-4,79549-80-7)

Guidance literature:

Multi-step reaction with 5 steps

1: 90 percent / HCl / ethanol / 3 h / 80 °C

2: 86 percent / TsOH / dimethylformamide / 3 h / 60 °C

3: 78 percent / NaN₃ / dimethylsulfoxide / 15 h / 110 °C

4: 76 percent / H₂ / Ra-Ni / ethanol

5: disopropylethylamine / dimethylformamide / 480 h / Ambient temperature

With hydrogenchloride; sodium azide; hydrogen; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; Ra-Ni; In ethanol; dimethyl sulfoxide; N,N-dimethyl-formamide;

DOI:10.1246/cl.1981.947

Reference yield:

DL-(1,3/2,4,6)-4-bromo-6-hydroxymethyl-1,2,3-cyclohexanetriol (79527-13-2) → Acetic acid (1S,2R,5R,6S)-5,6-diacetoxy-4-acetoxymethyl-2-((3aR,4R,5aS,9aS,9bR)-2,2,8,8-tetramethyl-hexahydro-[1,3]dioxolo[4',5':3,4]benzo[1,2-d][1,3]dioxin-4-ylamino)-cyclohex-3-enyl ester (79527-23-4,79549-80-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 86 percent / TsOH / dimethylformamide / 3 h / 60 °C

2: 78 percent / NaN₃ / dimethylsulfoxide / 15 h / 110 °C

3: 76 percent / H₂ / Ra-Ni / ethanol

4: disopropylethylamine / dimethylformamide / 480 h / Ambient temperature

With sodium azide; hydrogen; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; Ra-Ni; In ethanol; dimethyl sulfoxide; N,N-dimethyl-formamide;

DOI:10.1246/cl.1981.947

Reference yield:

DL-1,7:2,3-di-O-isopropylidene-(1,3,4/2,6)-4-azido-6-hydroxymethyl-1,2,3-cyclohexanetriol → Acetic acid (1S,2R,5R,6S)-5,6-diacetoxy-4-acetoxymethyl-2-((3aR,4R,5aS,9aS,9bR)-2,2,8,8-tetramethyl-hexahydro-[1,3]dioxolo[4',5':3,4]benzo[1,2-d][1,3]dioxin-4-ylamino)-cyclohex-3-enyl ester (79527-23-4,79549-80-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 76 percent / H₂ / Ra-Ni / ethanol

2: disopropylethylamine / dimethylformamide / 480 h / Ambient temperature

With hydrogen; N-ethyl-N,N-diisopropylamine; Ra-Ni; In ethanol; N,N-dimethyl-formamide;

DOI:10.1246/cl.1981.947

upstream raw materials:

DL-2,3:4,7-di-O-isopropylidene-(1,2,4/3,5)-2,3,4-trihydroxy-5-(hydroxymethyl)cyclohexylamine

DL-1,2,3-tri-O-acetyl-(1,3,6/2)-4-acetoxymethyl-6-bromo-4-cyclohexene-1,2,3-triol

DL-1,2,3-tri-O-acetyl-(1,3/2,4,6)-6-acetoxymethyl-4-bromo-1,2,3-cyclohexanetriol

DL-(1,3/2,4,6)-4-bromo-6-hydroxymethyl-1,2,3-cyclohexanetriol

Downstream raw materials:

Acetic acid (1R,2R,3S,4S,6R)-2,3-diacetoxy-4-acetoxymethyl-6-((1R,4R,5S,6S)-4,5,6-triacetoxy-3-acetoxymethyl-cyclohex-2-enylamino)-cyclohexyl ester

(1R,2R,3S,6S)-4-Hydroxymethyl-6-((1S,2S,3S,4R,5R)-2,3,4-trihydroxy-5-hydroxymethyl-cyclohexylamino)-cyclohex-4-ene-1,2,3-triol

(1S,2S,3R,6R)-4-Hydroxymethyl-6-((1S,2S,3S,4R,5R)-2,3,4-trihydroxy-5-hydroxymethyl-cyclohexylamino)-cyclohex-4-ene-1,2,3-triol

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