DL-(1,3/2)-1,2,3-tri-O-acetyl-4-methylene-5-cyclohexene-1,2,3-triol

Base Information

• Chemical Name: DL-(1,3/2)-1,2,3-tri-O-acetyl-4-methylene-5-cyclohexene-1,2,3-triol
• CAS No.: 74024-01-4
• Molecular Formula: C₁₃H₁₆O₆
• Molecular Weight: 268.266
• Mol file: 74024-01-4.mol

Synonyms:DL-(1,3/2)-1,2,3-tri-O-acetyl-4-methylene-5-cyclohexene-1,2,3-triol

Chemical Property of DL-(1,3/2)-1,2,3-tri-O-acetyl-4-methylene-5-cyclohexene-1,2,3-triol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of DL-(1,3/2)-1,2,3-tri-O-acetyl-4-methylene-5-cyclohexene-1,2,3-triol

There total 4 articles about DL-(1,3/2)-1,2,3-tri-O-acetyl-4-methylene-5-cyclohexene-1,2,3-triol 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: 51.0%

DL-1,2,3-tri-O-acetyl-(1,3/2,4)-4-bromo-6-methylene-1,2,3-cyclohexenetriol (74023-99-7) → DL-(1,3/2)-1,2,3-tri-O-acetyl-4-methylene-5-cyclohexene-1,2,3-triol (74024-01-4)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In toluene; for 6h; Heating;

DOI:10.1246/bcsj.53.455

Reference yield: 45.0%

DL-(1,3/2,4,6)-1,2,3-tri-O-acetyl-4-bromo-6-bromomethyl-1,2,3-cyclohexanetriol (70838-35-6) → DL-(1,3/2)-1,2,3-tri-O-acetyl-4-methylene-5-cyclohexene-1,2,3-triol (74024-01-4)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In toluene; for 0.5h; Heating;

DOI:10.1246/bcsj.53.455

Reference yield: 5.0%

sodium benzoate (532-32-1) + DL-(1,3/2,4,6)-1,2,3-tri-O-acetyl-4-bromo-6-bromomethyl-1,2,3-cyclohexanetriol (70838-35-6) → DL-(1,3/2)-1,2,3-tri-O-acetyl-4-methylene-5-cyclohexene-1,2,3-triol (74024-01-4) + DL-O-triacetyl-(1,3/2,4)-4-<(benzoyloxy)methyl>-5-cyclohexene-1,2,3-triol (77144-65-1) + C27H28O10 (77144-66-2)

Guidance literature:

With lithium bromide; In N,N-dimethyl-formamide; at 100 ℃; for 20h;

DOI:10.1246/cl.1980.1559

upstream raw materials:

sodium benzoate

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

acetic anhydride

DL-1,2,3-tri-O-acetyl-(1,3/2,4)-4-bromo-6-methylene-1,2,3-cyclohexenetriol

Downstream raw materials:

Acetic acid (4aS,5R,6S,7S,8S,8aR)-8-acetoxy-5-hydroxy-2-phenyl-6-((3aR,4R,9aS,9bR)-2,2,8,8-tetramethyl-4,6,9a,9b-tetrahydro-3aH-[1,3]dioxolo[4',5':3,4]benzo[1,2-d][1,3]dioxin-4-ylamino)-hexahydro-benzo[1,3]dioxin-7-yl ester

Acetic acid (4aR,5S,6R,7S,8S,8aR)-8-acetoxy-6-hydroxy-2-phenyl-5-((3aR,4R,9aS,9bR)-2,2,8,8-tetramethyl-4,6,9a,9b-tetrahydro-3aH-[1,3]dioxolo[4',5':3,4]benzo[1,2-d][1,3]dioxin-4-ylamino)-hexahydro-benzo[1,3]dioxin-7-yl ester

DL-N-<(1SR)-4,7:5,6-di-O-isopropylidene-4,5,6-trihydroxy-3-(hydroxymethyl)-2-cyclohexenyl>-(1SR)-2,3-di-O-acetyl-4,7-O-benzylidene-(1,2,4/3,5,6)-2,3,4,6-tetrahydroxy-5-(hydroxymethyl)cyclohexylamine

N-<(1SR)-4,7:5,6-di-O-isopropylidene-4,5,6-trihydroxy-3-(hydroxymethyl)-2-cyclohexenyl>-(1SR)-3,4-di-O-acetyl-5,7-O-benzylidene-(1,3,5/2,4,6)-2,3,4,5-tetrahydroxy-6-(hydroxymethyl)cyclohexylamine