DL-penta-O-acetyl-(1,3,5/2,4)-6-methylene-1,2,3,4,5-cyclohexanepentol

Base Information

• Chemical Name: DL-penta-O-acetyl-(1,3,5/2,4)-6-methylene-1,2,3,4,5-cyclohexanepentol
• CAS No.: 86195-43-9
• Molecular Formula: C₁₇H₂₂O₁₀
• Molecular Weight: 386.356
• Mol file: 86195-43-9.mol

Synonyms:DL-penta-O-acetyl-(1,3,5/2,4)-6-methylene-1,2,3,4,5-cyclohexanepentol

Chemical Property of DL-penta-O-acetyl-(1,3,5/2,4)-6-methylene-1,2,3,4,5-cyclohexanepentol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of DL-penta-O-acetyl-(1,3,5/2,4)-6-methylene-1,2,3,4,5-cyclohexanepentol

There total 4 articles about DL-penta-O-acetyl-(1,3,5/2,4)-6-methylene-1,2,3,4,5-cyclohexanepentol 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: 73.0%

acetic anhydride (108-24-7) + DL-tri-O-acetyl-(1,3/2,6)-6-bromo-4-bromomethyl-4-cyclohexene-1,2,3-triol (74615-52-4,74645-46-8,87726-28-1,87726-29-2) → DL-penta-O-acetyl-(1,3,5/2,4)-6-methylene-1,2,3,4,5-cyclohexanepentol (86195-43-9) + (1SR,2RS,3RS,4SR)-5-[(acetyloxy)methyl]cyclohex-5-ene-1,2,3,4-tetrayl tetraacetate (74615-58-0,74645-47-9,87726-31-6,87726-34-9,111002-24-5)

Guidance literature:

With silver(I) acetate; acetic acid; at 80 ℃; for 3h;

DOI:10.1246/bcsj.56.505

Reference yield:

DL-(1,3/2)-1,2,3-tri-O-acetyl-4-methylene-5-cyclohexene-1,2,3-triol (74024-01-4) → DL-penta-O-acetyl-(1,3,5/2,4)-6-methylene-1,2,3,4,5-cyclohexanepentol (86195-43-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 45 percent / Br₂ / acetic acid; acetic anhydride / 0.83 h

2: 12 percent / silver acetate, acetic acid / 3 h / 80 °C

With bromine; silver(I) acetate; acetic acid; In acetic anhydride; acetic acid;

DOI:10.1246/bcsj.56.505

Reference yield:

→ DL-penta-O-acetyl-(1,3,5/2,4)-6-methylene-1,2,3,4,5-cyclohexanepentol (86195-43-9)

Guidance literature:

With chloroform; hydrogen iodide;

DOI:10.1002/hlca.19530360620

upstream raw materials:

acetic anhydride

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

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

Downstream raw materials:

6ξ-methyl-cyclohexane-1r,2t,3c,4t,5c-pentaol

6-methylene-cyclohexane-1r,2t,3c,4t,5c-pentaol