DL-1,2-di-O-acetyl-(1,3/2)-3-benzoyloxymethyl-5-cyclohexene-1,2-diol

Base Information

• Chemical Name: DL-1,2-di-O-acetyl-(1,3/2)-3-benzoyloxymethyl-5-cyclohexene-1,2-diol
• CAS No.: 74766-79-3
• Molecular Formula: C₁₈H₂₀O₆
• Molecular Weight: 332.353
• Mol file: 74766-79-3.mol

Synonyms:DL-1,2-di-O-acetyl-(1,3/2)-3-benzoyloxymethyl-5-cyclohexene-1,2-diol

Chemical Property of DL-1,2-di-O-acetyl-(1,3/2)-3-benzoyloxymethyl-5-cyclohexene-1,2-diol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of DL-1,2-di-O-acetyl-(1,3/2)-3-benzoyloxymethyl-5-cyclohexene-1,2-diol

There total 7 articles about DL-1,2-di-O-acetyl-(1,3/2)-3-benzoyloxymethyl-5-cyclohexene-1,2-diol 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: 26.0%

sodium benzoate (532-32-1) + DL-1,2-di-O-acetyl-(1,3,5/2)-5-bromo-3-bromomethyl-1,2-cyclohexanediol → DL-1,2-di-O-acetyl-(1,3/2)-3-benzoyloxymethyl-5-cyclohexene-1,2-diol (74766-79-3) + trans-4,5-diacetoxy-3-methylene-1-cyclohexene + DL-1,2-di-O-acetyl-(1,3/2)-3-benzoyloxymethyl-4-cyclohexene-1,2-diol + DL-1,2-di-O-acetyl-5-O-benzoyl-(1,3,5/2)-3-benzoyloxymethyl-1,2,5-cyclohexanetriol

Guidance literature:

With lithium bromide; In N,N-dimethyl-formamide; at 120 - 130 ℃; for 1h;

DOI:10.1246/bcsj.56.2319

Reference yield: 25.0%

DL-1,2-di-O-acetyl-(1,3,5/2)-3-benzoyloxymethyl-5-bromo-1,2-cyclohexanediol → DL-1,2-di-O-acetyl-(1,3/2)-3-benzoyloxymethyl-5-cyclohexene-1,2-diol (74766-79-3) + DL-1,2-di-O-acetyl-(1,3/2)-3-benzoyloxymethyl-4-cyclohexene-1,2-diol

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In toluene; for 14h; Heating;

DOI:10.1246/bcsj.56.2319

Reference yield: 8.0%

DL-1,2-di-O-acetyl-(1,3,5/2)-5-bromo-3-bromomethyl-1,2-cyclohexanediol → DL-1,2-di-O-acetyl-(1,3/2)-3-benzoyloxymethyl-5-cyclohexene-1,2-diol (74766-79-3) + trans-4,5-diacetoxy-3-methylene-1-cyclohexene + DL-1,2-di-O-acetyl-(1,3/2)-3-benzoyloxymethyl-4-cyclohexene-1,2-diol + DL-1,2-di-O-acetyl-5-O-benzoyl-(1,3,5/2)-3-benzoyloxymethyl-1,2,5-cyclohexanetriol

Guidance literature:

With sodium benzoate; lithium bromide; In N,N-dimethyl-formamide; at 120 - 130 ℃; for 1h;

DOI:10.1246/bcsj.56.2319

upstream raw materials:

sodium benzoate

acetic anhydride

3,4-di-O-acetyl-1,5-anhydro-6-bromo-2,6-dideoxy-5a-carba-DL-arabino-hex-1-enitol

3,4-di-O-acetyl-2,6-dibromo-2,6-dideoxy-5a-carba-β-DL-glucopyranosyl bromide

Downstream raw materials:

DL-3,4-di-O-acetyl-(1,2,4/3,5)-5-benzoyloxymethyl-2-(p-toluenosulfonamido)-1,3,4-cycloxanetriol

DL-1,2-di-O-acetyl-(1,3/2,4)-3-benzoyloxymethyl-4-bromo-5-cyclohexene-1,2-diol

Benzoic acid (1R,4S,5S,6R)-5,6-diacetoxy-4-bromo-cyclohex-2-enylmethyl ester

DL-1,2-di-O-acetyl-(1,6/2,5)-3-benzoyloxymethyl-5,6-dibromo-3-cyclohexene-1,2-diol