DL-2,3-O-isopropylidene-(1,3/2,4,6)-6-benzoyloxymethyl-4-bromo-1,2,3-cyclohexanetriol

Base Information

• Chemical Name: DL-2,3-O-isopropylidene-(1,3/2,4,6)-6-benzoyloxymethyl-4-bromo-1,2,3-cyclohexanetriol
• CAS No.: 73411-02-6
• Molecular Formula: C₁₇H₂₁BrO₅
• Molecular Weight: 385.255

Synonyms:DL-2,3-O-isopropylidene-(1,3/2,4,6)-6-benzoyloxymethyl-4-bromo-1,2,3-cyclohexanetriol

Chemical Property of DL-2,3-O-isopropylidene-(1,3/2,4,6)-6-benzoyloxymethyl-4-bromo-1,2,3-cyclohexanetriol

Chemical Property:

Purity/Quality:

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Technology Process of DL-2,3-O-isopropylidene-(1,3/2,4,6)-6-benzoyloxymethyl-4-bromo-1,2,3-cyclohexanetriol

There total 2 articles about DL-2,3-O-isopropylidene-(1,3/2,4,6)-6-benzoyloxymethyl-4-bromo-1,2,3-cyclohexanetriol 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:

sodium benzoate (532-32-1) + DL-(1,3/2,4,6)-4-bromo-6-bromomethyl-1,2,3-cyclohexanetriol (73411-00-4) + 2,2-dimethoxy-propane (77-76-9) → DL-1,2-O-isopropylidene-(1,3/2,4,6)-6-benzoyloxymethyl-4-bromo-1,2,3-cyclohexanetriol (73609-40-2) + DL-2,3-O-isopropylidene-(1,3/2,4,6)-6-benzoyloxymethyl-4-bromo-1,2,3-cyclohexanetriol (73411-02-6) + DL-2,3-O-isopropylidene-(1,3/2,4)-4-benzoyloxymethyl-5-cyclohexene-1,2,3-triol

Guidance literature:

With toluene-4-sulfonic acid; Yield given. Multistep reaction. Yields of byproduct given; 1.) DMF, 70 deg C, 2 h, 2.) 90percent aq. DMF, from 70 deg C to 80 deg C, 6 h;

DOI:10.1246/bcsj.56.499

Reference yield:

sodium benzoate (532-32-1) + DL-(1,3/2,4,6)-4-bromo-6-bromomethyl-1,2,3-cyclohexanetriol (73411-00-4) + 2,2-dimethoxy-propane (77-76-9) → DL-1,2-O-isopropylidene-(1,3/2,4,6)-6-benzoyloxymethyl-4-bromo-1,2,3-cyclohexanetriol (73609-40-2) + DL-2,3-O-isopropylidene-(1,3/2,4,6)-6-benzoyloxymethyl-4-bromo-1,2,3-cyclohexanetriol (73411-02-6)

Guidance literature:

With toluene-4-sulfonic acid; Multistep reaction. Yields of byproduct given; 1.) DMF, 60 deg C, 2 h; 2.) aq. DMF, 70 deg C, 6 h;

DOI:10.1246/cl.1980.139

Reference yield: 73.0%

DL-2,3-O-isopropylidene-(1,3/2,4,6)-6-benzoyloxymethyl-4-bromo-1,2,3-cyclohexanetriol (73411-02-6) → DL-2,3-O-isopropylidene-(1,3,4/2,6)-4-azido-6-benzoyloxymethyl-1,2,3-cyclohexanetriol

Guidance literature:

With sodium azide; In dimethyl sulfoxide; at 120 ℃; for 18h;

DOI:10.1246/bcsj.56.499

upstream raw materials:

sodium benzoate

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

2,2-dimethoxy-propane

Downstream raw materials:

(2R,3R,4S,5S,6R)-2-((1R,2R,3S,4S,6R)-4-Amino-2,3-dihydroxy-6-hydroxymethyl-cyclohexyloxy)-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol; hydrochloride

(2R,3R,4S,5S,6R)-2-((1S,2S,3R,4R,6S)-4-Amino-2,3-dihydroxy-6-hydroxymethyl-cyclohexyloxy)-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol; hydrochloride

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