DL-5,6-di-O-acetyl-1,2:3,4-dianhydro-(1,2,6/3,4,5)-1-C-benzoyloxymethyl-1,2,3,4,5,6-cyclohexanehexol

Base Information

Chemical Name:DL-5,6-di-O-acetyl-1,2:3,4-dianhydro-(1,2,6/3,4,5)-1-C-benzoyloxymethyl-1,2,3,4,5,6-cyclohexanehexol
CAS No.:58072-91-6
Molecular Formula:C₁₈H₁₈O₈
Molecular Weight:362.336
Hs Code.:

Synonyms:

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Chemical Property of DL-5,6-di-O-acetyl-1,2:3,4-dianhydro-(1,2,6/3,4,5)-1-C-benzoyloxymethyl-1,2,3,4,5,6-cyclohexanehexol

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Technology Process of DL-5,6-di-O-acetyl-1,2:3,4-dianhydro-(1,2,6/3,4,5)-1-C-benzoyloxymethyl-1,2,3,4,5,6-cyclohexanehexol

There total 34 articles about DL-5,6-di-O-acetyl-1,2:3,4-dianhydro-(1,2,6/3,4,5)-1-C-benzoyloxymethyl-1,2,3,4,5,6-cyclohexanehexol 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: 100.0%

: 108-24-7
acetic anhydride

: 175979-34-7
4-benzoyloxymethyl-3,8-dioxatricyclo[5.1.0.0^2,4]octane-5,6-diol 5-acetate

: 58072-91-6,58690-93-0,58690-94-1,74081-48-4,20421-13-0
(+)-crotepoxide

Guidance literature:: With dmap; triethylamine; In dichloromethane; for 12h; Ambient temperature;
DOI:10.1021/jo970907o

Reference yield: 20.0%

: 74766-85-1,86782-19-6
trans-2,3-diacetoxy-1-[(benzoyloxy)methyl]-cyclohexa-4,6-diene

: 20421-13-0,58072-91-6,58690-93-0,58690-94-1,74081-48-4
DL-5,6-di-O-acetyl-1,2:3,4-dianhydro-(1,2,6/3,4,5)-1-C-benzoyloxymethyl-1,2,3,4,5,6-cyclohexanehexol

Guidance literature:: With 2,6-di-tert-butyl-4-methyl-phenol; 3-chloro-benzenecarboperoxoic acid; for 1.5h; Heating;
DOI:10.1246/bcsj.56.1710

Reference yield:

: 98-88-4
benzoyl chloride

: 58072-91-6,58690-93-0,58690-94-1,74081-48-4,20421-13-0
(+)-crotepoxide

Guidance literature:: Multi-step reaction with 11 steps

1: 82 percent / collidine / CH₂Cl₂ / 2 h / -78 - 25 °C

2: 97 percent / imidazole, DMAP / CH₂Cl₂ / 12 h / Ambient temperature

3: 75 percent / RuCl₃, NaIO₄ / ethyl acetate; acetonitrile / 0.05 h / 0 °C

4: 97 percent / DMAP / pyridine; CH₂Cl₂ / 12 h / Ambient temperature

5: 89 percent / SO₂Cl₂ / pyridine; CH₂Cl₂ / 2.5 h / 0 °C

6: 80 percent / TFA / H₂O; CH₂Cl₂ / 6 h / Ambient temperature

7: 1.) 1,1'-thiocarbonyldiimidazole, 2.) P(OMe)3 / 1.) TolH, reflux, 24 h, 2.) reflux, 24 h

8: 80 percent / aq. HF / acetonitrile / 6 h / Ambient temperature

9: 48 percent / O₂, TPP / CCl₄ / 7 h / Irradiation

10: CoTPP / CHCl₃ / 3 h / 0 °C

11: 100 percent / Et₃N, DMAP / CH₂Cl₂ / 12 h / Ambient temperature

With 1H-imidazole; 2,3,5-trimethyl-pyridine; dmap; ruthenium trichloride; sodium periodate; sulfuryl dichloride; hydrogen fluoride; oxygen; thiamine diphosphate; triethylamine; 1,1'-Thiocarbonyldiimidazole; trifluoroacetic acid; phosphorous acid trimethyl ester; In pyridine; tetrachloromethane; dichloromethane; chloroform; water; ethyl acetate; acetonitrile;
DOI:10.1021/jo970907o