DL-1,2,3,4,5-Penta-O-benzyl-6-methylidenecyclohexane-1,2,4/3,5-pentol

Base Information

Chemical Name:DL-1,2,3,4,5-Penta-O-benzyl-6-methylidenecyclohexane-1,2,4/3,5-pentol
CAS No.:130277-48-4
Molecular Formula:C₄₂H₄₂O₅
Molecular Weight:626.792
Hs Code.:

Synonyms:DL-1,2,3,4,5-Penta-O-benzyl-6-methylidenecyclohexane-1,2,4/3,5-pentol

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Chemical Property of DL-1,2,3,4,5-Penta-O-benzyl-6-methylidenecyclohexane-1,2,4/3,5-pentol

Chemical Property:

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Technology Process of DL-1,2,3,4,5-Penta-O-benzyl-6-methylidenecyclohexane-1,2,4/3,5-pentol

There total 8 articles about DL-1,2,3,4,5-Penta-O-benzyl-6-methylidenecyclohexane-1,2,4/3,5-pentol 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: 98.0%

: 1779-49-3
Methyltriphenylphosphonium bromide

: 22144-57-6,97371-73-8
DL-2,3,4,5,6-Penta-O-benzyl-2,3,5/4,6-pentahydroxycyclohexanone

: 130277-48-4
DL-1,2,3,4,5-Penta-O-benzyl-6-methylidenecyclohexane-1,2,4/3,5-pentol

Guidance literature:: With n-butyllithium; In tetrahydrofuran; at 1 - 25 ℃; for 1h;
DOI:10.1002/hlca.19900730428

Reference yield:

: 87-89-8
D-myo-inositol

: 130277-48-4
DL-1,2,3,4,5-Penta-O-benzyl-6-methylidenecyclohexane-1,2,4/3,5-pentol

Guidance literature:: Multi-step reaction with 8 steps

1: 93 percent / TsOH / toluene; dimethylformamide / 9 h / Heating

2: 183 g / KOH / 0.5 h / 120 °C

3: 85 percent / AcOH / H₂O / 1.5 h / 80 - 100 °C

4: 1.) Bu₂SnO / 1.) toluene, 110 deg C; 2.) DMF, 80 deg C

5: NaH / dimethylformamide / 4 h / 40 °C

6: TsOH / 5percent Pd/C / aq. ethanol / 22 h / Heating

7: 72 percent / pyridinium chlorochromate / CH₂Cl₂ / 24 h / 25 °C

8: 98 percent / BuLi / tetrahydrofuran / 1 h / 1 - 25 °C

With potassium hydroxide; n-butyllithium; sodium hydride; di(n-butyl)tin oxide; toluene-4-sulfonic acid; acetic acid; pyridinium chlorochromate; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; water; N,N-dimethyl-formamide; toluene;
DOI:10.1002/hlca.19900730428

Reference yield:

: 6763-47-9,1251832-23-1
rac-1,2-O-cyclohexylidene-myo-inositol

: 130277-48-4
DL-1,2,3,4,5-Penta-O-benzyl-6-methylidenecyclohexane-1,2,4/3,5-pentol

Guidance literature:: Multi-step reaction with 7 steps

1: 183 g / KOH / 0.5 h / 120 °C

2: 85 percent / AcOH / H₂O / 1.5 h / 80 - 100 °C

3: 1.) Bu₂SnO / 1.) toluene, 110 deg C; 2.) DMF, 80 deg C

4: NaH / dimethylformamide / 4 h / 40 °C

5: TsOH / 5percent Pd/C / aq. ethanol / 22 h / Heating

6: 72 percent / pyridinium chlorochromate / CH₂Cl₂ / 24 h / 25 °C

7: 98 percent / BuLi / tetrahydrofuran / 1 h / 1 - 25 °C

With potassium hydroxide; n-butyllithium; sodium hydride; di(n-butyl)tin oxide; toluene-4-sulfonic acid; acetic acid; pyridinium chlorochromate; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1002/hlca.19900730428