DL-(1,2,3,5/4,6)- and DL-(1,2,4/3,5,6)-2,3,4,5,6-Penta-O-benzyl-2,3,4,5,6-pentahydroxycyclohexane-1-methanol

Base Information

Chemical Name:DL-(1,2,3,5/4,6)- and DL-(1,2,4/3,5,6)-2,3,4,5,6-Penta-O-benzyl-2,3,4,5,6-pentahydroxycyclohexane-1-methanol
CAS No.:97292-73-4
Molecular Formula:C₄₂H₄₄O₆
Molecular Weight:644.808
Hs Code.:

Synonyms:

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Chemical Property of DL-(1,2,3,5/4,6)- and DL-(1,2,4/3,5,6)-2,3,4,5,6-Penta-O-benzyl-2,3,4,5,6-pentahydroxycyclohexane-1-methanol

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Technology Process of DL-(1,2,3,5/4,6)- and DL-(1,2,4/3,5,6)-2,3,4,5,6-Penta-O-benzyl-2,3,4,5,6-pentahydroxycyclohexane-1-methanol

There total 9 articles about DL-(1,2,3,5/4,6)- and DL-(1,2,4/3,5,6)-2,3,4,5,6-Penta-O-benzyl-2,3,4,5,6-pentahydroxycyclohexane-1-methanol 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:

: 87-89-8
D-myo-inositol

: 97292-73-4,130404-37-4
DL-(1,2,3,5/4,6)- and DL-(1,2,4/3,5,6)-2,3,4,5,6-Penta-O-benzyl-2,3,4,5,6-pentahydroxycyclohexane-1-methanol

Guidance literature:: Multi-step reaction with 9 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

9: 1.) BH₃*Me₂S; 2.) 5M NaOH, 30percent H₂O₂ / 1.) toluene, 60 deg C, 1 h; 2.) 50 deg C, 1 h

With potassium hydroxide; sodium hydroxide; n-butyllithium; dimethylsulfide borane complex; dihydrogen peroxide; 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

: 97292-73-4,130404-37-4
DL-(1,2,3,5/4,6)- and DL-(1,2,4/3,5,6)-2,3,4,5,6-Penta-O-benzyl-2,3,4,5,6-pentahydroxycyclohexane-1-methanol

Guidance literature:: Multi-step reaction with 8 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

8: 1.) BH₃*Me₂S; 2.) 5M NaOH, 30percent H₂O₂ / 1.) toluene, 60 deg C, 1 h; 2.) 50 deg C, 1 h

With potassium hydroxide; sodium hydroxide; n-butyllithium; dimethylsulfide borane complex; dihydrogen peroxide; 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

Reference yield:

: 10583-42-3,64681-25-0,64681-27-2,64681-28-3,111466-10-5,111466-15-0,132437-50-4,132437-54-8,135267-01-5,135355-09-8,138923-08-7,138923-09-8,144068-89-3
(+/-)-1-O-allyl-3,4,5,6-tetrakis-O-benzyl myo-inositol

: 97292-73-4,130404-37-4
DL-(1,2,3,5/4,6)- and DL-(1,2,4/3,5,6)-2,3,4,5,6-Penta-O-benzyl-2,3,4,5,6-pentahydroxycyclohexane-1-methanol

Guidance literature:: Multi-step reaction with 5 steps

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

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

3: 72 percent / pyridinium chlorochromate / CH₂Cl₂ / 24 h / 25 °C

4: 98 percent / BuLi / tetrahydrofuran / 1 h / 1 - 25 °C

5: 1.) BH₃*Me₂S; 2.) 5M NaOH, 30percent H₂O₂ / 1.) toluene, 60 deg C, 1 h; 2.) 50 deg C, 1 h

With sodium hydroxide; n-butyllithium; dimethylsulfide borane complex; dihydrogen peroxide; sodium hydride; toluene-4-sulfonic acid; pyridinium chlorochromate; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1002/hlca.19900730428