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Good quantity D-Pinitol Basic information Product Name: D-Pinitol Synonyms: PINITOL;3-O-METHYL-D-CHIRO-INOSITOL;D-PINITOL;D-chiro-Inositol, 3-O-methyl-;D-PINTIOL;D-Pinitol 98.0%min;Pin
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(1R,2R,3R,4S,5R,6S)-2,3,6-trihydroxy-4,5-di-O-isopropylidene-1-O-methylcyclohexane
pinitol
Conditions | Yield |
---|---|
With hydrogenchloride In water; acetone for 0.5h; Ambient temperature; | 100% |
With hydrogenchloride In water; acetone |
(1L-1,2-di-O-benzoyl-4-O-methyl-chiro-inosityloxy)-(l)-menthoxyacetate
pinitol
Conditions | Yield |
---|---|
With water; triethylamine In methanol for 68h; Ambient temperature; | 100% |
3,5-di-O-benzyl-D-pinitol
pinitol
Conditions | Yield |
---|---|
With hydrogen; palladium on activated charcoal In methanol | 100% |
(3aR,4S,5R,7aS)-5-methoxy-2,2-dimethyl-3a,4,5,7a-tetrahydrobenzo[d][1,3]dioxol-4-ol
pinitol
Conditions | Yield |
---|---|
With osmium(VIII) oxide; 4-methylmorpholine N-oxide In tetrahydrofuran; water; acetone at 20℃; for 24h; Inert atmosphere; Reflux; | 84% |
(1R,2S,3R,4S,5R,6S)-5,6-Bis-benzyloxy-3-methoxy-cyclohexane-1,2,4-triol
pinitol
Conditions | Yield |
---|---|
With hydrogen; palladium on activated charcoal In methanol for 24h; | 69% |
methanol
(1R,2S,3R,4S,5R,6S)-3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-7-oxa-bicyclo[4.1.0]heptane-2,5-diol
pinitol
Conditions | Yield |
---|---|
With trifluoroacetic acid In methanol | 60% |
D-myo-inositol
B
(1R,2S,3R,4S,5S,6S)-6-methoxycyclohexane-1,2,3,4,5-pentol
C
pinitol
Conditions | Yield |
---|---|
In water for 48h; Product distribution; biosynthesis with Simmondsia chinensis, various time; |
(1R,2S,3R,4S,5S,6S)-6-methoxycyclohexane-1,2,3,4,5-pentol
A
D-myo-inositol
C
pinitol
Conditions | Yield |
---|---|
In water for 48h; Product distribution; biosynthesis with Simmondsia chinensis, various time; |
1D-5-O-(α-D-galactopyranosyl)-4-O-methyl-chiro-inositol
A
D-Galactose
B
pinitol
Conditions | Yield |
---|---|
With α-D-galactosidase Product distribution; |
1D-(1,2,3,4)-1,2-di-O-benzyl-4-O-methylcyclohex-5-ene-1,2,3,4-tetraol
pinitol
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: pyridine / CH2Cl2 / 0.5 h / 0 °C 2: aq. OsO4, Me3NO / acetone; 2-methyl-propan-2-ol / 48 h 3: 58 percent / benzene / 1 h / Ambient temperature 4: 91 percent / K2CO3 / methanol / 2 h / 60 °C 5: 69 percent / H2 / 10percent Pd/C / methanol / 24 h View Scheme |
Acetic acid (1S,2S,3S,4R,5S,6R)-2,3-bis-benzyloxy-4,5-dihydroxy-6-methoxy-cyclohexyl ester
pinitol
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 91 percent / K2CO3 / methanol / 2 h / 60 °C 2: 69 percent / H2 / 10percent Pd/C / methanol / 24 h View Scheme |
pinitol
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: 79 percent / NaOMe / methanol / 4 h / 60 °C 2: pyridine / CH2Cl2 / 0.5 h / 0 °C 3: aq. OsO4, Me3NO / acetone; 2-methyl-propan-2-ol / 48 h 4: 58 percent / benzene / 1 h / Ambient temperature 5: 91 percent / K2CO3 / methanol / 2 h / 60 °C 6: 69 percent / H2 / 10percent Pd/C / methanol / 24 h View Scheme |
pinitol
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: aq. OsO4, Me3NO / acetone; 2-methyl-propan-2-ol / 48 h 2: 58 percent / benzene / 1 h / Ambient temperature 3: 91 percent / K2CO3 / methanol / 2 h / 60 °C 4: 69 percent / H2 / 10percent Pd/C / methanol / 24 h View Scheme |
Trifluoro-methanesulfonic acid (1R,2S,3S,4R,5S,6R)-2,3-bis-benzyloxy-4,5-dihydroxy-6-methoxy-cyclohexyl ester
pinitol
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 58 percent / benzene / 1 h / Ambient temperature 2: 91 percent / K2CO3 / methanol / 2 h / 60 °C 3: 69 percent / H2 / 10percent Pd/C / methanol / 24 h View Scheme |
(1S,2R,3R,4S,5R,6S)-2,3-dihydroxy-4,5-di-O-isopropylidene-7-oxabicyclo<4.1.0>heptane
pinitol
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 60 percent / Al2O3 / 24 h / Heating 2: 100 percent / conc. HCl / acetone; H2O / 0.5 h / Ambient temperature View Scheme | |
Multi-step reaction with 2 steps 1: 90 percent / Al2O3 2: HCl / H2O; acetone View Scheme |
(3aS,7aS)-4-bromo-2,2-dimethyl-3a,7a-dihydro-1,3-benzodioxole
pinitol
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: 97 percent / OsO4, N-methylmorpholine-N-oxide / acetone; H2O; 2-methyl-propan-2-ol / 8 h / Ambient temperature 2: 90 percent / LiAlH4 / tetrahydrofuran / 8 h / Ambient temperature 3: 88 percent / mCPBA / CH2Cl2 / 24 h / Ambient temperature 4: 60 percent / Al2O3 / 24 h / Heating 5: 100 percent / conc. HCl / acetone; H2O / 0.5 h / Ambient temperature View Scheme | |
Multi-step reaction with 5 steps 1: 85 percent / OsO4, MNO / H2O; acetone 2: 85 percent / LiAlH4 / tetrahydrofuran 3: 86 percent / m-CPBA / CH2Cl2 4: 90 percent / Al2O3 5: HCl / H2O; acetone View Scheme |
(3aS,4R,5R,7aR)-2,2-dimethyl-3a,4,5,7a-tetrahydrobenzo[d][1,3]dioxole-4,5-diol
pinitol
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 88 percent / mCPBA / CH2Cl2 / 24 h / Ambient temperature 2: 60 percent / Al2O3 / 24 h / Heating 3: 100 percent / conc. HCl / acetone; H2O / 0.5 h / Ambient temperature View Scheme | |
Multi-step reaction with 3 steps 1: 86 percent / m-CPBA / CH2Cl2 2: 90 percent / Al2O3 3: HCl / H2O; acetone View Scheme |
(3aS,4R,5R,7aS)-7-bromo-2,2-dimethyl-3a,4,5,7a-tetrahydrobenzo[d][1,3]dioxole-4,5-diol
pinitol
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 90 percent / LiAlH4 / tetrahydrofuran / 8 h / Ambient temperature 2: 88 percent / mCPBA / CH2Cl2 / 24 h / Ambient temperature 3: 60 percent / Al2O3 / 24 h / Heating 4: 100 percent / conc. HCl / acetone; H2O / 0.5 h / Ambient temperature View Scheme | |
Multi-step reaction with 4 steps 1: 85 percent / LiAlH4 / tetrahydrofuran 2: 86 percent / m-CPBA / CH2Cl2 3: 90 percent / Al2O3 4: HCl / H2O; acetone View Scheme |
cis-1,2-dihydrocatechol
pinitol
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: imidazole / dimethylformamide 2: 32 percent / 1O2 / -80 °C / Irradiation 3: thiourea / methanol 4: 95 percent / MCPBA 5: 60 percent / CF3CO2H / methanol View Scheme | |
Multi-step reaction with 6 steps 1: 84 percent / DMAP / pyridine / 1.) 0 deg C, 2.5 h, 2.) RT 2: 73 percent / m-CPBA / CH2Cl2 / 22 h / Ambient temperature; pH 8 phosphate buffer 3: 100 percent / camphorsulfonic acid monohydrate / CHCl3 / 22.5 h / Ambient temperature 4: MAP / pyridine; CH2Cl2 / 48 h / Ambient temperature 5: 97 percent / osmium tetroxide, N-methylmorpholine-N-oxide / 2-methyl-propan-2-ol; tetrahydrofuran-d8; H2O / 120 h / Ambient temperature 6: 100 percent / triethylamine, water / methanol / 68 h / Ambient temperature View Scheme |
(5S,6R)-5,6-Bis-(tert-butyl-dimethyl-silanyloxy)-cyclohexa-1,3-diene
pinitol
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 32 percent / 1O2 / -80 °C / Irradiation 2: thiourea / methanol 3: 95 percent / MCPBA 4: 60 percent / CF3CO2H / methanol View Scheme |
pinitol
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 95 percent / MCPBA 2: 60 percent / CF3CO2H / methanol View Scheme |
(1S,4R,7R,8S)-7,8-Bis-(tert-butyl-dimethyl-silanyloxy)-2,3-dioxa-bicyclo[2.2.2]oct-5-ene
pinitol
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: thiourea / methanol 2: 95 percent / MCPBA 3: 60 percent / CF3CO2H / methanol View Scheme |
benzene
pinitol
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: oxidation by Pseudomonas putida strain 2: imidazole / dimethylformamide 3: 32 percent / 1O2 / -80 °C / Irradiation 4: thiourea / methanol 5: 95 percent / MCPBA 6: 60 percent / CF3CO2H / methanol View Scheme |
cis-3,5-cyclohexadiene-1,2-diol dibenzoate
pinitol
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: 73 percent / m-CPBA / CH2Cl2 / 22 h / Ambient temperature; pH 8 phosphate buffer 2: 100 percent / camphorsulfonic acid monohydrate / CHCl3 / 22.5 h / Ambient temperature 3: MAP / pyridine; CH2Cl2 / 48 h / Ambient temperature 4: 97 percent / osmium tetroxide, N-methylmorpholine-N-oxide / 2-methyl-propan-2-ol; tetrahydrofuran-d8; H2O / 120 h / Ambient temperature 5: 100 percent / triethylamine, water / methanol / 68 h / Ambient temperature View Scheme |
(1α,2β,3β,6β)-6-methoxy-4-cyclohexene-1,2,3-triol 2,3-dibenzoate
pinitol
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: MAP / pyridine; CH2Cl2 / 48 h / Ambient temperature 2: 97 percent / osmium tetroxide, N-methylmorpholine-N-oxide / 2-methyl-propan-2-ol; tetrahydrofuran-d8; H2O / 120 h / Ambient temperature 3: 100 percent / triethylamine, water / methanol / 68 h / Ambient temperature View Scheme |
(1α,2α,5β,6Sb)-5,6-epoxy-3-cyclohexene-1,2-diol dibenzoate
pinitol
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 100 percent / camphorsulfonic acid monohydrate / CHCl3 / 22.5 h / Ambient temperature 2: MAP / pyridine; CH2Cl2 / 48 h / Ambient temperature 3: 97 percent / osmium tetroxide, N-methylmorpholine-N-oxide / 2-methyl-propan-2-ol; tetrahydrofuran-d8; H2O / 120 h / Ambient temperature 4: 100 percent / triethylamine, water / methanol / 68 h / Ambient temperature View Scheme |
<1S-(1α,2β,5β,6β)>-<5,6-di(benzoyloxy)-2-methoxy-3-cyclohexen-1-yl> (l)-menthoxyacetate
pinitol
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 97 percent / osmium tetroxide, N-methylmorpholine-N-oxide / 2-methyl-propan-2-ol; tetrahydrofuran-d8; H2O / 120 h / Ambient temperature 2: 100 percent / triethylamine, water / methanol / 68 h / Ambient temperature View Scheme |
cis-(1S,2S)-1,2-dihydroxy-3-bromocyclohexa-3,5-diene
pinitol
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: 100 percent / p-TsOH 2: 85 percent / OsO4, MNO / H2O; acetone 3: 85 percent / LiAlH4 / tetrahydrofuran 4: 86 percent / m-CPBA / CH2Cl2 5: 90 percent / Al2O3 6: HCl / H2O; acetone View Scheme |
(1R,2S,3R,4S,5R,6R)-3,4-(isopropylidenedioxy)-5,6-epoxycyclohexane-1,2-diol
pinitol
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: sodium methylate / 24 h / Inert atmosphere; Reflux 2: osmium(VIII) oxide; 4-methylmorpholine N-oxide / tetrahydrofuran; water; acetone / 24 h / 20 °C / Inert atmosphere; Reflux View Scheme |
(-)-(1S)-1-{(4S,5S)-5-[(1S)-1-hydroxy-2-propenyl]-2,2-dimethyl-1,3-dioxolan-4-yl}-2-propen-1-ol
pinitol
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 18 h / Inert atmosphere; Reflux 1.2: 8 h / 20 °C / Inert atmosphere 2.1: sodium methylate / 24 h / Inert atmosphere; Reflux 3.1: osmium(VIII) oxide; 4-methylmorpholine N-oxide / tetrahydrofuran; water; acetone / 24 h / 20 °C / Inert atmosphere; Reflux View Scheme |
pinitol
benzoyl chloride
1D-1,2,3,5,6-penta-O-benzoyl-4-O-methyl-chiro-inositol
Conditions | Yield |
---|---|
With dmap In pyridine for 23h; Ambient temperature; | 97% |
pinitol
Conditions | Yield |
---|---|
With hydrogen bromide at 20 - 85℃; for 7h; Conversion of starting material; | 96% |
With hydrogenchloride at 20 - 85℃; for 50h; Conversion of starting material; | 94% |
With hydrogen iodide | 77% |
acetic anhydride
pinitol
(1R,2R,3R,4S,5R,6R)-2,3,4,6-tetrakis(acetyloxy)-5-methoxycyclohexyl acetate
Conditions | Yield |
---|---|
With pyridine; dmap at 20℃; | 93% |
With pyridine for 1.5h; Heating; | 85% |
2-Methoxypropene
pinitol
1,2:5,6-bis-O-(1-methylethylidene)-3-O-methyl-D-chiro-inositol
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide at 80 - 82℃; | 90% |
pinitol
2,2-dimethoxy-propane
1,2:5,6-bis-O-(1-methylethylidene)-3-O-methyl-D-chiro-inositol
Conditions | Yield |
---|---|
With magnesium sulfate; toluene-4-sulfonic acid In acetone at 20℃; for 16h; | 89% |
With toluene-4-sulfonic acid In acetone at 20℃; for 12h; | 87% |
With toluene-4-sulfonic acid In acetone at 20℃; | 86% |
Conditions | Yield |
---|---|
Stage #1: BOC-glycine With 1,1'-carbonyldiimidazole In acetonitrile at 20℃; for 0.166667h; Stage #2: pinitol With triethylamine In acetonitrile at 60℃; for 72h; | 75% |
pinitol
1D-1,5-dideoxy-1,5-difluoro-4-O-methyl-neo-inositol
Conditions | Yield |
---|---|
With (diethylamido)sulfur trifluoride 1.) from -50 deg C to 0 deg C, 1.5 h, 2.) RT, 2 h; | 47% |
pinitol
4-nitrophenyl-β-D-galactopyranoside
Conditions | Yield |
---|---|
With sodium phosphate buffer; β-galactosidase from Bacillus circulans (EC 3.2.1.23) In acetonitrile at 37℃; for 72h; pH=7.0; | A 45% B 7% |
pinitol
1,1,2,2-tetramethoxycyclohexane
4,5-O-(1',2'-dimethoxycyclohexane-1',2'-diyl)-3-O-methyl-D-chiro-inositol
Conditions | Yield |
---|---|
With (1S)-10-camphorsulfonic acid; trimethyl orthoformate In methanol at 70℃; for 24h; | 45% |
1,3-Dichloro-1,1,3,3-tetraisopropyldisiloxane
pinitol
Conditions | Yield |
---|---|
With 1H-imidazole; dmap In N,N-dimethyl-formamide at 20℃; for 2h; | 24% |
pinitol
(2R)-2r,3c,4t,6t-tetrahydroxy-5c-methoxy-cyclohexanone
Conditions | Yield |
---|---|
With platinum on activated charcoal; air | |
With oxygen; platinum on activated charcoal In water |
pinitol
1,2:5,6-bis-O-(1-methylethylidene)-3-O-methyl-D-chiro-inositol
Conditions | Yield |
---|---|
With hydrogenchloride; acetone | |
With sulfuric acid; acetone | |
With acetic acid; acetone; zinc(II) chloride |
chloro-trimethyl-silane
pinitol
(1R,2S,3R,4R,5S,6S)-1-Methoxy-2,3,4,5,6-pentakis-trimethylsilanyloxy-cyclohexane
Conditions | Yield |
---|---|
With 1,1,1,3,3,3-hexamethyl-disilazane In pyridine |
pinitol
Conditions | Yield |
---|---|
With water-d2; nickel at 90 - 95℃; for 10h; |
pinitol
2,2-dimethoxy-propane
A
1,2:4,5-di-O-isopropylidene-3-O-methyl-D-chiro-inositol
B
1,2:5,6-bis-O-(1-methylethylidene)-3-O-methyl-D-chiro-inositol
Conditions | Yield |
---|---|
With camphor-10-sulfonic acid In N,N-dimethyl-formamide at 60℃; for 16h; Yield given. Yields of byproduct given; |
pinitol
triethoxymethylbenzene
1D-4-O-methyl-chiro-inositol 1,2:5,6-di(ethyl orthobenzoate)
Conditions | Yield |
---|---|
toluene-4-sulfonic acid In N,N-dimethyl-formamide for 8h; Ambient temperature; |
pinitol
4-nitrophenyl-β-D-galactopyranoside
Conditions | Yield |
---|---|
With β-galactosidase from Thermoanaerobacter sp In phosphate buffer at 37℃; for 72h; pH=7.0; | A 50 % Chromat. B 50 % Chromat. |
pinitol
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: 89 percent / p-TsOH; MgSO4 / acetone / 16 h / 20 °C 2: 99 percent / pyridine / 24 h / 0 - 5 °C 3: 80.68 percent / aq. AcOH / 10 h / 80 °C 4: 73 percent / K2CO3 / methanol / 8 h / 20 °C 5: 68 percent / DBU / dimethylsulfoxide / 48 h / 100 °C View Scheme |
pinitol
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: 89 percent / p-TsOH; MgSO4 / acetone / 16 h / 20 °C 2: 99 percent / pyridine / 24 h / 0 - 5 °C 3: 80.68 percent / aq. AcOH / 10 h / 80 °C 4: 73 percent / K2CO3 / methanol / 8 h / 20 °C 5: 66 percent / DBU / dimethylsulfoxide / 48 h / 100 °C View Scheme |
pinitol
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: 89 percent / p-TsOH; MgSO4 / acetone / 16 h / 20 °C 2: 99 percent / pyridine / 24 h / 0 - 5 °C 3: 80.68 percent / aq. AcOH / 10 h / 80 °C 4: 73 percent / K2CO3 / methanol / 8 h / 20 °C 5: DBU / dimethylsulfoxide / 48 h / 100 °C View Scheme |
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