10284-63-6

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;Pinit;D-Pinitol,95%
• CAS NO: 10284-63-6
• Molecular Formula: C₇H₁₄O₆
• Molecular Weight: 194.18
• EINECS: 1312995-182-4
• Product Categories: Miscellaneous Natural Products;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract;reagent;standard substance;Miscellaneous
• Mol File: 10284-63-6.mol
• Article Data: 15

Chemical Properties

• Melting Point: 179-185 °C(lit.)
• Boiling Point: 250.62°C (rough estimate)
• Flash Point: 145.6 °C
• Appearance: white powder
• Density: 1.2501 (rough estimate)
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.5600 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 12.98±0.70(Predicted)
• Water Solubility: Soluble in water.
• CAS DataBase Reference: D-Pinitol(CAS DataBase Reference)
• NIST Chemistry Reference: D-Pinitol(10284-63-6)
• EPA Substance Registry System: D-Pinitol(10284-63-6)

Safety Data

• Hazard Codes: F,C
• Statements: 11-34
• Safety Statements: 22-24/25-45-36/37/39-26-16
• WGK Germany: 3
• Hazardous Substances Data: 10284-63-6(Hazardous Substances Data)

Usage

Chemical Properties

white powder

Uses

Different sources of media describe the Uses of 10284-63-6 differently. You can refer to the following data:
1. suitable for coupling carboxyl- or aldehyde-containing ligands
2. D-pinitol may be used as a starting material to prepare its azole nucleoside analogs. It may also be used in the preparation of 1D-1,5-dideoxy-1,5-difluoro-neo-inositol and 1D-1-deoxy-1-fluoro-myo-inositol.

General Description

D-pinitol, commonly found conifers, is an isomer of L-quebrachitol.

InChI:InChI=1/C7H14O6/c1-13-7-5(11)3(9)2(8)4(10)6(7)12/h2-12H,1H3/t2-,3-,4-,5-,6+,7+/m0/s1

Synthetic route

(1R,2R,3R,4S,5R,6S)-2,3,6-trihydroxy-4,5-di-O-isopropylidene-1-O-methylcyclohexane (130792-46-0) → pinitol (10284-63-6)

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 (124647-09-2, 124751-79-7) → pinitol (10284-63-6)

Conditions	Yield
With water; triethylamine In methanol for 68h; Ambient temperature;	100%

3,5-di-O-benzyl-D-pinitol (1044736-09-5) → pinitol (10284-63-6)

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 (1195550-95-8) → pinitol (10284-63-6)

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 (186388-12-5) → pinitol (10284-63-6)

Conditions	Yield
With hydrogen; palladium on activated charcoal In methanol for 24h;	69%

methanol (67-56-1) + (1R,2S,3R,4S,5R,6S)-3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-7-oxa-bicyclo[4.1.0]heptane-2,5-diol (125164-85-4) → pinitol (10284-63-6)

Conditions	Yield
With trifluoroacetic acid In methanol	60%

D-myo-inositol (87-89-8) → D-chiro-inositol (488-54-0, 488-55-1, 488-58-4, 488-59-5, 551-72-4, 576-63-6, 643-10-7, 643-12-9, 6917-35-7, 18685-70-6, 38876-99-2, 39907-99-8, 40461-73-2, 41546-32-1, 41546-33-2, 41546-34-3, 41546-35-4, 41546-36-5, 87-89-8) + (1R,2S,3R,4S,5S,6S)-6-methoxycyclohexane-1,2,3,4,5-pentol (6090-97-7) + pinitol (10284-63-6) + D-galacturonic acid

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 (6090-97-7) → D-myo-inositol (87-89-8) + D-chiro-inositol (488-54-0, 488-55-1, 488-58-4, 488-59-5, 551-72-4, 576-63-6, 643-10-7, 643-12-9, 6917-35-7, 18685-70-6, 38876-99-2, 39907-99-8, 40461-73-2, 41546-32-1, 41546-33-2, 41546-34-3, 41546-35-4, 41546-36-5, 87-89-8) + pinitol (10284-63-6) + D-galacturonic acid

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 (75589-40-1, 79391-03-0, 98168-33-3) → D-Galactose (59-23-4) + pinitol (10284-63-6)

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 (186382-59-2) → pinitol (10284-63-6)

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 (186382-61-6) → pinitol (10284-63-6)

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

(1S,2S,5S,6R)-5,6-Bis-benzyloxy-2-methoxy-3-tributylstannanyl-cyclohex-3-enol → pinitol (10284-63-6)

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

Trifluoro-methanesulfonic acid (1R,2R,5S,6S)-5,6-bis-benzyloxy-2-methoxy-cyclohex-3-enyl ester → pinitol (10284-63-6)

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 (186382-60-5) → pinitol (10284-63-6)

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 (130669-73-7) → pinitol (10284-63-6)

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 (130669-75-9) → pinitol (10284-63-6)

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 (130669-76-0) → pinitol (10284-63-6)

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 (137501-12-3, 130669-72-6) → pinitol (10284-63-6)

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 (17793-95-2) → pinitol (10284-63-6)

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 (125164-82-1) → pinitol (10284-63-6)

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

(1S,4R,5S,6R)-5,6-Bis-(tert-butyl-dimethyl-silanyloxy)-cyclohex-2-ene-1,4-diol → pinitol (10284-63-6)

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 (125164-83-2) → pinitol (10284-63-6)

Conditions	Yield
Multi-step reaction with 3 steps 1: thiourea / methanol 2: 95 percent / MCPBA 3: 60 percent / CF3CO2H / methanol View Scheme

benzene (71-43-2) → pinitol (10284-63-6)

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 (86504-06-5) → pinitol (10284-63-6)

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 (111015-72-6, 124751-83-3) → pinitol (10284-63-6)

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 (111015-71-5, 111059-10-0) → pinitol (10284-63-6)

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 (124647-08-1) → pinitol (10284-63-6)

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 (67451-62-1, 82683-92-9, 132958-32-8, 130792-45-9) → pinitol (10284-63-6)

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 (145107-28-4) → pinitol (10284-63-6)

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 (261631-95-2) → pinitol (10284-63-6)

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 (10284-63-6) + benzoyl chloride (98-88-4) → 1D-1,2,3,5,6-penta-O-benzoyl-4-O-methyl-chiro-inositol (73803-10-8)

Conditions	Yield
With dmap In pyridine for 23h; Ambient temperature;	97%

pinitol (10284-63-6) → D-chiro-inositol

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 (108-24-7) + pinitol (10284-63-6) → (1R,2R,3R,4S,5R,6R)-2,3,4,6-tetrakis(acetyloxy)-5-methoxycyclohexyl acetate (42442-75-1)

Conditions	Yield
With pyridine; dmap at 20℃;	93%
With pyridine for 1.5h; Heating;	85%

2-Methoxypropene (116-11-0) + pinitol (10284-63-6) → 1,2:5,6-bis-O-(1-methylethylidene)-3-O-methyl-D-chiro-inositol (57819-56-4)

Conditions	Yield
In N,N-dimethyl-formamide at 80 - 82℃;	90%

pinitol (10284-63-6) + 2,2-dimethoxy-propane (77-76-9) → 1,2:5,6-bis-O-(1-methylethylidene)-3-O-methyl-D-chiro-inositol (57819-56-4)

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%

BOC-glycine (4530-20-5) + pinitol (10284-63-6) → 1,2,4,5,6-pentakis-O-(Boc-Gly)-3-O-methyl-D-chiro-inositol

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 (10284-63-6) → 1D-1,5-dideoxy-1,5-difluoro-4-O-methyl-neo-inositol (127002-20-4)

Conditions	Yield
With (diethylamido)sulfur trifluoride 1.) from -50 deg C to 0 deg C, 1.5 h, 2.) RT, 2 h;	47%

pinitol (10284-63-6) + 4-nitrophenyl-β-D-galactopyranoside (3150-24-1) → 1D-1-O-(β-D-Galactopyranosyl)-4-O-methyl-chiro-inositol + 1D-1-O-(β-D-Galactopyranosyl-(1->4)-O-β-D-galactopyranosyl)-4-O-methyl-chiro-inositol

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 (10284-63-6) + 1,1,2,2-tetramethoxycyclohexane (163125-34-6) → 4,5-O-(1',2'-dimethoxycyclohexane-1',2'-diyl)-3-O-methyl-D-chiro-inositol (434335-30-5)

Conditions	Yield
With (1S)-10-camphorsulfonic acid; trimethyl orthoformate In methanol at 70℃; for 24h;	45%

1,3-Dichloro-1,1,3,3-tetraisopropyldisiloxane (69304-37-6) + pinitol (10284-63-6) → 3-O-methyl-4,5-O-(tetraisopropyldisiloxane-1',3'-diyl)-D-chiro-inositol

Conditions	Yield
With 1H-imidazole; dmap In N,N-dimethyl-formamide at 20℃; for 2h;	24%

pinitol (10284-63-6) → (2R)-2r,3c,4t,6t-tetrahydroxy-5c-methoxy-cyclohexanone (3559-01-1, 5834-35-5, 20095-97-0, 92541-30-5, 92541-35-0, 92541-36-1)

Conditions	Yield
With platinum on activated charcoal; air
With oxygen; platinum on activated charcoal In water

pinitol (10284-63-6) → 1,2:5,6-bis-O-(1-methylethylidene)-3-O-methyl-D-chiro-inositol (57819-56-4)

Conditions	Yield
With hydrogenchloride; acetone
With sulfuric acid; acetone
With acetic acid; acetone; zinc(II) chloride

chloro-trimethyl-silane (75-77-4) + pinitol (10284-63-6) → (1R,2S,3R,4R,5S,6S)-1-Methoxy-2,3,4,5,6-pentakis-trimethylsilanyloxy-cyclohexane (14199-75-8, 14199-76-9, 14313-39-4, 14486-18-1, 75658-14-9, 92419-60-8, 92620-07-0, 92620-08-1, 92620-09-2, 92620-10-5, 92620-11-6)

Conditions	Yield
With 1,1,1,3,3,3-hexamethyl-disilazane In pyridine

pinitol (10284-63-6) → deruterised chiro inositol

Conditions	Yield
With water-d2; nickel at 90 - 95℃; for 10h;

pinitol (10284-63-6) + 2,2-dimethoxy-propane (77-76-9) → 1,2:4,5-di-O-isopropylidene-3-O-methyl-D-chiro-inositol (58706-05-1, 96744-20-6, 127062-83-3) + 1,2:5,6-bis-O-(1-methylethylidene)-3-O-methyl-D-chiro-inositol (57819-56-4)

Conditions	Yield
With camphor-10-sulfonic acid In N,N-dimethyl-formamide at 60℃; for 16h; Yield given. Yields of byproduct given;

pinitol (10284-63-6) + triethoxymethylbenzene (1663-61-2) → 1D-4-O-methyl-chiro-inositol 1,2:5,6-di(ethyl orthobenzoate) (78077-12-0)

Conditions	Yield
toluene-4-sulfonic acid In N,N-dimethyl-formamide for 8h; Ambient temperature;

pinitol (10284-63-6) + 4-nitrophenyl-β-D-galactopyranoside (3150-24-1) → 1D-1-O-(β-D-Galactopyranosyl)-4-O-methyl-chiro-inositol + 1D-1-O-(β-D-galactopyranosyl)-3-O-methyl-chiro-inisitol

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 (10284-63-6) → (1'S,2'S,3'S,4'S,5'R,6'R)-3'-O-methyl-5'-deoxy-5'-(benzotriazole-1-yl)-D-chiro-inositol

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 (10284-63-6) → (1'S,2'S,3'S,4'S,5'R,6'R)-3'-O-methyl-5'-deoxy-5'-(6-nitroindazole-1-yl)-D-chiro-inositol

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 (10284-63-6) → (1'S,2'S,3'S,4'S,5'R,6'R)-3'-O-methyl-5'-deoxy-5'-(5-nitroindazole-1-yl)-D-chiro-inositol

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

Upstream product

• 85716-44-5 methyl 2,3,4-tri-O-benzyl-α-d-xylo-hex-5-enopyranoside 
• 85716-43-4 methyl 6-deoxy-6-iodo-2,3,4-tri-O-benzyl-α-D-glucopyranoside 
• 18311-26-7 methyl 6-O-trityl-α-D-glucopyranoside 
• 111015-72-6 (1α,2β,3β,6β)-6-methoxy-4-cyclohexene-1,2,3-triol 2,3-dibenzoate 
• 111015-73-7 DL-1,2-di-O-methyl-chiro-inositol 
• 98925-52-1 (+/-)-5,6-di-O-allyl-1,4-di-O-benzyl-myo-inositol 
• 98906-32-2 (±)-1,4-di-O-allyl-2,3:5,6-di-O-isopropylidene-myo-inositol 
• 51548-88-0 (+/-)-1,2:4,5-di-O-isopropylidene-myo-inositol 
• 80971-02-4 (1S,2S,3R,4S,5S,6R)-3,4,6-Tris-benzyloxy-5-methoxy-cyclohexane-1,2-diol 
• 87-89-8 D-myo-inositol 
• 77-78-1 dimethyl sulfate 
• 97-30-3 methyl-alpha-D-glucopyranoside 
• 133218-74-3 4,5,6-tri-O-benzyl-1,2-anhydro-myo-inositol 
• 102997-58-0 (1R,2R,3S)-tris(phenylmethoxy)-6S-hydroxy-cyclohex-4-ene 

Downstream Products

• 127002-20-4 1D-1,5-dideoxy-1,5-difluoro-4-O-methyl-neo-inositol 
• 14199-75-8 (1R,2S,3R,4R,5S,6S)-1-Methoxy-2,3,4,5,6-pentakis-trimethylsilanyloxy-cyclohexane 
• 73803-10-8 1D-1,2,4,5,6-penta-O-benzoyl-3-O-methyl-chiro-inositol 
• 1158414-99-3 1D-3-O-methyl-1,2,4,5,6-penta-O-propanoyl-chiro-inositol 
• 1158415-00-9 (1R,2R,3R,4S,5R,6R)-2,3,4,6-tetrakis(butanoyloxy)-5-methoxycyclohexyl butanoate 

Related news

GC–MS analysis of D-Pinitol (cas 10284-63-6) in carob: Syrup and fruit (flesh and seed)07/26/2019

D-pinitol (3-O-methyl-D-chiro-inositol) is a well-known bioactive compound with anti-diabetic and anti-oxidant biological functions. A gas chromatography–mass spectrometry (GC–MS) method was developed for its quantitation in carob syrup, flesh and seed samples originated from Cyprus. The analy...detailed

Relevant articles and documents

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A C 2-symmetric chiral pool-based flexible strategy: Synthesis of (+)- and (-)-shikimic acids, (+)- and (-)-4- epi -shikimic acids, and (+)- and (-)-pinitol

Via combination of a novel acid-promoted rearrangement of acetal functionality with the controlled installation of the epoxide unit to create the pivotal epoxide intermediates in enantiomerically pure form, a simple, concise, flexible, and readily scalable enantiodivergent synthesis of (+)- and (-)-shikimic acids and (+)- and (-)-4-epi-shikimic acids has emerged. This simple strategy not only provides an efficient approach to shikimic acids but also can readily be adopted for the synthesis of (+)- and (-)-pinitols. These concise total syntheses exemplify the use of pivotal allylic epoxide 14 and its enantiomer ent-14. A readily available inexpensive C2-symmetric l-tartaric acid (7) served as key precursor. In general, the strategy here provides a neat example of the use of a four-carbon chiron and offers a good account of the synthesis of functionalized cyclohexane targets.

Stereoselective oxidation of protected inositol derivatives catalyzed by inositol dehydrogenase from Bacillus subtilis

Inositol dehydrogenase (EC 1.1.1.18) from Bacillus subtilis is shown to have a nonpolar cavity adjacent to the active site, allowing racemic protected inositol derivatives such as 4-O-benzyl-myo-inositol to be recognized with very high apparent stereoselectivity.

Total synthesis of (+)-pinitol

A new synthesis of (+)-pinitol 9 has been developed starting from the 7-oxanorbornenic sulfone (+)-5, prepared in enantiomerically pure form by resolution of the sulfonyl-7-oxanorbornanol 4. These precursors are available from the Diels-Alder adduct of furan and trans-1,2-bis-(phenylsulfonyl)-ethylene.