642-38-6

Basic information

• Product Name: L-QUEBRACHITOL
• Synonyms: L-CHIRO-INOSITOL 2-METHYL ETHER;L-QUEBRACHITOL;1L-2-O-METHYL-CHIRO-INOSITOL;2-O-METHYL-L-CHIRO-INOSITOL;2-O-METHYL-1,2,4/3,5,6-HEXAHYDROXYCYCLOHEXANE;3-O-METHYL-L-CHIRO-INOSITOL;(-)-QUEBRACHITOL;QUEBRACHITOL
• CAS NO: 642-38-6
• Molecular Formula: C₇H₁₄O₆
• Molecular Weight: 194.18
• Product Categories: Miscellaneous Natural Products
• Mol File: 642-38-6.mol
• Article Data: 7

Chemical Properties

• Melting Point: 190-198 °C
• Boiling Point: 250.62°C (rough estimate)
• Flash Point: 145.6 °C
• Appearance: white to off-white crystals
• Density: 1.56±0.1 g/cm3 (20 ºC 760 Torr)
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.572
• Storage Temp.: 2-8°C
• Solubility: DMSO (Slightly), Water (Sparingly)
• PKA: 12.98±0.70(Predicted)
• CAS DataBase Reference: L-QUEBRACHITOL(CAS DataBase Reference)
• NIST Chemistry Reference: L-QUEBRACHITOL(642-38-6)
• EPA Substance Registry System: L-QUEBRACHITOL(642-38-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 24/25-36-26
• Hazardous Substances Data: 642-38-6(Hazardous Substances Data)

Usage

Chemical Properties

white to off-white powder

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

2-Methoxypropene (116-11-0) + quebrachitol (642-38-6) → 1L-3,4,:5,6-di-O-isopropylidene-2-O-methyl-chiro-inositol (58769-23-6)

Conditions	Yield
With hydrogenchloride In N,N-dimethyl-formamide at 60℃; for 2h;	96%
camphor-10-sulfonic acid In N,N-dimethyl-formamide at 20 - 60℃; for 5h; Cyclization;	91%
With camphor-10-sulfonic acid In N,N-dimethyl-formamide at 60℃; for 4h;	85%

quebrachitol (642-38-6) → 1L-chiro-inositol (38876-99-2)

Conditions	Yield
With hydrogen iodide	93%
With hydrogen iodide for 2h; Heating;	80%
With hydrogen iodide

quebrachitol (642-38-6) + benzoyl chloride (98-88-4) → L-1,3,4,5,6-penta-O-benzoyl-2-O-methyl-chiro-inositol (73803-06-2)

Conditions	Yield
With pyridine at 80 - 90℃; for 6h;	89%
With dmap In pyridine at 20℃; Acylation;

quebrachitol (642-38-6) + 2,2-dimethoxy-propane (77-76-9) → 1L-3,4,:5,6-di-O-isopropylidene-2-O-methyl-chiro-inositol (58769-23-6) + 1L-5,6-O-Isopropyliden-2-O-methyl-chiro-inosit (17230-37-4)

Conditions	Yield
With toluene-4-sulfonic acid In N,N-dimethyl-formamide at 80℃; for 20h;	A 85% B 10%
With toluene-4-sulfonic acid In N,N-dimethyl-formamide for 16h; Ambient temperature;	A 6.9 g B n/a

cycloxexanone dimethyl ketal (933-40-4) + quebrachitol (642-38-6) → L-3,4:5.6-di-O-cyclohexylidene-2-O-methyl-(-)-chiro-inositol (6848-53-9) + 1L-1,2-O-cyclohexylidene-5-O-methyl-chiro-inositol (754197-57-4)

Conditions	Yield
With toluene-4-sulfonic acid In N,N-dimethyl-formamide at 20 - 105℃; for 22.5h;	A 71% B 9%

quebrachitol (642-38-6) + benzyl bromide (100-39-0) → C42H44O6

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide	55%

quebrachitol (642-38-6) → (1S,2S,3R,4S,5S,6S)-1-fluoro-2-O-(methyl)cyclohexane-2,3,4,5,6-pentol (125290-99-5)

Conditions	Yield
With 4,4'-diaminostilbene-2,2'-disulfonic acid In dichloromethane at -30 - 20℃;	54%
With (diethylamido)sulfur trifluoride In dichloromethane 1.) -40 dec C to -30 deg C, 30 min, 2.) -20 deg C, 2.5 h, 3.) 0 deg C, 2.8 h then r.t., 30 min;	53%
With diethylamino-sulfur trifluoride In dichloromethane at 20℃; for 4h;

quebrachitol (642-38-6) + benzoyl chloride (98-88-4) → C21H22O8 + C21H22O8 + C28H26O9 (341524-05-8)

Conditions	Yield
With pyridine at 0 - 10℃; for 6h;	A 20% B 20% C 50%

quebrachitol (642-38-6) + benzoyl chloride (98-88-4) → L-1,3,4,5,6-penta-O-benzoyl-2-O-methyl-chiro-inositol (73803-06-2) + C28H26O9 (341524-05-8) + C35H30O10 (341524-06-9)

Conditions	Yield
With pyridine at 0 - 10℃; for 6h;	A 20% B 20% C 40%

quebrachitol (642-38-6) → 3-deoxy-3-[18F]fluoro-O-methyl-myo-inositol

Conditions	Yield
With 18F-fluoride; diethylamino-sulfur trifluoride In chloroform for 0.5h; Ambient temperature;	10.6%

quebrachitol (642-38-6) → (1S)-1,3,4,5,6-penta-O-nitro-2-O-methyl-asymm.-inositol (28079-67-6, 134356-41-5)

Conditions	Yield
With sulfuric acid; nitric acid

quebrachitol (642-38-6) → chiro-inositol (18685-70-6)

Conditions	Yield
With hydrogenchloride; acetic acid at 160℃; Kochen des Reaktionsprodukts mit Wasser und Ba(OH)2;

chloro-trimethyl-silane (75-77-4) + quebrachitol (642-38-6) → (2S,3R,5R,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

1-ethoxycyclohexene (1122-84-5) + quebrachitol (642-38-6) → L-3,4:5.6-di-O-cyclohexylidene-2-O-methyl-(-)-chiro-inositol (6848-53-9)

Conditions	Yield
With toluene-4-sulfonic acid In N,N-dimethyl-formamide

quebrachitol (642-38-6) → D-3-deoxy-3-fluoro-1-O-methyl-myo-inositol (125290-98-4) + (1S,2S,3R,4S,5S,6S)-1-fluoro-2-O-(methyl)cyclohexane-2,3,4,5,6-pentol (125290-99-5)

Conditions	Yield
With diethylamino-sulfur trifluoride at 20℃; for 0.75h; Yield given;

quebrachitol (642-38-6) + 2,2-dimethoxy-propane (77-76-9) → 1L-3,4,:5,6-di-O-isopropylidene-2-O-methyl-chiro-inositol (58769-23-6)

quebrachitol (642-38-6) + cyclohexanone (108-94-1) → L-3,4:5.6-di-O-cyclohexylidene-2-O-methyl-(-)-chiro-inositol (6848-53-9)

Conditions	Yield
With toluene-4-sulfonic acid In benzene
With sulfuric acid In N,N-dimethyl-formamide; benzene

quebrachitol (642-38-6) → bornesitol (484-68-4, 484-69-5, 523-92-2, 642-38-6, 3559-00-0, 3564-07-6, 6090-97-7, 7586-49-4, 7600-53-5, 10284-63-6, 17405-65-1, 22350-68-1, 23887-12-9, 32934-27-3, 35688-46-1, 56782-15-1, 58769-21-4, 60537-25-9, 64314-40-5, 74560-60-4, 103773-59-7, 111059-09-7, 115888-70-5, 144902-49-8, 484-71-9)

Conditions	Yield
With sulfuric acid; acetic acid Heating; Irradiation;

quebrachitol (642-38-6) → 3-O-Methyl-D-myo-inosose-(1) (3559-01-1, 5834-35-5, 20095-97-0, 92541-30-5, 92541-35-0, 92541-36-1)

Conditions	Yield
With oxygen; platinum on activated charcoal In water

hydrogenchloride (7647-01-0) + quebrachitol (642-38-6) + acetic acid (64-19-7) → chiro-inositol (18685-70-6)

Conditions	Yield
at 160℃; Kochen des Reaktionsprodukts mit Ba(OH)2 in Wasser;

quebrachitol (642-38-6) → 1L-1,2-di-O-methyl-chiro-inositol

Conditions	Yield
Multi-step reaction with 3 steps 1: 71 percent / p-TsOH*H2O / dimethylformamide / 22.5 h / 20 - 105 °C 2: 94 percent / NaH / dimethylformamide / 0 - 20 °C 3: 71 percent / aq. HCl / methanol / 20 °C View Scheme

quebrachitol (642-38-6) → 1L-3,4:5,6-di-O-cyclohexylidene-1,2-di-O-methyl-chiro-inositol (904689-58-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: 71 percent / p-TsOH*H2O / dimethylformamide / 22.5 h / 20 - 105 °C 2: 94 percent / NaH / dimethylformamide / 0 - 20 °C View Scheme

quebrachitol (642-38-6) → 1L-1-O-benzoyl-3,4:5,6-di-O-cyclohexylidene-2-O-methyl-chiro-inositol (60504-85-0, 128442-40-0, 131432-85-4, 131432-88-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: 71 percent / p-TsOH*H2O / dimethylformamide / 22.5 h / 20 - 105 °C 2: 98 percent / DMAP; Et3N / CH2Cl2 / 120 h / 20 °C View Scheme

quebrachitol (642-38-6) → 1-O-benzoyl-2-O-methyl-(-)-chiro-inositol (725273-54-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: 71 percent / p-TsOH*H2O / dimethylformamide / 22.5 h / 20 - 105 °C 2: 98 percent / DMAP; Et3N / CH2Cl2 / 120 h / 20 °C 3: 88 percent / aq. HCl / acetone; H2O / 48 h / 20 °C View Scheme

quebrachitol (642-38-6) → D-1-O-cyclohexylcarbamoyl-2-deoxy-5,6-O-ethylidene-2-fluoro-3-O-methyl-chiro-inositol

Conditions	Yield
Multi-step reaction with 3 steps 1.1: diethylaminosulfur trifluoride / CH2Cl2 / 4 h / 20 °C 2.1: 61 percent / 1,2-dichloro-ethane / 6 h / Heating 3.1: H2 / Raney-Nickel / ethanol / 8 h / 20 °C 3.2: triethylamine / ethanol / 8 h / 20 °C View Scheme

quebrachitol (642-38-6) → D-1-O-cyclohexylcarbamoyl-2-deoxy-5,6-O-ethylidene-2-fluoro-3-O-methyl-chiro-inositol

Conditions	Yield
Multi-step reaction with 3 steps 1.1: diethylaminosulfur trifluoride / CH2Cl2 / 4 h / 20 °C 2.1: 61 percent / 1,2-dichloro-ethane / 6 h / Heating 3.1: H2 / Raney-Nickel / ethanol / 8 h / 20 °C 3.2: triethylamine / ethanol / 8 h / 20 °C View Scheme

quebrachitol (642-38-6) → D-5,6-O-(2-chloroethylidene)D-1-O-cyclohexylcarbamoyl-2-deoxy-2-fluoro-3-O-methyl-chiro-inositol

Conditions	Yield
Multi-step reaction with 3 steps 1.1: diethylaminosulfur trifluoride / CH2Cl2 / 4 h / 20 °C 2.1: 61 percent / 1,2-dichloro-ethane / 6 h / Heating 3.1: H2 / Raney-Nickel / ethanol / 8 h / 20 °C 3.2: triethylamine / ethanol / 8 h / 20 °C View Scheme

quebrachitol (642-38-6) → D-5,6-O-(2-chloroethylidene)-1-O-cyclohexylcarbamoyl-2-deoxy-2-fluoro-3-O-methyl-chiro-inositol

Conditions	Yield
Multi-step reaction with 3 steps 1.1: diethylaminosulfur trifluoride / CH2Cl2 / 4 h / 20 °C 2.1: 61 percent / 1,2-dichloro-ethane / 6 h / Heating 3.1: H2 / Raney-Nickel / ethanol / 8 h / 20 °C 3.2: triethylamine / ethanol / 8 h / 20 °C View Scheme

Upstream product

• 111392-29-1 (3aS,4S,4aS,7aS,8S,8aR)-4-Allyloxy-8-methoxy-2,2,6,6-tetramethyl-hexahydro-benzo[1,2-d;4,5-d']bis[1,3]dioxole 
• 111015-71-5 (1α,2α,5β,6Sb)-5,6-epoxy-3-cyclohexene-1,2-diol dibenzoate 
• 86504-06-5 cis-3,5-cyclohexadiene-1,2-diol dibenzoate 
• 17793-95-2 cis-1,2-dihydrocatechol 
• 71-43-2 benzene 
• 98510-20-4 myo-Inositol orthoformate 
• 124647-07-0 C₂₁H₂₂O₈ 
• 111392-26-8 (3aS,4S,4aR,7aR,8S,8aR)-4-Methoxy-8-(4-methoxy-benzyloxy)-2,2,6,6-tetramethyl-hexahydro-benzo[1,2-d;4,5-d']bis[1,3]dioxole 
• 111392-30-4 1-O-allyl-4-O-methyl-myo-inositol 
• 111015-73-7 DL-1,2-di-O-methyl-chiro-inositol 
• 111015-74-8 DL-1,3-di-O-benzoyl-4-O-methyl-chiro-inositol 
• 111015-72-6 (1α,2β,3β,6β)-6-methoxy-4-cyclohexene-1,2,3-triol 2,3-dibenzoate 
• 80971-00-2 (3aR,4S,5S,6R,7S,7aR)-4,5,7-Tris-benzyloxy-6-methoxy-2,2-dimethyl-hexahydro-benzo[1,3]dioxole 
• 111446-91-4 (+/-)-1,2,4-tri-O-benzyl-5,6-O-isopropylidene-myo-inositol 

Downstream Products

• 73803-06-2 L-1,3,4,5,6-penta-O-benzoyl-2-O-methyl-chiro-inositol 
• 484-68-4 bornesitol 
• 3559-01-1 3-O-Methyl-D-myo-inosose-⁽¹⁾ 
• 6848-53-9 L-3,4:5.6-di-O-cyclohexylidene-2-O-methyl-(-)-chiro-inositol 
• 754197-57-4 1L-1,2-O-cyclohexylidene-5-O-methyl-chiro-inositol 
• 60504-85-0 1L-1-O-benzoyl-3,4:5,6-di-O-cyclohexylidene-2-O-methyl-chiro-inositol 
• 725273-54-1 1-O-benzoyl-2-O-methyl-(-)-chiro-inositol 
• 341524-06-9 C₃₅H₃₀O₁₀ 
• 148888-46-4 Phosphoric acid dibenzyl ester (1R,2S,3R,4R,6R)-2-benzyloxy-3,4-bis-(bis-benzyloxy-phosphoryloxy)-6-(1-ethoxy-ethoxy)-cyclohexyl ester 
• 148888-44-2 1D-1,4,5-tri-O-benzoyl-6-O-benzyl-3-deoxy-2-O-(1-ethoxyethyl)-myo-inositol 
• 148888-43-1 1D-1,4,5-tri-O-benzoyl-6-O-benzyl-3-deoxy-myo-inositol 

Relevant articles and documents

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.

An effective strategy for the synthesis of 6-O-(2-amino-2-deoxy-α-D-glucopyranosyl)-D-chiro- and -D-myo-inositol 1-phosphate related to putative insulin mimetics

Two glycosylinositol phosphates related to putative insulin mimetics, 6-O-(2-amino-2-deoxy-α-D-glucopyranosyl)-D-chiro-inositol 1-phosphate (1) and 6-O-(2-amino-2-deoxy-α-D-glucopyranosyl)-D-myo-inositol 1-phosphate (2), have been synthesized from selectively protected and enantiomerically pure D-chiro- and myo-inositol derivatives. The D-chiro-inositol unit was prepared in a multigram scale from D-glucose using the Ferrier's carbocyclization route, and it was transformed into the corresponding myo epimer by an oxidation-reduction sequence. The trichloroacetimidate method was applied efficiently for the key glycosylation of the inositol derivatives.

Mikrobial Oxidation in Synthesis: Preparation of (+)- and (-)-Pinitol from Benzene

Microbial oxidation with Pseudomonas putida of benzene affords cis-1,2-dihydroxycyclohexa-3,5-diene (2) which may be converted in five steps and 49percent overall yield to (+/-)-pinitol.Resolution of an intermediate alcohol (6) with menthoxyacetyl chloride provides optically pure materials which may be independently transformed to (+)- or (-)-pinitol.Demethylation conditions for pinitol together with further reactions of (2) and related compounds were investigated.